diff --git a/milatools/cli/commands.py b/milatools/cli/commands.py
index 37afa78d..0a0b76fb 100644
--- a/milatools/cli/commands.py
+++ b/milatools/cli/commands.py
@@ -24,12 +24,13 @@
 from urllib.parse import urlencode
 
 import questionary as qn
-from invoke.exceptions import UnexpectedExit
 from typing_extensions import TypedDict
 
 from ..version import version as mversion
 from .init_command import (
-    create_ssh_keypair,
+    print_welcome_message,
+    setup_keys_on_login_node,
+    setup_passwordless_ssh_access,
     setup_ssh_config,
     setup_vscode_settings,
     setup_windows_ssh_config_from_wsl,
@@ -47,13 +48,13 @@
     randname,
     running_inside_WSL,
     with_control_file,
-    yn,
 )
 
-logger = get_logger(__name__)
 if typing.TYPE_CHECKING:
     from typing_extensions import Unpack
 
+logger = get_logger(__name__)
+
 
 def main():
     if sys.platform != "win32" and get_fully_qualified_name().endswith(
@@ -139,12 +140,12 @@ def mila():
     intranet_parser.set_defaults(function=intranet)
 
     # ----- mila init ------
-
     init_parser = subparsers.add_parser(
         "init",
         help="Set up your configuration and credentials.",
         formatter_class=SortingHelpFormatter,
     )
+
     init_parser.set_defaults(function=init)
 
     # ----- mila forward ------
@@ -396,7 +397,6 @@ def init():
     print("Checking ssh config")
 
     ssh_config = setup_ssh_config()
-    print("# OK")
 
     # if we're running on WSL, we actually just copy the id_rsa + id_rsa.pub and the
     # ~/.ssh/config to the Windows ssh directory (taking care to remove the
@@ -405,116 +405,14 @@ def init():
     if running_inside_WSL():
         setup_windows_ssh_config_from_wsl(linux_ssh_config=ssh_config)
 
-    setup_passwordless_ssh_access()
+    success = setup_passwordless_ssh_access(ssh_config=ssh_config)
+    if not success:
+        exit()
     setup_keys_on_login_node()
     setup_vscode_settings()
     print_welcome_message()
 
 
-def setup_passwordless_ssh_access():
-    print("Checking passwordless authentication")
-
-    here = Local()
-
-    # Check that there is an id file
-    ssh_private_key_path = Path.home() / ".ssh" / "id_rsa"
-
-    sshdir = os.path.expanduser("~/.ssh")
-    if not any(
-        entry.startswith("id") and entry.endswith(".pub")
-        for entry in os.listdir(sshdir)
-    ):
-        if yn("You have no public keys. Generate one?"):
-            # Run ssh-keygen with the given location and no passphrase.
-            create_ssh_keypair(ssh_private_key_path, here)
-        else:
-            exit("No public keys.")
-
-    # Check that it is possible to connect using the key
-
-    if not here.check_passwordless("mila"):
-        if yn(
-            "Your public key does not appear be registered on the cluster. Register it?"
-        ):
-            # NOTE: If we're on a Windows machine, we do something different here:
-            if sys.platform == "win32":
-                command = (
-                    "powershell.exe type $env:USERPROFILE\\.ssh\\id_rsa.pub | ssh mila "
-                    '"cat >> ~/.ssh/authorized_keys"'
-                )
-                here.run(command)
-            else:
-                here.run("ssh-copy-id", "mila")
-            if not here.check_passwordless("mila"):
-                exit("ssh-copy-id appears to have failed")
-        else:
-            exit("No passwordless login.")
-
-
-def setup_keys_on_login_node():
-    print("Checking connection to compute nodes")
-
-    remote = Remote("mila")
-    try:
-        pubkeys = remote.get_lines("ls -t ~/.ssh/id*.pub")
-        print("# OK")
-    except UnexpectedExit:
-        print("# MISSING")
-        if yn("You have no public keys on the login node. Generate them?"):
-            # print("(Note: You can just press Enter 3x to accept the defaults)")
-            # _, keyfile = remote.extract(
-            #     "ssh-keygen",
-            #     pattern="Your public key has been saved in ([^ ]+)",
-            #     wait=True,
-            # )
-            private_file = "~/.ssh/id_rsa"
-            remote.run(f'ssh-keygen -q -t rsa -N "" -f {private_file}')
-            pubkeys = [f"{private_file}.pub"]
-        else:
-            exit("Cannot proceed because there is no public key")
-
-    common = remote.with_bash().get_output(
-        "comm -12 <(sort ~/.ssh/authorized_keys) <(sort ~/.ssh/*.pub)"
-    )
-    if common:
-        print("# OK")
-    else:
-        print("# MISSING")
-        if yn(
-            "To connect to a compute node from a login node you need one id_*.pub to "
-            "be in authorized_keys. Do it?"
-        ):
-            pubkey = pubkeys[0]
-            remote.run(f"cat {pubkey} >> ~/.ssh/authorized_keys")
-        else:
-            exit("You will not be able to SSH to a compute node")
-
-
-def print_welcome_message():
-    print(T.bold_cyan("=" * 60))
-    print(T.bold_cyan("Congrats! You are now ready to start working on the cluster!"))
-    print(T.bold_cyan("=" * 60))
-    print(T.bold("To connect to a login node:"))
-    print("    ssh mila")
-    print(T.bold("To allocate and connect to a compute node:"))
-    print("    ssh mila-cpu")
-    print(T.bold("To open a directory on the cluster with VSCode:"))
-    print("    mila code path/to/code/on/cluster")
-    print(T.bold("Same as above, but allocate 1 GPU, 4 CPUs, 32G of RAM:"))
-    print("    mila code path/to/code/on/cluster --alloc --gres=gpu:1 --mem=32G -c 4")
-    print()
-    print(
-        "For more information, read the milatools documentation at",
-        T.bold_cyan("https://github.com/mila-iqia/milatools"),
-        "or run `mila --help`.",
-        "Also make sure you read the Mila cluster documentation at",
-        T.bold_cyan("https://docs.mila.quebec/"),
-        "and join the",
-        T.bold_green("#mila-cluster"),
-        "channel on Slack.",
-    )
-
-
 def forward(
     remote: str,
     page: str | None,
diff --git a/milatools/cli/init_command.py b/milatools/cli/init_command.py
index 3f11fd9f..5dbfc9fe 100644
--- a/milatools/cli/init_command.py
+++ b/milatools/cli/init_command.py
@@ -2,7 +2,9 @@
 
 import copy
 import difflib
+import functools
 import json
+import shlex
 import shutil
 import subprocess
 import sys
@@ -12,8 +14,10 @@
 from typing import Any
 
 import questionary as qn
+from invoke.exceptions import UnexpectedExit
 
-from .local import Local
+from .local import Local, check_passwordless
+from .remote import Remote
 from .utils import SSHConfig, T, running_inside_WSL, yn
 from .vscode_utils import (
     get_expected_vscode_settings_json_path,
@@ -23,8 +27,88 @@
 logger = get_logger(__name__)
 
 WINDOWS_UNSUPPORTED_KEYS = ["ControlMaster", "ControlPath", "ControlPersist"]
-HOSTS = ["mila", "mila-cpu", "*.server.mila.quebec !*login.server.mila.quebec"]
-"""List of host entries that get added to the SSH configuration by `mila init`."""
+
+
+if sys.platform == "win32":
+    ssh_multiplexing_config = {}
+else:
+    ssh_multiplexing_config = {
+        # Tries to reuse an existing connection, but if it fails, it will create a
+        # new one.
+        "ControlMaster": "auto",
+        # This makes a file per connection, like
+        # normandf@login.server.mila.quebec:2222
+        "ControlPath": r"~/.cache/ssh/%r@%h:%p",
+        # persist for 10 minutes after the last connection ends.
+        "ControlPersist": 600,
+    }
+
+
+MILA_ENTRIES: dict[str, dict[str, int | str]] = {
+    "mila": {
+        "HostName": "login.server.mila.quebec",
+        # "User": mila_username,
+        "PreferredAuthentications": "publickey,keyboard-interactive",
+        "Port": 2222,
+        "ServerAliveInterval": 120,
+        "ServerAliveCountMax": 5,
+        **ssh_multiplexing_config,
+    },
+    "mila-cpu": {
+        # "User": mila_username,
+        "Port": 2222,
+        "ForwardAgent": "yes",
+        "StrictHostKeyChecking": "no",
+        "LogLevel": "ERROR",
+        "UserKnownHostsFile": "/dev/null",
+        "RequestTTY": "force",
+        "ConnectTimeout": 600,
+        "ServerAliveInterval": 120,
+        # NOTE: will not work with --gres prior to Slurm 22.05, because srun --overlap
+        # cannot share gpus
+        "ProxyCommand": (
+            'ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh '
+            'mila-cpu --mem=8G"'
+        ),
+        "RemoteCommand": (
+            "/cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu"
+        ),
+    },
+    "*.server.mila.quebec !*login.server.mila.quebec": {
+        "HostName": "%h",
+        # "User": mila_username,
+        "ProxyJump": "mila",
+        **ssh_multiplexing_config,
+    },
+}
+DRAC_CLUSTERS = ["beluga", "cedar", "graham", "narval"]
+DRAC_ENTRIES: dict[str, dict[str, int | str]] = {
+    "beluga cedar graham narval niagara": {
+        "Hostname": "%h.alliancecan.ca",
+        # User=drac_username,
+        **ssh_multiplexing_config,
+    },
+    "!beluga  bc????? bg????? bl?????": {
+        "ProxyJump": "beluga",
+        # User=drac_username,
+    },
+    "!cedar   cdr? cdr?? cdr??? cdr????": {
+        "ProxyJump": "cedar",
+        # User=drac_username,
+    },
+    "!graham  gra??? gra????": {
+        "ProxyJump": "graham",
+        # User=drac_username,
+    },
+    "!narval  nc????? ng?????": {
+        "ProxyJump": "narval",
+        # User=drac_username,
+    },
+    "!niagara nia????": {
+        "ProxyJump": "niagara",
+        # User=drac_username,
+    },
+}
 
 
 def setup_ssh_config(
@@ -44,96 +128,39 @@ def setup_ssh_config(
     - "*.server.mila.quebec !*login.server.mila.quebec": Sets some useful attributes for
       connecting directly to compute nodes.
 
-    TODO: Also ask if we should add entries for the ComputeCanada/DRAC clusters.
-
     Returns:
         The resulting SSHConfig if the changes are approved.
     """
 
     ssh_config_path = _setup_ssh_config_file(ssh_config_path)
     ssh_config = SSHConfig(ssh_config_path)
-    username: str = _get_username(ssh_config)
+    mila_username: str = _get_mila_username(ssh_config)
+    drac_username: str | None = _get_drac_username(ssh_config)
     orig_config = ssh_config.cfg.config()
 
-    control_path_dir = Path("~/.cache/ssh")
-    # note: a bit nicer to keep the "~" in the path in the ssh config file, but we need
-    # to make sure that the directory actually exists.
-    control_path_dir.expanduser().mkdir(exist_ok=True, parents=True)
+    for hostname, entry in MILA_ENTRIES.copy().items():
+        entry.update(User=mila_username)
+        _add_ssh_entry(ssh_config, hostname, entry)
+        _make_controlpath_dir(entry)
 
-    if sys.platform == "win32":
-        ssh_multiplexing_config = {}
-    else:
-        ssh_multiplexing_config = {
-            # Tries to reuse an existing connection, but if it fails, it will create a
-            # new one.
-            "ControlMaster": "auto",
-            # This makes a file per connection, like
-            # normandf@login.server.mila.quebec:2222
-            "ControlPath": str(control_path_dir / r"%r@%h:%p"),
-            # persist for 10 minutes after the last connection ends.
-            "ControlPersist": 600,
-        }
-
-    _add_ssh_entry(
-        ssh_config,
-        host="mila",
-        HostName="login.server.mila.quebec",
-        User=username,
-        PreferredAuthentications="publickey,keyboard-interactive",
-        Port=2222,
-        ServerAliveInterval=120,
-        ServerAliveCountMax=5,
-        **ssh_multiplexing_config,
-    )
-
-    _add_ssh_entry(
-        ssh_config,
-        "mila-cpu",
-        User=username,
-        Port=2222,
-        ForwardAgent="yes",
-        StrictHostKeyChecking="no",
-        LogLevel="ERROR",
-        UserKnownHostsFile="/dev/null",
-        RequestTTY="force",
-        ConnectTimeout=600,
-        ServerAliveInterval=120,
-        # NOTE: will not work with --gres prior to Slurm 22.05, because srun --overlap
-        # cannot share it
-        ProxyCommand=(
-            'ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh '
-            'mila-cpu --mem=8G"'
-        ),
-        RemoteCommand=(
-            "/cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu"
-        ),
-    )
+    if drac_username:
+        logger.debug(
+            f"Adding entries for the ComputeCanada/DRAC clusters to {ssh_config_path}."
+        )
+        for hostname, entry in DRAC_ENTRIES.copy().items():
+            entry.update(User=drac_username)
+            _add_ssh_entry(ssh_config, hostname, entry)
+            _make_controlpath_dir(entry)
 
     # Check for *.server.mila.quebec in ssh config, to connect to compute nodes
-
     old_cnode_pattern = "*.server.mila.quebec"
-    cnode_pattern = "*.server.mila.quebec !*login.server.mila.quebec"
 
     if old_cnode_pattern in ssh_config.hosts():
-        if yn(
-            "The '*.server.mila.quebec' entry in ~/.ssh/config is too general and "
-            "should exclude login.server.mila.quebec. Fix this?"
-        ):
-            if cnode_pattern in ssh_config.hosts():
-                ssh_config.remove(old_cnode_pattern)
-            else:
-                ssh_config.rename(old_cnode_pattern, cnode_pattern)
-    else:
-        _add_ssh_entry(
-            ssh_config,
-            cnode_pattern,
-            HostName="%h",
-            User=username,
-            ProxyJump="mila",
-            ForwardAgent="yes",
-            ForwardX11="yes",
-            **ssh_multiplexing_config,
+        logger.info(
+            f"The '{old_cnode_pattern}' entry in ~/.ssh/config is too general and "
+            "should exclude login.server.mila.quebec. Fixing this."
         )
+        ssh_config.remove(old_cnode_pattern)
 
     new_config = ssh_config.cfg.config()
     if orig_config == new_config:
@@ -200,6 +227,174 @@ def setup_windows_ssh_config_from_wsl(linux_ssh_config: SSHConfig):
         _copy_if_needed(linux_key_file, windows_key_file)
 
 
+def setup_passwordless_ssh_access(ssh_config: SSHConfig) -> bool:
+    """Sets up passwordless ssh access to the Mila and optionally also to DRAC.
+
+    Sets up ssh connection to the DRAC clusters if they are present in the SSH config
+    file.
+
+    Returns whether the operation completed successfully or not.
+    """
+    print("Checking passwordless authentication")
+
+    here = Local()
+    sshdir = Path.home() / ".ssh"
+    ssh_private_key_path = Path.home() / ".ssh" / "id_rsa"
+
+    # Check if there is a public key file in ~/.ssh
+    if not list(sshdir.glob("id*.pub")):
+        if yn("You have no public keys. Generate one?"):
+            # Run ssh-keygen with the given location and no passphrase.
+            create_ssh_keypair(ssh_private_key_path, here)
+        else:
+            print("No public keys.")
+            return False
+
+    success = setup_passwordless_ssh_access_to_cluster("mila")
+    if not success:
+        return False
+
+    drac_clusters_in_ssh_config: list[str] = []
+    hosts_in_config = ssh_config.hosts()
+    for cluster in DRAC_CLUSTERS:
+        if any(cluster in hostname for hostname in hosts_in_config):
+            drac_clusters_in_ssh_config.append(cluster)
+
+    if not drac_clusters_in_ssh_config:
+        logger.debug(
+            f"There are no DRAC clusters in the SSH config at {ssh_config.path}."
+        )
+        return True
+
+    print(
+        "Setting up passwordless ssh access to the DRAC clusters with ssh-copy-id.\n"
+        "\n"
+        "Please note that you can also setup passwordless SSH access to all the DRAC "
+        "clusters by visiting https://ccdb.alliancecan.ca/ssh_authorized_keys and "
+        "copying in the content of your public key in the box.\n"
+        "See https://docs.alliancecan.ca/wiki/SSH_Keys#Using_CCDB for more info."
+    )
+    for drac_cluster in drac_clusters_in_ssh_config:
+        success = setup_passwordless_ssh_access_to_cluster(drac_cluster)
+        if not success:
+            return False
+    return True
+
+
+def setup_passwordless_ssh_access_to_cluster(cluster: str) -> bool:
+    """Sets up passwordless SSH access to the given hostname.
+
+    On Mac/Linux, uses `ssh-copy-id`. Performs the steps of ssh-copy-id manually on
+    Windows.
+
+    Returns whether the operation completed successfully or not.
+    """
+    here = Local()
+    # Check that it is possible to connect without using a password.
+    print(f"Checking if passwordless SSH access is setup for the {cluster} cluster.")
+    # TODO: Potentially use the public key from the SSH config file instead of
+    # the default. It's also possible that ssh-copy-id selects the key from the
+    # config file, I'm not sure.
+    # ssh_private_key_path = Path.home() / ".ssh" / "id_rsa"
+
+    if check_passwordless(cluster):
+        logger.info(f"Passwordless SSH access to {cluster} is already setup correctly.")
+        return True
+
+    if not yn(
+        f"Your public key does not appear be registered on the {cluster} cluster. "
+        "Register it?"
+    ):
+        print("No passwordless login.")
+        return False
+
+    print("Please enter your password when prompted.")
+    if sys.platform == "win32":
+        # todo: the path to the key is hard-coded here.
+        command = (
+            "powershell.exe",
+            "type",
+            "$env:USERPROFILE\\.ssh\\id_rsa.pub",
+            "|",
+            "ssh",
+            "-o",
+            "StrictHostKeyChecking=no",
+            cluster,
+            '"cat >> ~/.ssh/authorized_keys"',
+        )
+        here.run(*command, check=True)
+    else:
+        here.run("ssh-copy-id", "-o", "StrictHostKeyChecking=no", cluster, check=True)
+
+    # double-check that this worked.
+    if not check_passwordless(cluster):
+        print(f"'ssh-copy-id {cluster}' appears to have failed!")
+        return False
+    return True
+
+
+def setup_keys_on_login_node():
+    #####################################
+    # Step 3: Set up keys on login node #
+    #####################################
+
+    print("Checking connection to compute nodes")
+
+    remote = Remote("mila")
+    try:
+        pubkeys = remote.get_lines("ls -t ~/.ssh/id*.pub")
+        print("# OK")
+    except UnexpectedExit:
+        print("# MISSING")
+        if yn("You have no public keys on the login node. Generate them?"):
+            private_file = "~/.ssh/id_rsa"
+            remote.run(f'ssh-keygen -q -t rsa -N "" -f {private_file}')
+            pubkeys = [f"{private_file}.pub"]
+        else:
+            exit("Cannot proceed because there is no public key")
+
+    common = remote.with_bash().get_output(
+        "comm -12 <(sort ~/.ssh/authorized_keys) <(sort ~/.ssh/*.pub)"
+    )
+    if common:
+        print("# OK")
+    else:
+        print("# MISSING")
+        if yn(
+            "To connect to a compute node from a login node you need one id_*.pub to "
+            "be in authorized_keys. Do it?"
+        ):
+            pubkey = pubkeys[0]
+            remote.run(f"cat {pubkey} >> ~/.ssh/authorized_keys")
+        else:
+            exit("You will not be able to SSH to a compute node")
+
+
+def print_welcome_message():
+    print(T.bold_cyan("=" * 60))
+    print(T.bold_cyan("Congrats! You are now ready to start working on the cluster!"))
+    print(T.bold_cyan("=" * 60))
+    print(T.bold("To connect to a login node:"))
+    print("    ssh mila")
+    print(T.bold("To allocate and connect to a compute node:"))
+    print("    ssh mila-cpu")
+    print(T.bold("To open a directory on the cluster with VSCode:"))
+    print("    mila code path/to/code/on/cluster")
+    print(T.bold("Same as above, but allocate 1 GPU, 4 CPUs, 32G of RAM:"))
+    print("    mila code path/to/code/on/cluster --alloc --gres=gpu:1 --mem=32G -c 4")
+    print()
+    print(
+        "For more information, read the milatools documentation at",
+        T.bold_cyan("https://github.com/mila-iqia/milatools"),
+        "or run `mila --help`.",
+        "Also make sure you read the Mila cluster documentation at",
+        T.bold_cyan("https://docs.mila.quebec/"),
+        "and join the",
+        T.bold_green("#mila-cluster"),
+        "channel on Slack.",
+    )
+
+
 def _copy_if_needed(linux_key_file: Path, windows_key_file: Path):
     if linux_key_file.exists() and not windows_key_file.exists():
         print(
@@ -216,7 +411,11 @@ def get_windows_home_path_in_wsl() -> Path:
 
 
 def create_ssh_keypair(ssh_private_key_path: Path, local: Local) -> None:
-    local.run("ssh-keygen", "-f", str(ssh_private_key_path), "-t", "rsa", "-N=''")
+    local.run(
+        *shlex.split(
+            f'ssh-keygen -f {shlex.quote(str(ssh_private_key_path))} -t rsa -N=""'
+        ),
+    )
 
 
 def setup_vscode_settings():
@@ -240,25 +439,34 @@ def setup_vscode_settings():
             )
         )
         return
-
+    vscode_settings_json_path = get_expected_vscode_settings_json_path()
     try:
-        _update_vscode_settings_json({"remote.SSH.connectTimeout": 60})
+        _update_vscode_settings_json(
+            vscode_settings_json_path, new_values={"remote.SSH.connectTimeout": 60}
+        )
     except Exception as err:
         logger.warning(
-            f"Unable to setup VsCode settings for remote development: {err}\n"
-            f"Skipping and leaving the settings unchanged.",
+            T.orange(
+                f"Unable to setup VsCode settings file at {vscode_settings_json_path} "
+                f"for remote development.\n"
+                f"Skipping and leaving the settings unchanged."
+            ),
             exc_info=err,
         )
 
 
-def _update_vscode_settings_json(new_values: dict[str, Any]) -> None:
-    vscode_settings_json_path = get_expected_vscode_settings_json_path()
-
+def _update_vscode_settings_json(
+    vscode_settings_json_path: Path, new_values: dict[str, Any]
+) -> None:
     settings_json: dict[str, Any] = {}
     if vscode_settings_json_path.exists():
         logger.info(f"Reading VsCode settings from {vscode_settings_json_path}")
         with open(vscode_settings_json_path) as f:
-            settings_json = json.load(f)
+            settings_json = json.loads(
+                "\n".join(
+                    line for line in f.readlines() if not line.strip().startswith("#")
+                )
+            )
 
     settings_before = copy.deepcopy(settings_json)
     settings_json.update(
@@ -338,7 +546,7 @@ def _confirm_changes(ssh_config: SSHConfig, previous: str) -> bool:
     return ask_to_confirm_changes(before, after, ssh_config.path)
 
 
-def _get_username(ssh_config: SSHConfig) -> str:
+def _get_mila_username(ssh_config: SSHConfig) -> str:
     # Check for a mila entry in ssh config
     # NOTE: This also supports the case where there's a 'HOST mila some_alias_for_mila'
     # entry.
@@ -359,14 +567,47 @@ def _get_username(ssh_config: SSHConfig) -> str:
     while not username:
         username = qn.text(
             "What's your username on the mila cluster?\n",
-            validate=_is_valid_username,
+            validate=functools.partial(_is_valid_username, cluster_name="mila cluster"),
         ).unsafe_ask()
     return username.strip()
 
 
-def _is_valid_username(text: str) -> bool | str:
+def _get_drac_username(ssh_config: SSHConfig) -> str | None:
+    """Retrieve or ask the user for their username on the ComputeCanada/DRAC
+    clusters."""
+    # Check for one of the DRAC entries in ssh config
+    username: str | None = None
+    hosts_with_cluster_in_name_and_a_user_entry = [
+        host
+        for host in ssh_config.hosts()
+        if any(
+            cc_cluster in host.split() or f"!{cc_cluster}" in host.split()
+            for cc_cluster in DRAC_CLUSTERS
+        )
+        and "user" in ssh_config.host(host)
+    ]
+    users_from_drac_config_entries = set(
+        ssh_config.host(host)["user"]
+        for host in hosts_with_cluster_in_name_and_a_user_entry
+    )
+    # Note: If there are none, or more than one, then we'll ask the user for their
+    # username, just to be sure.
+    if len(users_from_drac_config_entries) == 1:
+        username = users_from_drac_config_entries.pop()
+    elif yn("Do you also have an account on the ComputeCanada/DRAC clusters?"):
+        while not username:
+            username = qn.text(
+                "What's your username on the CC/DRAC clusters?\n",
+                validate=functools.partial(
+                    _is_valid_username, cluster_name="ComputeCanada/DRAC clusters"
+                ),
+            ).unsafe_ask()
+    return username.strip() if username else None
+
+
+def _is_valid_username(text: str, cluster_name: str = "mila cluster") -> bool | str:
     return (
-        "Please enter your username on the mila cluster."
+        f"Please enter your username on the {cluster_name}."
         if not text or text.isspace()
         else True
     )
@@ -381,22 +622,27 @@ def _is_valid_username(text: str) -> bool | str:
 def _add_ssh_entry(
     ssh_config: SSHConfig,
     host: str,
-    Host: str | None = None,
+    entry: dict[str, str | int],
     *,
     _space_before: bool = True,
     _space_after: bool = False,
-    **entry,
 ) -> None:
     """Adds or updates an entry in the ssh config object."""
     # NOTE: `Host` is also a parameter to make sure it isn't in `entry`.
-    assert not (host and Host)
-    host = Host or host
+    assert "Host" not in entry
+
+    sorted_by_keys = False
+
     if host in ssh_config.hosts():
         existing_entry = ssh_config.host(host)
         existing_entry.update(entry)
+        if sorted_by_keys:
+            existing_entry = dict(sorted(existing_entry.items()))
         ssh_config.cfg.set(host, **existing_entry)
         logger.debug(f"Updated {host} entry in ssh config at path {ssh_config.path}.")
     else:
+        if sorted_by_keys:
+            entry = dict(sorted(entry.items()))
         ssh_config.add(
             host,
             _space_before=_space_before,
@@ -414,13 +660,15 @@ def _copy_valid_ssh_entries_to_windows_ssh_config_file(
     unsupported_keys_lowercase = set(k.lower() for k in WINDOWS_UNSUPPORTED_KEYS)
 
     # NOTE: need to preserve the ordering of entries:
-    for host in HOSTS + [
-        host for host in linux_ssh_config.hosts() if host not in HOSTS
+    entries_to_move = list(MILA_ENTRIES.keys()) + list(DRAC_ENTRIES.keys())
+    for host in entries_to_move + [
+        host for host in linux_ssh_config.hosts() if host not in entries_to_move
     ]:
         if host not in linux_ssh_config.hosts():
             warnings.warn(
                 RuntimeWarning(
-                    f"Weird, we expected to have a {host!r} entry in the SSH config..."
+                    f"We expected to have a {host!r} entry in the SSH config. "
+                    f"Did you run `mila init`?"
                 )
             )
             continue
@@ -428,9 +676,19 @@ def _copy_valid_ssh_entries_to_windows_ssh_config_file(
         _add_ssh_entry(
             windows_ssh_config,
             host,
-            **{
+            {
                 key: value
                 for key, value in linux_ssh_entry.items()
                 if key.lower() not in unsupported_keys_lowercase
             },
         )
+
+
+def _make_controlpath_dir(entry: dict[str, str | int]) -> None:
+    if "ControlPath" not in entry:
+        return
+    control_path = entry["ControlPath"]
+    assert isinstance(control_path, str)
+    # Create the ControlPath directory if it doesn't exist:
+    control_path_dir = Path(control_path).expanduser().parent
+    control_path_dir.mkdir(exist_ok=True, parents=True)
diff --git a/milatools/cli/local.py b/milatools/cli/local.py
index 9c30ae60..a9a1b73f 100644
--- a/milatools/cli/local.py
+++ b/milatools/cli/local.py
@@ -1,25 +1,29 @@
 from __future__ import annotations
 
-import shlex
 import subprocess
+from logging import getLogger as get_logger
 from subprocess import CompletedProcess
 from typing import IO, Any
 
+import fabric
+import paramiko.ssh_exception
 from typing_extensions import deprecated
 
 from .utils import CommandNotFoundError, T, shjoin
 
+logger = get_logger(__name__)
+
 
 class Local:
     def display(self, args: list[str] | tuple[str, ...]) -> None:
-        print(T.bold_green("(local) $ ", shjoin(args)))
+        display(args)
 
     def silent_get(self, *cmd: str) -> str:
         return subprocess.check_output(cmd, universal_newlines=True)
 
     @deprecated("This isn't used and will probably be removed. Don't start using it.")
     def get(self, *cmd: str) -> str:
-        self.display(cmd)
+        display(cmd)
         return subprocess.check_output(cmd, universal_newlines=True)
 
     def run(
@@ -28,8 +32,10 @@ def run(
         stdout: int | IO[Any] | None = None,
         stderr: int | IO[Any] | None = None,
         capture_output: bool = False,
+        timeout: float | None = None,
+        check: bool = False,
     ) -> CompletedProcess[str]:
-        self.display(cmd)
+        display(cmd)
         try:
             return subprocess.run(
                 cmd,
@@ -37,6 +43,8 @@ def run(
                 stderr=stderr,
                 capture_output=capture_output,
                 universal_newlines=True,
+                timeout=timeout,
+                check=check,
             )
         except FileNotFoundError as e:
             if e.filename == cmd[0]:
@@ -54,20 +62,33 @@ def popen(
             cmd, stdout=stdout, stderr=stderr, universal_newlines=True
         )
 
-    def check_passwordless(self, host: str) -> bool:
-        results = self.run(
-            *shlex.split(f"ssh -oPreferredAuthentications=publickey {host} 'echo OK'"),
-            stdout=subprocess.PIPE,
-            stderr=subprocess.PIPE,
-        )
-        if results.returncode != 0:
-            if "Permission denied" in results.stderr:
-                return False
-            print(results.stdout)
-            print(results.stderr)
-            exit(f"Failed to connect to {host}, could not understand error")
-        # TODO: Perhaps we could actually check the output of the command here!
-        # elif "OK" in results.stdout:
-        else:
-            print("# OK")
-            return True
+    def check_passwordless(self, host: str):
+        return check_passwordless(host)
+
+
+def display(split_command: list[str] | tuple[str, ...]) -> None:
+    print(T.bold_green("(local) $ ", shjoin(split_command)))
+
+
+def check_passwordless(host: str) -> bool:
+    try:
+        with fabric.Connection(host) as connection:
+            results: fabric.runners.Result = connection.run(
+                "echo OK",
+                in_stream=False,
+                echo=True,
+                echo_format=T.bold_cyan(f"({host})" + " $ {command}"),
+            )
+
+    except (
+        paramiko.ssh_exception.SSHException,
+        paramiko.ssh_exception.NoValidConnectionsError,
+    ) as err:
+        logger.debug(f"Unable to connect to {host} without a password: {err}")
+        return False
+
+    if "OK" in results.stdout:
+        return True
+    logger.error("Unexpected output from SSH command, output didn't contain 'OK'!")
+    logger.error(f"stdout: {results.stdout}, stderr: {results.stderr}")
+    return False
diff --git a/poetry.lock b/poetry.lock
index 55014833..57f1544f 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.6.1 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.7.1 and should not be changed by hand.
 
 [[package]]
 name = "alabaster"
@@ -22,66 +22,57 @@ files = [
     {file = "ansicon-1.89.0.tar.gz", hash = "sha256:e4d039def5768a47e4afec8e89e83ec3ae5a26bf00ad851f914d1240b444d2b1"},
 ]
 
-[[package]]
-name = "attrs"
-version = "22.2.0"
-description = "Classes Without Boilerplate"
-optional = false
-python-versions = ">=3.6"
-files = [
-    {file = "attrs-22.2.0-py3-none-any.whl", hash = "sha256:29e95c7f6778868dbd49170f98f8818f78f3dc5e0e37c0b1f474e3561b240836"},
-    {file = "attrs-22.2.0.tar.gz", hash = "sha256:c9227bfc2f01993c03f68db37d1d15c9690188323c067c641f1a35ca58185f99"},
-]
-
-[package.extras]
-cov = ["attrs[tests]", "coverage-enable-subprocess", "coverage[toml] (>=5.3)"]
-dev = ["attrs[docs,tests]"]
-docs = ["furo", "myst-parser", "sphinx", "sphinx-notfound-page", "sphinxcontrib-towncrier", "towncrier", "zope.interface"]
-tests = ["attrs[tests-no-zope]", "zope.interface"]
-tests-no-zope = ["cloudpickle", "cloudpickle", "hypothesis", "hypothesis", "mypy (>=0.971,<0.990)", "mypy (>=0.971,<0.990)", "pympler", "pympler", "pytest (>=4.3.0)", "pytest (>=4.3.0)", "pytest-mypy-plugins", "pytest-mypy-plugins", "pytest-xdist[psutil]", "pytest-xdist[psutil]"]
-
 [[package]]
 name = "babel"
-version = "2.11.0"
+version = "2.14.0"
 description = "Internationalization utilities"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 files = [
-    {file = "Babel-2.11.0-py3-none-any.whl", hash = "sha256:1ad3eca1c885218f6dce2ab67291178944f810a10a9b5f3cb8382a5a232b64fe"},
-    {file = "Babel-2.11.0.tar.gz", hash = "sha256:5ef4b3226b0180dedded4229651c8b0e1a3a6a2837d45a073272f313e4cf97f6"},
+    {file = "Babel-2.14.0-py3-none-any.whl", hash = "sha256:efb1a25b7118e67ce3a259bed20545c29cb68be8ad2c784c83689981b7a57287"},
+    {file = "Babel-2.14.0.tar.gz", hash = "sha256:6919867db036398ba21eb5c7a0f6b28ab8cbc3ae7a73a44ebe34ae74a4e7d363"},
 ]
 
 [package.dependencies]
-pytz = ">=2015.7"
+pytz = {version = ">=2015.7", markers = "python_version < \"3.9\""}
+
+[package.extras]
+dev = ["freezegun (>=1.0,<2.0)", "pytest (>=6.0)", "pytest-cov"]
 
 [[package]]
 name = "bcrypt"
-version = "4.0.1"
+version = "4.1.2"
 description = "Modern password hashing for your software and your servers"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 files = [
-    {file = "bcrypt-4.0.1-cp36-abi3-macosx_10_10_universal2.whl", hash = "sha256:b1023030aec778185a6c16cf70f359cbb6e0c289fd564a7cfa29e727a1c38f8f"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.manylinux_2_24_aarch64.whl", hash = "sha256:08d2947c490093a11416df18043c27abe3921558d2c03e2076ccb28a116cb6d0"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:0eaa47d4661c326bfc9d08d16debbc4edf78778e6aaba29c1bc7ce67214d4410"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:ae88eca3024bb34bb3430f964beab71226e761f51b912de5133470b649d82344"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_24_x86_64.whl", hash = "sha256:a522427293d77e1c29e303fc282e2d71864579527a04ddcfda6d4f8396c6c36a"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_28_aarch64.whl", hash = "sha256:fbdaec13c5105f0c4e5c52614d04f0bca5f5af007910daa8b6b12095edaa67b3"},
-    {file = "bcrypt-4.0.1-cp36-abi3-manylinux_2_28_x86_64.whl", hash = "sha256:ca3204d00d3cb2dfed07f2d74a25f12fc12f73e606fcaa6975d1f7ae69cacbb2"},
-    {file = "bcrypt-4.0.1-cp36-abi3-musllinux_1_1_aarch64.whl", hash = "sha256:089098effa1bc35dc055366740a067a2fc76987e8ec75349eb9484061c54f535"},
-    {file = "bcrypt-4.0.1-cp36-abi3-musllinux_1_1_x86_64.whl", hash = "sha256:e9a51bbfe7e9802b5f3508687758b564069ba937748ad7b9e890086290d2f79e"},
-    {file = "bcrypt-4.0.1-cp36-abi3-win32.whl", hash = "sha256:2caffdae059e06ac23fce178d31b4a702f2a3264c20bfb5ff541b338194d8fab"},
-    {file = "bcrypt-4.0.1-cp36-abi3-win_amd64.whl", hash = "sha256:8a68f4341daf7522fe8d73874de8906f3a339048ba406be6ddc1b3ccb16fc0d9"},
-    {file = "bcrypt-4.0.1-pp37-pypy37_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:bf4fa8b2ca74381bb5442c089350f09a3f17797829d958fad058d6e44d9eb83c"},
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-    {file = "bcrypt-4.0.1-pp38-pypy38_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl", hash = "sha256:cbb03eec97496166b704ed663a53680ab57c5084b2fc98ef23291987b525cb7d"},
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+    {file = "bcrypt-4.1.2-cp37-abi3-macosx_10_12_universal2.whl", hash = "sha256:ac621c093edb28200728a9cca214d7e838529e557027ef0581685909acd28b5e"},
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+    {file = "bcrypt-4.1.2-cp39-abi3-win32.whl", hash = "sha256:02d9ef8915f72dd6daaef40e0baeef8a017ce624369f09754baf32bb32dba25f"},
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+    {file = "bcrypt-4.1.2-pp310-pypy310_pp73-manylinux_2_28_aarch64.whl", hash = "sha256:d75fc8cd0ba23f97bae88a6ec04e9e5351ff3c6ad06f38fe32ba50cbd0d11946"},
+    {file = "bcrypt-4.1.2-pp310-pypy310_pp73-manylinux_2_28_x86_64.whl", hash = "sha256:a97e07e83e3262599434816f631cc4c7ca2aa8e9c072c1b1a7fec2ae809a1d2d"},
+    {file = "bcrypt-4.1.2-pp39-pypy39_pp73-manylinux_2_28_aarch64.whl", hash = "sha256:e51c42750b7585cee7892c2614be0d14107fad9581d1738d954a262556dd1aab"},
+    {file = "bcrypt-4.1.2-pp39-pypy39_pp73-manylinux_2_28_x86_64.whl", hash = "sha256:ba4e4cc26610581a6329b3937e02d319f5ad4b85b074846bf4fef8a8cf51e7bb"},
+    {file = "bcrypt-4.1.2.tar.gz", hash = "sha256:33313a1200a3ae90b75587ceac502b048b840fc69e7f7a0905b5f87fac7a1258"},
 ]
 
 [package.extras]
@@ -90,28 +81,42 @@ typecheck = ["mypy"]
 
 [[package]]
 name = "black"
-version = "23.1a1"
+version = "23.3.0"
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 [package.dependencies]
 click = ">=8.0.0"
 mypy-extensions = ">=0.4.3"
+packaging = ">=22.0"
 pathspec = ">=0.9.0"
 platformdirs = ">=2"
 tomli = {version = ">=1.1.0", markers = "python_version < \"3.11\""}
@@ -126,13 +131,13 @@ uvloop = ["uvloop (>=0.15.2)"]
 
 [[package]]
 name = "blessed"
-version = "1.19.1"
+version = "1.20.0"
 description = "Easy, practical library for making terminal apps, by providing an elegant, well-documented interface to Colors, Keyboard input, and screen Positioning capabilities."
 optional = false
 python-versions = ">=2.7"
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 [package.dependencies]
@@ -142,13 +147,13 @@ wcwidth = ">=0.1.4"
 
 [[package]]
 name = "certifi"
-version = "2022.12.7"
+version = "2023.11.17"
 description = "Python package for providing Mozilla's CA Bundle."
 optional = false
 python-versions = ">=3.6"
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 ]
 
 [[package]]
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+version = "3.3.2"
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 [package.dependencies]
@@ -419,34 +426,34 @@ toml = ["toml"]
 
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+    {file = "cryptography-41.0.7-pp39-pypy39_pp73-win_amd64.whl", hash = "sha256:d6c391c021ab1f7a82da5d8d0b3cee2f4b2c455ec86c8aebbc84837a631ff309"},
+    {file = "cryptography-41.0.7.tar.gz", hash = "sha256:13f93ce9bea8016c253b34afc6bd6a75993e5c40672ed5405a9c832f0d4a00bc"},
 ]
 
 [package.dependencies]
@@ -492,24 +499,24 @@ dev = ["PyTest", "PyTest-Cov", "bump2version (<1)", "sphinx (<2)", "tox"]
 
 [[package]]
 name = "docutils"
-version = "0.17.1"
+version = "0.18.1"
 description = "Docutils -- Python Documentation Utilities"
 optional = false
 python-versions = ">=2.7, !=3.0.*, !=3.1.*, !=3.2.*, !=3.3.*, !=3.4.*"
 files = [
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-    {file = "docutils-0.17.1.tar.gz", hash = "sha256:686577d2e4c32380bb50cbb22f575ed742d58168cee37e99117a854bcd88f125"},
+    {file = "docutils-0.18.1-py2.py3-none-any.whl", hash = "sha256:23010f129180089fbcd3bc08cfefccb3b890b0050e1ca00c867036e9d161b98c"},
+    {file = "docutils-0.18.1.tar.gz", hash = "sha256:679987caf361a7539d76e584cbeddc311e3aee937877c87346f31debc63e9d06"},
 ]
 
 [[package]]
 name = "exceptiongroup"
-version = "1.1.0"
+version = "1.2.0"
 description = "Backport of PEP 654 (exception groups)"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "exceptiongroup-1.1.0-py3-none-any.whl", hash = "sha256:327cbda3da756e2de031a3107b81ab7b3770a602c4d16ca618298c526f4bec1e"},
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+    {file = "exceptiongroup-1.2.0-py3-none-any.whl", hash = "sha256:4bfd3996ac73b41e9b9628b04e079f193850720ea5945fc96a08633c66912f14"},
+    {file = "exceptiongroup-1.2.0.tar.gz", hash = "sha256:91f5c769735f051a4290d52edd0858999b57e5876e9f85937691bd4c9fa3ed68"},
 ]
 
 [package.extras]
@@ -537,29 +544,29 @@ pytest = ["pytest (>=7)"]
 
 [[package]]
 name = "flake8"
-version = "6.0.0"
+version = "6.1.0"
 description = "the modular source code checker: pep8 pyflakes and co"
 optional = false
 python-versions = ">=3.8.1"
 files = [
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+    {file = "flake8-6.1.0-py2.py3-none-any.whl", hash = "sha256:ffdfce58ea94c6580c77888a86506937f9a1a227dfcd15f245d694ae20a6b6e5"},
+    {file = "flake8-6.1.0.tar.gz", hash = "sha256:d5b3857f07c030bdb5bf41c7f53799571d75c4491748a3adcd47de929e34cd23"},
 ]
 
 [package.dependencies]
 mccabe = ">=0.7.0,<0.8.0"
-pycodestyle = ">=2.10.0,<2.11.0"
-pyflakes = ">=3.0.0,<3.1.0"
+pycodestyle = ">=2.11.0,<2.12.0"
+pyflakes = ">=3.1.0,<3.2.0"
 
 [[package]]
 name = "idna"
-version = "3.4"
+version = "3.6"
 description = "Internationalized Domain Names in Applications (IDNA)"
 optional = false
 python-versions = ">=3.5"
 files = [
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-    {file = "idna-3.4.tar.gz", hash = "sha256:814f528e8dead7d329833b91c5faa87d60bf71824cd12a7530b5526063d02cb4"},
+    {file = "idna-3.6-py3-none-any.whl", hash = "sha256:c05567e9c24a6b9faaa835c4821bad0590fbb9d5779e7caa6e1cc4978e7eb24f"},
+    {file = "idna-3.6.tar.gz", hash = "sha256:9ecdbbd083b06798ae1e86adcbfe8ab1479cf864e4ee30fe4e46a003d12491ca"},
 ]
 
 [[package]]
@@ -575,13 +582,13 @@ files = [
 
 [[package]]
 name = "importlib-metadata"
-version = "6.0.0"
+version = "6.7.0"
 description = "Read metadata from Python packages"
 optional = false
 python-versions = ">=3.7"
 files = [
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-    {file = "importlib_metadata-6.0.0.tar.gz", hash = "sha256:e354bedeb60efa6affdcc8ae121b73544a7aa74156d047311948f6d711cd378d"},
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+    {file = "importlib_metadata-6.7.0.tar.gz", hash = "sha256:1aaf550d4f73e5d6783e7acb77aec43d49da8017410afae93822cc9cca98c4d4"},
 ]
 
 [package.dependencies]
@@ -591,7 +598,7 @@ zipp = ">=0.5"
 [package.extras]
 docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
 perf = ["ipython"]
-testing = ["flake8 (<5)", "flufl.flake8", "importlib-resources (>=1.3)", "packaging", "pyfakefs", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)", "pytest-perf (>=0.9.2)"]
+testing = ["flufl.flake8", "importlib-resources (>=1.3)", "packaging", "pyfakefs", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-mypy (>=0.9.1)", "pytest-perf (>=0.9.2)", "pytest-ruff"]
 
 [[package]]
 name = "iniconfig"
@@ -617,18 +624,18 @@ files = [
 
 [[package]]
 name = "isort"
-version = "5.11.4"
+version = "5.11.5"
 description = "A Python utility / library to sort Python imports."
 optional = false
 python-versions = ">=3.7.0"
 files = [
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 ]
 
 [package.extras]
 colors = ["colorama (>=0.4.3,<0.5.0)"]
-pipfile-deprecated-finder = ["pipreqs", "requirementslib"]
+pipfile-deprecated-finder = ["pip-shims (>=0.5.2)", "pipreqs", "requirementslib"]
 plugins = ["setuptools"]
 requirements-deprecated-finder = ["pip-api", "pipreqs"]
 
@@ -651,13 +658,13 @@ i18n = ["Babel (>=2.7)"]
 
 [[package]]
 name = "jinxed"
-version = "1.2.0"
+version = "1.2.1"
 description = "Jinxed Terminal Library"
 optional = false
 python-versions = "*"
 files = [
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+    {file = "jinxed-1.2.1.tar.gz", hash = "sha256:30c3f861b73279fea1ed928cfd4dfb1f273e16cd62c8a32acfac362da0f78f3f"},
 ]
 
 [package.dependencies]
@@ -665,61 +672,71 @@ ansicon = {version = "*", markers = "platform_system == \"Windows\""}
 
 [[package]]
 name = "markupsafe"
-version = "2.1.2"
+version = "2.1.3"
 description = "Safely add untrusted strings to HTML/XML markup."
 optional = false
 python-versions = ">=3.7"
 files = [
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 [[package]]
@@ -735,24 +752,24 @@ files = [
 
 [[package]]
 name = "mypy-extensions"
-version = "0.4.3"
-description = "Experimental type system extensions for programs checked with the mypy typechecker."
+version = "1.0.0"
+description = "Type system extensions for programs checked with the mypy type checker."
 optional = false
-python-versions = "*"
+python-versions = ">=3.5"
 files = [
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 ]
 
 [[package]]
 name = "packaging"
-version = "23.0"
+version = "23.2"
 description = "Core utilities for Python packages"
 optional = false
 python-versions = ">=3.7"
 files = [
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 ]
 
 [[package]]
@@ -778,42 +795,42 @@ invoke = ["invoke (>=2.0)"]
 
 [[package]]
 name = "pathspec"
-version = "0.11.0"
+version = "0.11.2"
 description = "Utility library for gitignore style pattern matching of file paths."
 optional = false
 python-versions = ">=3.7"
 files = [
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 ]
 
 [[package]]
 name = "platformdirs"
-version = "2.6.2"
+version = "4.0.0"
 description = "A small Python package for determining appropriate platform-specific dirs, e.g. a \"user data dir\"."
 optional = false
 python-versions = ">=3.7"
 files = [
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 ]
 
 [package.dependencies]
-typing-extensions = {version = ">=4.4", markers = "python_version < \"3.8\""}
+typing-extensions = {version = ">=4.7.1", markers = "python_version < \"3.8\""}
 
 [package.extras]
-docs = ["furo (>=2022.12.7)", "proselint (>=0.13)", "sphinx (>=5.3)", "sphinx-autodoc-typehints (>=1.19.5)"]
-test = ["appdirs (==1.4.4)", "covdefaults (>=2.2.2)", "pytest (>=7.2)", "pytest-cov (>=4)", "pytest-mock (>=3.10)"]
+docs = ["furo (>=2023.7.26)", "proselint (>=0.13)", "sphinx (>=7.1.1)", "sphinx-autodoc-typehints (>=1.24)"]
+test = ["appdirs (==1.4.4)", "covdefaults (>=2.3)", "pytest (>=7.4)", "pytest-cov (>=4.1)", "pytest-mock (>=3.11.1)"]
 
 [[package]]
 name = "pluggy"
-version = "1.0.0"
+version = "1.2.0"
 description = "plugin and hook calling mechanisms for python"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 files = [
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+    {file = "pluggy-1.2.0.tar.gz", hash = "sha256:d12f0c4b579b15f5e054301bb226ee85eeeba08ffec228092f8defbaa3a4c4b3"},
 ]
 
 [package.dependencies]
@@ -825,13 +842,13 @@ testing = ["pytest", "pytest-benchmark"]
 
 [[package]]
 name = "prompt-toolkit"
-version = "3.0.36"
+version = "3.0.43"
 description = "Library for building powerful interactive command lines in Python"
 optional = false
-python-versions = ">=3.6.2"
+python-versions = ">=3.7.0"
 files = [
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+    {file = "prompt_toolkit-3.0.43-py3-none-any.whl", hash = "sha256:a11a29cb3bf0a28a387fe5122cdb649816a957cd9261dcedf8c9f1fef33eacf6"},
+    {file = "prompt_toolkit-3.0.43.tar.gz", hash = "sha256:3527b7af26106cbc65a040bcc84839a3566ec1b051bb0bfe953631e704b0ff7d"},
 ]
 
 [package.dependencies]
@@ -839,13 +856,13 @@ wcwidth = "*"
 
 [[package]]
 name = "pycodestyle"
-version = "2.10.0"
+version = "2.11.1"
 description = "Python style guide checker"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
 files = [
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 ]
 
 [[package]]
@@ -861,28 +878,29 @@ files = [
 
 [[package]]
 name = "pyflakes"
-version = "3.0.1"
+version = "3.1.0"
 description = "passive checker of Python programs"
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.8"
 files = [
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 ]
 
 [[package]]
 name = "pygments"
-version = "2.14.0"
+version = "2.17.2"
 description = "Pygments is a syntax highlighting package written in Python."
 optional = false
-python-versions = ">=3.6"
+python-versions = ">=3.7"
 files = [
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 ]
 
 [package.extras]
 plugins = ["importlib-metadata"]
+windows-terminal = ["colorama (>=0.4.6)"]
 
 [[package]]
 name = "pynacl"
@@ -912,17 +930,16 @@ tests = ["hypothesis (>=3.27.0)", "pytest (>=3.2.1,!=3.3.0)"]
 
 [[package]]
 name = "pytest"
-version = "7.2.1"
+version = "7.4.3"
 description = "pytest: simple powerful testing with Python"
 optional = false
 python-versions = ">=3.7"
 files = [
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 exceptiongroup = {version = ">=1.0.0rc8", markers = "python_version < \"3.11\""}
 importlib-metadata = {version = ">=0.12", markers = "python_version < \"3.8\""}
@@ -932,7 +949,7 @@ pluggy = ">=0.12,<2.0"
 tomli = {version = ">=1.0.0", markers = "python_version < \"3.11\""}
 
 [package.extras]
-testing = ["argcomplete", "hypothesis (>=3.56)", "mock", "nose", "pygments (>=2.7.2)", "requests", "xmlschema"]
+testing = ["argcomplete", "attrs (>=19.2.0)", "hypothesis (>=3.56)", "mock", "nose", "pygments (>=2.7.2)", "requests", "setuptools", "xmlschema"]
 
 [[package]]
 name = "pytest-cov"
@@ -985,13 +1002,13 @@ dev = ["pre-commit", "pytest-asyncio", "tox"]
 
 [[package]]
 name = "pytest-regressions"
-version = "2.4.2"
+version = "2.4.3"
 description = "Easy to use fixtures to write regression tests."
 optional = false
 python-versions = ">=3.6"
 files = [
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 ]
 
 [package.dependencies]
@@ -1019,64 +1036,88 @@ files = [
 [package.dependencies]
 pytest = ">=3.6.3"
 
+[[package]]
+name = "pytest-timeout"
+version = "2.2.0"
+description = "pytest plugin to abort hanging tests"
+optional = false
+python-versions = ">=3.7"
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+]
+
+[package.dependencies]
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+
 [[package]]
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+version = "2023.3.post1"
 description = "World timezone definitions, modern and historical"
 optional = false
 python-versions = "*"
 files = [
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 [[package]]
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 charset-normalizer = ">=2,<4"
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 [package.extras]
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+sphinxcontrib-jquery = ">=4,<5"
 
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 test = ["html5lib", "pytest"]
 
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+optional = false
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 version = "1.0.1"
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+    {file = "wrapt-1.16.0.tar.gz", hash = "sha256:5f370f952971e7d17c7d1ead40e49f32345a7f7a5373571ef44d800d06b1899d"},
 ]
 
 [[package]]
 name = "zipp"
-version = "3.11.0"
+version = "3.15.0"
 description = "Backport of pathlib-compatible object wrapper for zip files"
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "zipp-3.11.0-py3-none-any.whl", hash = "sha256:83a28fcb75844b5c0cdaf5aa4003c2d728c77e05f5aeabe8e95e56727005fbaa"},
-    {file = "zipp-3.11.0.tar.gz", hash = "sha256:a7a22e05929290a67401440b39690ae6563279bced5f314609d9d03798f56766"},
+    {file = "zipp-3.15.0-py3-none-any.whl", hash = "sha256:48904fc76a60e542af151aded95726c1a5c34ed43ab4134b597665c86d7ad556"},
+    {file = "zipp-3.15.0.tar.gz", hash = "sha256:112929ad649da941c23de50f356a2b5570c954b65150642bccdd66bf194d224b"},
 ]
 
 [package.extras]
-docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)"]
-testing = ["flake8 (<5)", "func-timeout", "jaraco.functools", "jaraco.itertools", "more-itertools", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)"]
+docs = ["furo", "jaraco.packaging (>=9)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
+testing = ["big-O", "flake8 (<5)", "jaraco.functools", "jaraco.itertools", "more-itertools", "pytest (>=6)", "pytest-black (>=0.3.7)", "pytest-checkdocs (>=2.4)", "pytest-cov", "pytest-enabler (>=1.3)", "pytest-flake8", "pytest-mypy (>=0.9.1)"]
 
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.7"
-content-hash = "6a7c6ae677b3a04605131d53031df9036571bb5ebbd87d166445fb7263bcf275"
+content-hash = "79a2e67c2001f854824d8c49a2a47d23e97890009a19f361df5d9deba1f6b728"
diff --git a/pyproject.toml b/pyproject.toml
index 970161f4..f7f61492 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -38,6 +38,10 @@ pytest-mock = "^3.11.1"
 pytest-socket = "^0.6.0"
 pytest-cov = "^4.1.0"
 
+
+[tool.poetry.group.test.dependencies]
+pytest-timeout = "^2.1.0"
+
 [tool.isort]
 multi_line_output = 3
 include_trailing_comma = true
diff --git a/tests/cli/common.py b/tests/cli/common.py
index afa623f5..de8eb31d 100644
--- a/tests/cli/common.py
+++ b/tests/cli/common.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 
+import functools
 import inspect
 import os
 import sys
@@ -7,6 +8,8 @@
 from subprocess import CompletedProcess
 from typing import Any, Callable
 
+import fabric
+import paramiko.ssh_exception
 import pytest
 from pytest_regressions.file_regression import FileRegressionFixture
 from typing_extensions import ParamSpec
@@ -14,8 +17,34 @@
 if typing.TYPE_CHECKING:
     from typing_extensions import TypeGuard
 
+in_github_CI = all(var in os.environ for var in ["CI", "GITHUB_ACTION", "GITHUB_ENV"])
+"""True if this is being run inside the GitHub CI."""
+
+skip_if_on_github_CI = pytest.mark.skipif(
+    in_github_CI, reason="This test shouldn't run on the Github CI."
+)
+skip_param_if_on_github_ci = functools.partial(pytest.param, marks=skip_if_on_github_CI)
+
+
+passwordless_ssh_connection_to_localhost_is_setup = False
+
+try:
+    _connection = fabric.Connection("localhost")
+    _connection.open()
+except (
+    paramiko.ssh_exception.SSHException,
+    paramiko.ssh_exception.NoValidConnectionsError,
+):
+    pass
+else:
+    passwordless_ssh_connection_to_localhost_is_setup = True
+    _connection.close()
+
+requires_ssh_to_localhost = pytest.mark.skipif(
+    not passwordless_ssh_connection_to_localhost_is_setup,
+    reason="Test requires a SSH connection to localhost.",
+)
 
-P = ParamSpec("P")
 
 REQUIRES_S_FLAG_REASON = (
     "Seems to require reading from stdin? Works with the -s flag, but other "
@@ -32,7 +61,9 @@
     reason="Passing pytest's -s flag makes this test fail.",
 )
 on_windows = sys.platform == "win32"
-in_github_windows_ci = os.environ.get("PLATFORM") == "windows-latest"
+in_github_windows_ci = in_github_CI and os.environ.get("PLATFORM") == "windows-latest"
+
+P = ParamSpec("P")
 
 
 def xfails_on_windows(
diff --git a/tests/cli/test_commands.py b/tests/cli/test_commands.py
index 1418fdb0..3b35c085 100644
--- a/tests/cli/test_commands.py
+++ b/tests/cli/test_commands.py
@@ -1,19 +1,11 @@
 import contextlib
-import importlib
 import io
 import shlex
-import subprocess
-from subprocess import CompletedProcess
-from unittest import mock
 
 import pytest
-from fabric.testing.fixtures import Connection, MockRemote, remote  # noqa
-from pytest_mock import MockerFixture
 from pytest_regressions.file_regression import FileRegressionFixture
-from typing_extensions import ParamSpec
 
 from milatools.cli.commands import main
-from milatools.cli.local import Local
 
 from .common import requires_no_s_flag
 
@@ -23,51 +15,6 @@ def _convert_argparse_output_to_pre_py311_format(output: str) -> str:
     return output.replace("options:\n", "optional arguments:\n")
 
 
-P = ParamSpec("P")
-
-
-def reload_module():
-    """Reload the module after mocking out functions.
-
-    Need to reload the module because we have mocked some of the functions that are used
-    as default values in the methods of the class under test (e.g. `subprocess.run`).
-    The functions being in the signature of the methods makes it possible for us to
-    describe their our method signatures explicitly, but it means that we need to reload
-    the module after mocking them.
-    """
-    global Local
-    import milatools.cli.local
-
-    importlib.reload(milatools.cli.local)
-    Local = milatools.cli.local.Local
-
-
-@pytest.fixture
-def mock_subprocess_run(mocker: MockerFixture) -> mock.Mock:
-    mock_subprocess_run: mock.Mock = mocker.patch("subprocess.run")
-    # NOTE: Trying out https://stackoverflow.com/questions/25692440/mocking-a-subprocess-call-in-python
-
-    reload_module()
-    return mock_subprocess_run
-
-
-def test_check_passwordless(
-    mock_subprocess_run: mock.Mock,
-):
-    # NOTE: Trying out https://stackoverflow.com/questions/25692440/mocking-a-subprocess-call-in-python
-    mock_subprocess_run.return_value = CompletedProcess(["echo OK"], 0, stdout="BOBOBO")
-    local = Local()
-    local.check_passwordless("mila")
-
-    mock_subprocess_run.assert_called_once_with(
-        tuple(shlex.split("ssh -oPreferredAuthentications=publickey mila 'echo OK'")),
-        stdout=subprocess.PIPE,
-        stderr=subprocess.PIPE,
-        capture_output=False,
-        universal_newlines=True,
-    )
-
-
 @requires_no_s_flag
 @pytest.mark.parametrize(
     "command",
diff --git a/tests/cli/test_init_command.py b/tests/cli/test_init_command.py
index def41b93..2df23f6f 100644
--- a/tests/cli/test_init_command.py
+++ b/tests/cli/test_init_command.py
@@ -2,31 +2,47 @@
 
 import contextlib
 import json
+import os
+import shutil
 import subprocess
 import sys
 import textwrap
 from functools import partial
+from logging import getLogger as get_logger
 from pathlib import Path
 from unittest.mock import Mock
 
 import pytest
+import pytest_mock
 import questionary
 from prompt_toolkit.input import PipeInput, create_pipe_input
 from pytest_regressions.file_regression import FileRegressionFixture
 
 from milatools.cli import init_command
 from milatools.cli.init_command import (
-    _get_username,
+    DRAC_CLUSTERS,
+    _get_drac_username,
+    _get_mila_username,
     _setup_ssh_config_file,
     create_ssh_keypair,
     get_windows_home_path_in_wsl,
+    setup_passwordless_ssh_access,
+    setup_passwordless_ssh_access_to_cluster,
     setup_ssh_config,
     setup_vscode_settings,
     setup_windows_ssh_config_from_wsl,
 )
-from milatools.cli.local import Local
+from milatools.cli.local import Local, check_passwordless
 from milatools.cli.utils import SSHConfig, running_inside_WSL
-from tests.cli.common import xfails_on_windows
+
+from .common import (
+    in_github_CI,
+    on_windows,
+    passwordless_ssh_connection_to_localhost_is_setup,
+    xfails_on_windows,
+)
+
+logger = get_logger(__name__)
 
 
 def raises_NoConsoleScreenBufferError_on_windows_ci_action():
@@ -52,6 +68,10 @@ def permission_bits_check_doesnt_work_on_windows():
     )
 
 
+# Set a module-level mark: Each test cannot take longer than 1 second to run.
+pytestmark = pytest.mark.timeout(10)
+
+
 @pytest.fixture
 def input_pipe(monkeypatch: pytest.MonkeyPatch, request: pytest.FixtureRequest):
     """Fixture that creates an input pipe and makes questionary use it.
@@ -102,12 +122,27 @@ def _yn(accept: bool):
 def test_creates_ssh_config_file(tmp_path: Path, input_pipe: PipeInput):
     ssh_config_path = tmp_path / "ssh_config"
 
-    for prompt in ["y", "bob\r", "y", "y", "y", "y", "y"]:
+    for prompt in [
+        "y",
+        "bob\r",  # mila username
+        "y",  # drac?
+        "bob\r",  # drac username
+        "y",
+        "y",
+        "y",
+        "y",
+        "y",
+    ]:
         input_pipe.send_text(prompt)
     setup_ssh_config(tmp_path / "ssh_config")
     assert ssh_config_path.exists()
 
 
+@pytest.mark.parametrize(
+    "drac_username",
+    [None, "bob"],
+    ids=["no_drac", "drac"],
+)
 @pytest.mark.parametrize(
     "confirm_changes",
     [False, True],
@@ -155,6 +190,7 @@ def test_creates_ssh_config_file(tmp_path: Path, input_pipe: PipeInput):
 def test_setup_ssh(
     initial_contents: str,
     confirm_changes: bool,
+    drac_username: str | None,
     tmp_path: Path,
     file_regression: FileRegressionFixture,
     input_pipe: PipeInput,
@@ -172,7 +208,10 @@ def test_setup_ssh(
             f.write(initial_contents)
 
     user_inputs = [
-        "bob\r",  # username
+        "bob\r",  # username on Mila cluster
+        *(  # DRAC account? + enter username
+            ["n"] if drac_username is None else ["y", drac_username + "\r"]
+        ),
         _yn(confirm_changes),
     ]
     for prompt in user_inputs:
@@ -235,7 +274,12 @@ def test_fixes_overly_general_entry(
         f.write(initial_contents)
 
     # Enter username, accept fixing that entry, then confirm.
-    for user_input in ["bob\r", "y", "y"]:
+    for user_input in [
+        "bob\r",  # mila username
+        "n",  # DRAC account?
+        "y",
+        "y",
+    ]:
         input_pipe.send_text(user_input)
 
     setup_ssh_config(ssh_config_path=ssh_config_path)
@@ -278,6 +322,9 @@ def test_ssh_config_host(tmp_path: Path):
     }
 
 
+@pytest.mark.parametrize(
+    "already_has_drac", [True, False], ids=["has_drac_entries", "no_drac_entries"]
+)
 @pytest.mark.parametrize(
     "already_has_mila", [True, False], ids=["has_mila_entry", "no_mila_entry"]
 )
@@ -295,15 +342,17 @@ def test_with_existing_entries(
     already_has_mila: bool,
     already_has_mila_cpu: bool,
     already_has_mila_compute: bool,
+    already_has_drac: bool,
     file_regression: FileRegressionFixture,
     tmp_path: Path,
     input_pipe: PipeInput,
 ):
+    user = "bob"
     existing_mila = textwrap.dedent(
-        """\
+        f"""\
         Host mila
           HostName login.server.mila.quebec
-          User bob
+          User {user}
         """
     )
     existing_mila_cpu = textwrap.dedent(
@@ -318,11 +367,38 @@ def test_with_existing_entries(
           HostName foooobar.com
         """
     )
+    existing_drac = textwrap.dedent(
+        f"""
+        # Compute Canada
+        Host beluga cedar graham narval niagara
+          Hostname %h.alliancecan.ca
+          User {user}
+        Host mist
+          Hostname mist.scinet.utoronto.ca
+          User {user}
+        Host !beluga  bc????? bg????? bl?????
+          ProxyJump beluga
+          User {user}
+        Host !cedar   cdr? cdr?? cdr??? cdr????
+          ProxyJump cedar
+          User {user}
+        Host !graham  gra??? gra????
+          ProxyJump graham
+          User {user}
+        Host !narval  nc????? ng?????
+          ProxyJump narval
+          User {user}
+        Host !niagara nia????
+          ProxyJump niagara
+          User {user}
+        """
+    )
 
     initial_blocks = []
     initial_blocks += [existing_mila] if already_has_mila else []
     initial_blocks += [existing_mila_cpu] if already_has_mila_cpu else []
     initial_blocks += [existing_mila_compute] if already_has_mila_compute else []
+    initial_blocks += [existing_drac] if already_has_drac else []
     initial_contents = _join_blocks(*initial_blocks)
 
     # TODO: Need to insert the entries in the right place, in the right order!
@@ -346,11 +422,13 @@ def test_with_existing_entries(
             "  ControlPersist 600",
         ]
     )
+
     if not all(
         [
             already_has_mila and controlmaster_block in existing_mila,
             already_has_mila_cpu,
             already_has_mila_compute and controlmaster_block in existing_mila_compute,
+            already_has_drac,
         ]
     ):
         # There's a confirmation prompt only if we're adding some entry.
@@ -358,7 +436,10 @@ def test_with_existing_entries(
     else:
         confirm_inputs = []
 
-    prompt_inputs = username_input + confirm_inputs
+    drac_username_inputs = []
+    if not already_has_drac:
+        drac_username_inputs = ["y", f"{user}\r"]
+    prompt_inputs = username_input + drac_username_inputs + confirm_inputs
 
     for prompt_input in prompt_inputs:
         input_pipe.send_text(prompt_input)
@@ -484,7 +565,103 @@ def test_get_username(
         input_pipe.close()
     for prompt_input in prompt_inputs:
         input_pipe.send_text(prompt_input)
-    assert _get_username(ssh_config) == expected
+    assert _get_mila_username(ssh_config) == expected
+
+
+@pytest.mark.parametrize(
+    ("contents", "prompt_inputs", "expected"),
+    [
+        pytest.param(
+            "",  # empty file.
+            ["n"],  # No I don't have a DRAC account.
+            None,  # get None as a result
+            id="no_drac_account",
+        ),
+        pytest.param(
+            "",  # empty file.
+            ["y", "bob\r"],  # enter yes, then "bob" then enter.
+            "bob",  # get "bob" as username.
+            id="empty_file",
+        ),
+        pytest.param(
+            textwrap.dedent(
+                """\
+                Host narval
+                  HostName narval.computecanada.ca
+                  User bob
+                """
+            ),
+            [],
+            "bob",
+            id="existing_drac_entry",
+        ),
+        pytest.param(
+            textwrap.dedent(
+                """\
+                Host beluga cedar graham narval niagara
+                  HostName %h.computecanada.ca
+                  ControlMaster auto
+                  ControlPath ~/.cache/ssh/%r@%h:%p
+                  ControlPersist 600
+                """
+            ),
+            ["y", "bob\r"],  # Yes I have a username on the drac clusters, and it's bob.
+            "bob",
+            id="entry_without_user",
+        ),
+        pytest.param(
+            textwrap.dedent(
+                """\
+                Host beluga cedar graham narval niagara
+                    HostName login.server.mila.quebec
+                    User george
+                # duplicate entry
+                Host beluga cedar graham narval niagara other_cluster
+                    User Bob
+                """
+            ),
+            ["y", "bob\r"],
+            "bob",
+            id="two_matching_entries",
+        ),
+        pytest.param(
+            textwrap.dedent(
+                """\
+                Host fooo beluga bar baz
+                    HostName beluga.alliancecan.ca
+                    User george
+                """
+            ),
+            [],
+            "george",
+            id="with_aliases",
+        ),
+        pytest.param(
+            "",
+            # Yes (by pressing just enter), then an invalid username (space), then a
+            # real username.
+            ["\r", " \r", "bob\r"],
+            "bob",
+            id="empty_username",
+        ),
+    ],
+)
+def test_get_drac_username(
+    contents: str,
+    prompt_inputs: list[str],
+    expected: str | None,
+    input_pipe: PipeInput,
+    tmp_path: Path,
+):
+    ssh_config_path = tmp_path / "config"
+    with open(ssh_config_path, "w") as f:
+        f.write(contents)
+    ssh_config = SSHConfig(ssh_config_path)
+    if not prompt_inputs:
+        input_pipe.close()
+    for prompt_input in prompt_inputs:
+        input_pipe.send_text(prompt_input)
+    assert _get_drac_username(ssh_config) == expected
 
 
 class TestSetupSshFile:
@@ -549,7 +726,8 @@ def test_fixes_dir_permission_issues(
         assert file.stat().st_mode & 0o777 == 0o600
 
 
-@permission_bits_check_doesnt_work_on_windows()
+# takes a little longer in the CI runner (Windows in particular)
+@pytest.mark.timeout(10)
 def test_create_ssh_keypair(monkeypatch: pytest.MonkeyPatch, tmp_path: Path):
     here = Local()
     mock_run = Mock(
@@ -559,19 +737,17 @@ def test_create_ssh_keypair(monkeypatch: pytest.MonkeyPatch, tmp_path: Path):
     fake_ssh_folder = tmp_path / "fake_ssh"
     fake_ssh_folder.mkdir(mode=0o700)
     ssh_private_key_path = fake_ssh_folder / "bob"
+
     create_ssh_keypair(ssh_private_key_path=ssh_private_key_path, local=here)
-    mock_run.assert_called_once_with(
-        ("ssh-keygen", "-f", str(ssh_private_key_path), "-t", "rsa", "-N=''"),
-        universal_newlines=True,
-        capture_output=False,
-        stderr=None,
-        stdout=None,
-    )
+
+    mock_run.assert_called_once()
     assert ssh_private_key_path.exists()
-    assert ssh_private_key_path.stat().st_mode & 0o777 == 0o600
+    if not on_windows:
+        assert ssh_private_key_path.stat().st_mode & 0o777 == 0o600
     ssh_public_key_path = ssh_private_key_path.with_suffix(".pub")
     assert ssh_public_key_path.exists()
-    assert ssh_public_key_path.stat().st_mode & 0o777 == 0o644
+    if not on_windows:
+        assert ssh_public_key_path.stat().st_mode & 0o777 == 0o644
 
 
 @pytest.fixture
@@ -582,7 +758,13 @@ def linux_ssh_config(
     # Enter username, accept fixing that entry, then confirm.
     ssh_config_path = tmp_path / "ssh_config"
 
-    for prompt in ["y", "bob\r", "y"]:
+    for prompt in [
+        "y",  # Create an ssh config file?
+        "bob\r",  # What's your username on the Mila cluster?
+        "y",  # Do you also have a DRAC account?
+        "bob\r",  # username on DRAC
+        "y",  # accept adding the entries in the ssh config
+    ]:
         input_pipe.send_text(prompt)
 
     if sys.platform.startswith("win"):
@@ -803,3 +985,270 @@ def test_setup_windows_ssh_config_from_wsl_copies_keys(
     assert windows_private_key_path.read_text() == private_key_text
     assert windows_public_key_path.exists()
     assert windows_public_key_path.read_text() == public_key_text
+
+
+BACKUP_SSH_DIR = Path.home() / ".ssh_backup"
+USE_MY_REAL_SSH_DIR = os.environ.get("USE_MY_REAL_SSH_DIR", "0") == "1"
+"""Set this to `True` for the tests below to actually use your real SSH directory.
+
+A backup is saved in `BACKUP_SSH_DIR`.
+"""
+
+
+@pytest.fixture
+def backup_ssh_dir():
+    """Creates a backup of the SSH config files."""
+    import shutil
+
+    assert in_github_CI or USE_MY_REAL_SSH_DIR
+
+    ssh_dir = Path.home() / ".ssh"
+    backup_ssh_dir = BACKUP_SSH_DIR
+
+    ssh_dir_existed_before = ssh_dir.exists()
+
+    def _ignore_sockets_dir(src: str, names: list[str]) -> list[str]:
+        return names if Path(src).name == "sockets" else []
+
+    if ssh_dir_existed_before:
+        logger.warning(f"Backing up {ssh_dir} to {backup_ssh_dir}")
+        if backup_ssh_dir.exists():
+            shutil.rmtree(backup_ssh_dir)
+        shutil.copytree(ssh_dir, backup_ssh_dir, ignore=_ignore_sockets_dir)
+    else:
+        logger.warning(f"Test might temporarily create files in a new {ssh_dir} dir.")
+
+    yield backup_ssh_dir
+
+    if ssh_dir_existed_before:
+        logger.warning(f"Restoring {ssh_dir} from backup at {backup_ssh_dir}")
+        if ssh_dir.exists():
+            shutil.rmtree(ssh_dir)
+        shutil.copytree(backup_ssh_dir, ssh_dir)
+        shutil.rmtree(backup_ssh_dir)
+    else:
+        logger.warning(f"Removing temporarily generated sshdir at {ssh_dir}.")
+        if ssh_dir.exists():
+            shutil.rmtree(ssh_dir)
+
+
+@pytest.mark.skipif(
+    not (
+        (in_github_CI or USE_MY_REAL_SSH_DIR)
+        and passwordless_ssh_connection_to_localhost_is_setup
+    ),
+    reason=(
+        "It's a bit risky to actually change the SSH config directory on a dev "
+        "machine. Only doing it in the CI or if the USE_MY_REAL_SSH_DIR env var is set."
+    ),
+)
+@pytest.mark.timeout(20)
+@pytest.mark.parametrize(
+    "passwordless_to_cluster_is_already_setup",
+    [True, False],
+    ids=["already_setup", "not_already_setup"],
+)
+@pytest.mark.parametrize(
+    "user_accepts_registering_key",
+    [True, False],
+    ids=["accept_registering_key", "reject_registering_key"],
+)
+def test_setup_passwordless_ssh_access_to_cluster(
+    input_pipe: PipeInput,
+    backup_ssh_dir: Path,
+    mocker: pytest_mock.MockerFixture,
+    passwordless_to_cluster_is_already_setup: bool,
+    user_accepts_registering_key: bool,
+):
+    """Test the function that sets up passwordless SSH to a cluster (localhost in tests)
+
+    NOTE: Running this test will make a backup of the ~/.ssh directory in
+    `backup_ssh_dir` (~/.ssh_backup), and restore it after the test.
+    For that reason, it currently only runs in the GitHub CI, unless you specifically
+    set the `USE_MY_REAL_SSH_DIR` env variable to '1'.
+    """
+    assert passwordless_ssh_connection_to_localhost_is_setup
+    assert in_github_CI or USE_MY_REAL_SSH_DIR
+
+    ssh_dir = Path.home() / ".ssh"
+    authorized_keys_file = ssh_dir / "authorized_keys"
+    backup_authorized_keys_file = backup_ssh_dir / "authorized_keys"
+    assert backup_authorized_keys_file.exists()
+
+    if not passwordless_to_cluster_is_already_setup:
+        if authorized_keys_file.exists():
+            logger.warning(
+                f"Temporarily removing {authorized_keys_file}. "
+                f"(A backup is available at {backup_authorized_keys_file})"
+            )
+            authorized_keys_file.unlink()
+
+        input_pipe.send_text("y" if user_accepts_registering_key else "n")
+
+        assert not check_passwordless("localhost")
+    else:
+        assert check_passwordless("localhost")
+
+    logger.info(backup_authorized_keys_file.read_text())
+
+    def _mock_subprocess_run(command: tuple[str], *args, **kwargs):
+        """Mock of the ssh-copy-id command.
+
+        Copies the `authorized_keys` file from the backup to the (temporarily cleared)
+        .ssh directory.
+        """
+        logger.debug(f"Running: {command} {args} {kwargs}")
+        if sys.platform == "linux":
+            assert command[0] == "ssh-copy-id"
+        ssh_dir.mkdir(exist_ok=True, mode=0o700)
+        shutil.copy(backup_authorized_keys_file, authorized_keys_file)
+        return subprocess.CompletedProcess(command, 0, "", "")
+
+    mock_subprocess_run = mocker.patch("subprocess.run", wraps=_mock_subprocess_run)
+
+    success = setup_passwordless_ssh_access_to_cluster("localhost")
+
+    if passwordless_to_cluster_is_already_setup:
+        mock_subprocess_run.assert_not_called()
+        assert success is True
+    elif user_accepts_registering_key:
+        mock_subprocess_run.assert_called_once()
+        assert success is True
+    else:
+        mock_subprocess_run.assert_not_called()
+        assert success is False
+
+
+@pytest.mark.timeout(10)
+@pytest.mark.skipif(
+    not (in_github_CI or USE_MY_REAL_SSH_DIR),
+    reason=(
+        "It's a bit risky to actually change the SSH config directory on a dev "
+        "machine. Only doing it in the CI or if the USE_MY_REAL_SSH_DIR env var is set."
+    ),
+)
+@pytest.mark.parametrize(
+    "drac_clusters_in_ssh_config",
+    [[]] + [DRAC_CLUSTERS[i:] for i in range(len(DRAC_CLUSTERS))],
+)
+@pytest.mark.parametrize(
+    "accept_generating_key",
+    [True, False],
+    ids=["accept_generate_key", "accept_generate_key"],
+)
+@pytest.mark.parametrize(
+    "public_key_exists",
+    [True, False],
+    ids=["key_exists", "no_key"],
+)
+@pytest.mark.parametrize(
+    "accept_mila", [True, False], ids=["accept_mila", "reject_mila"]
+)
+@pytest.mark.parametrize(
+    "accept_drac", [True, False], ids=["accept_drac", "reject_drac"]
+)
+def test_setup_passwordless_ssh_access(
+    accept_generating_key: bool,
+    public_key_exists: bool,
+    accept_mila: bool,
+    accept_drac: bool,
+    drac_clusters_in_ssh_config: list[str],
+    # capsys: pytest.CaptureFixture,
+    monkeypatch: pytest.MonkeyPatch,
+    tmp_path: Path,
+    backup_ssh_dir: Path,
+    input_pipe: PipeInput,
+):
+    assert in_github_CI or USE_MY_REAL_SSH_DIR
+    ssh_dir = Path.home() / ".ssh"
+    if ssh_dir.exists():
+        logger.warning(
+            f"Temporarily deleting the ssh dir (backed up at {backup_ssh_dir})"
+        )
+        shutil.rmtree(ssh_dir)
+
+    if not public_key_exists:
+        # There should be no ssh keys in the ssh dir before calling the function.
+        # We should get a prompt asking if we want to generate a key.
+        input_pipe.send_text("y" if accept_generating_key else "n")
+    else:
+        # There should be an ssh key in the .ssh dir.
+        # Won't ask to generate a key.
+        create_ssh_keypair(
+            ssh_private_key_path=ssh_dir / "id_rsa_milatools", local=Local()
+        )
+        if drac_clusters_in_ssh_config:
+            # We should get a promtp asking if we want or not to register the public key
+            # on the DRAC clusters.
+            input_pipe.send_text("y" if accept_drac else "n")
+
+    # Pre-populate the ssh config file.
+    ssh_config_path = tmp_path / "ssh_config"
+    ssh_config_path.write_text(
+        textwrap.dedent(
+            f"""\
+            Host {' '.join(drac_clusters_in_ssh_config)}
+                Hostname %h.computecanada.ca
+                User bob
+            """
+        )
+        if drac_clusters_in_ssh_config
+        else ""
+    )
+    ssh_config = SSHConfig(path=ssh_config_path)
+
+    # We mock the main function used by the `setup_passwordless_ssh_access` function.
+    # It's okay because we have a good test for it above. Therefore we just test how it
+    # gets called here.
+    mock_setup_passwordless_ssh_access_to_cluster = Mock(
+        spec=setup_passwordless_ssh_access_to_cluster,
+        side_effect=[accept_mila, *(accept_drac for _ in drac_clusters_in_ssh_config)],
+    )
+    import milatools.cli.init_command
+
+    monkeypatch.setattr(
+        milatools.cli.init_command,
+        setup_passwordless_ssh_access_to_cluster.__name__,
+        mock_setup_passwordless_ssh_access_to_cluster,
+    )
+
+    result = setup_passwordless_ssh_access(ssh_config)
+
+    if not public_key_exists:
+        if accept_generating_key:
+            assert ssh_dir.exists()
+            assert ssh_dir.stat().st_mode & 0o777 == 0o700
+            assert (ssh_dir / "id_rsa").exists()
+            assert (ssh_dir / "id_rsa").stat().st_mode & 0o777 == 0o600
+            assert (ssh_dir / "id_rsa.pub").exists()
+        else:
+            assert not (ssh_dir / "id_rsa").exists()
+            assert not (ssh_dir / "id_rsa.pub").exists()
+            assert not result
+            mock_setup_passwordless_ssh_access_to_cluster.assert_not_called()
+            return
+
+    mock_setup_passwordless_ssh_access_to_cluster.assert_any_call("mila")
+    if not accept_mila:
+        mock_setup_passwordless_ssh_access_to_cluster.assert_called_once_with("mila")
+        assert result is False
+        return
+
+    # If we accept to setup passwordless SSH access to the Mila cluster, we go on
+    # to ask for DRAC clusters.
+    if not drac_clusters_in_ssh_config:
+        assert result is True
+        mock_setup_passwordless_ssh_access_to_cluster.assert_called_once_with("mila")
+        return
+
+    # If there were DRAC clusters in the SSH config, then the fn is called for each
+    # cluster, unless the user rejects setting up passwordless SSH access to one of the
+    # clusters, in which case there's an early return False.
+    if not accept_drac:
+        assert len(mock_setup_passwordless_ssh_access_to_cluster.mock_calls) == 2
+        assert result is False
+        return
+
+    for drac_cluster in drac_clusters_in_ssh_config:
+        mock_setup_passwordless_ssh_access_to_cluster.assert_any_call(drac_cluster)
+    assert result is True
diff --git a/tests/cli/test_init_command/test_fixes_overly_general_entry.txt b/tests/cli/test_init_command/test_fixes_overly_general_entry.txt
index 484af2d5..4f565d16 100644
--- a/tests/cli/test_init_command/test_fixes_overly_general_entry.txt
+++ b/tests/cli/test_init_command/test_fixes_overly_general_entry.txt
@@ -1,9 +1,6 @@
-Host *.server.mila.quebec !*login.server.mila.quebec
-  User bob
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -11,9 +8,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -23,4 +20,13 @@ Host mila-cpu
   ConnectTimeout 600
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
-  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
\ No newline at end of file
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_drac_.md
new file mode 100644
index 00000000..a4619edd
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_drac_.md
@@ -0,0 +1,66 @@
+Running the `mila init` command with no initial ssh config file
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'y')
+leads the following ssh config file:
+
+```
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_.md b/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_no_drac_.md
similarity index 92%
rename from tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_no_drac_.md
index ee5e220a..9ecbdaf1 100644
--- a/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_empty_confirm_changes_no_drac_.md
@@ -1,13 +1,12 @@
 Running the `mila init` command with no initial ssh config file
 
-and these user inputs: ('bob\r', 'y')
+and these user inputs: ('bob\r', 'n', 'y')
 leads the following ssh config file:
 
 ```
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -15,9 +14,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -28,14 +27,13 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_drac_.md
new file mode 100644
index 00000000..dc3ada1c
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_drac_.md
@@ -0,0 +1,8 @@
+Running the `mila init` command with no initial ssh config file
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'n')
+leads the following ssh config file:
+
+```
+
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_.md b/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_no_drac_.md
similarity index 72%
rename from tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_no_drac_.md
index cb6aeede..06596331 100644
--- a/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_empty_reject_changes_no_drac_.md
@@ -1,6 +1,6 @@
 Running the `mila init` command with no initial ssh config file
 
-and these user inputs: ('bob\r', 'n')
+and these user inputs: ('bob\r', 'n', 'n')
 leads the following ssh config file:
 
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md
new file mode 100644
index 00000000..b2593767
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_drac_.md
@@ -0,0 +1,80 @@
+Running the `mila init` command with this initial content:
+
+```
+# a comment
+Host foo
+  HostName foobar.com
+
+# another comment
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'y')
+leads the following ssh config file:
+
+```
+# a comment
+Host foo
+  HostName foobar.com
+
+# another comment
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md
similarity index 93%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md
index dcb3db48..b89c1401 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_confirm_changes_no_drac_.md
@@ -9,7 +9,7 @@ Host foo
 
 ```
 
-and these user inputs: ('bob\r', 'y')
+and these user inputs: ('bob\r', 'n', 'y')
 leads the following ssh config file:
 
 ```
@@ -21,7 +21,6 @@ Host foo
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -29,9 +28,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -42,14 +41,13 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md
new file mode 100644
index 00000000..44334113
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_drac_.md
@@ -0,0 +1,22 @@
+Running the `mila init` command with this initial content:
+
+```
+# a comment
+Host foo
+  HostName foobar.com
+
+# another comment
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'n')
+leads the following ssh config file:
+
+```
+# a comment
+Host foo
+  HostName foobar.com
+
+# another comment
+
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md
similarity index 84%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md
index 1ba16f4f..4db55afd 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_reject_changes_no_drac_.md
@@ -9,7 +9,7 @@ Host foo
 
 ```
 
-and these user inputs: ('bob\r', 'n')
+and these user inputs: ('bob\r', 'n', 'n')
 leads the following ssh config file:
 
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md
new file mode 100644
index 00000000..594f817d
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_drac_.md
@@ -0,0 +1,88 @@
+Running the `mila init` command with this initial content:
+
+```
+# a comment
+
+Host foo
+  HostName foobar.com
+
+
+
+
+# another comment after lots of empty lines.
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'y')
+leads the following ssh config file:
+
+```
+# a comment
+
+Host foo
+  HostName foobar.com
+
+
+
+
+# another comment after lots of empty lines.
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md
similarity index 93%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md
index c75603fa..ce4cf361 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_confirm_changes_no_drac_.md
@@ -13,7 +13,7 @@ Host foo
 
 ```
 
-and these user inputs: ('bob\r', 'y')
+and these user inputs: ('bob\r', 'n', 'y')
 leads the following ssh config file:
 
 ```
@@ -29,7 +29,6 @@ Host foo
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -37,9 +36,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -50,14 +49,13 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md
new file mode 100644
index 00000000..2239f984
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_drac_.md
@@ -0,0 +1,30 @@
+Running the `mila init` command with this initial content:
+
+```
+# a comment
+
+Host foo
+  HostName foobar.com
+
+
+
+
+# another comment after lots of empty lines.
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'n')
+leads the following ssh config file:
+
+```
+# a comment
+
+Host foo
+  HostName foobar.com
+
+
+
+
+# another comment after lots of empty lines.
+
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md
similarity index 87%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md
index 1436b7b2..3b82c33d 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_and_entry_with_extra_space_reject_changes_no_drac_.md
@@ -13,7 +13,7 @@ Host foo
 
 ```
 
-and these user inputs: ('bob\r', 'n')
+and these user inputs: ('bob\r', 'n', 'n')
 leads the following ssh config file:
 
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_drac_.md
new file mode 100644
index 00000000..c77e8d84
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_drac_.md
@@ -0,0 +1,72 @@
+Running the `mila init` command with this initial content:
+
+```
+# A comment in the file.
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'y')
+leads the following ssh config file:
+
+```
+# A comment in the file.
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_no_drac_.md
similarity index 92%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_no_drac_.md
index 38126088..f9384480 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_confirm_changes_no_drac_.md
@@ -5,7 +5,7 @@ Running the `mila init` command with this initial content:
 
 ```
 
-and these user inputs: ('bob\r', 'y')
+and these user inputs: ('bob\r', 'n', 'y')
 leads the following ssh config file:
 
 ```
@@ -13,7 +13,6 @@ leads the following ssh config file:
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -21,9 +20,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -34,14 +33,13 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_drac_.md
new file mode 100644
index 00000000..78f78257
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_drac_.md
@@ -0,0 +1,14 @@
+Running the `mila init` command with this initial content:
+
+```
+# A comment in the file.
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'n')
+leads the following ssh config file:
+
+```
+# A comment in the file.
+
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_no_drac_.md
similarity index 79%
rename from tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_no_drac_.md
index 90f6ca32..a817aff5 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_comment_reject_changes_no_drac_.md
@@ -5,7 +5,7 @@ Running the `mila init` command with this initial content:
 
 ```
 
-and these user inputs: ('bob\r', 'n')
+and these user inputs: ('bob\r', 'n', 'n')
 leads the following ssh config file:
 
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_drac_.md
new file mode 100644
index 00000000..0e23643d
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_drac_.md
@@ -0,0 +1,76 @@
+Running the `mila init` command with this initial content:
+
+```
+# a comment
+Host foo
+    HostName foobar.com
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'y')
+leads the following ssh config file:
+
+```
+# a comment
+Host foo
+    HostName foobar.com
+
+Host mila
+    HostName login.server.mila.quebec
+    PreferredAuthentications publickey,keyboard-interactive
+    Port 2222
+    ServerAliveInterval 120
+    ServerAliveCountMax 5
+    ControlMaster auto
+    ControlPath ~/.cache/ssh/%r@%h:%p
+    ControlPersist 600
+    User bob
+
+Host mila-cpu
+    Port 2222
+    ForwardAgent yes
+    StrictHostKeyChecking no
+    LogLevel ERROR
+    UserKnownHostsFile /dev/null
+    RequestTTY force
+    ConnectTimeout 600
+    ServerAliveInterval 120
+    ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+    RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+    User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+    HostName %h
+    ProxyJump mila
+    ControlMaster auto
+    ControlPath ~/.cache/ssh/%r@%h:%p
+    ControlPersist 600
+    User bob
+
+Host beluga cedar graham narval niagara
+    HostName %h.alliancecan.ca
+    ControlMaster auto
+    ControlPath ~/.cache/ssh/%r@%h:%p
+    ControlPersist 600
+    User bob
+
+Host !beluga  bc????? bg????? bl?????
+    ProxyJump beluga
+    User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+    ProxyJump cedar
+    User bob
+
+Host !graham  gra??? gra????
+    ProxyJump graham
+    User bob
+
+Host !narval  nc????? ng?????
+    ProxyJump narval
+    User bob
+
+Host !niagara nia????
+    ProxyJump niagara
+    User bob
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md
similarity index 93%
rename from tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md
index 172838bf..2d57c530 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_confirm_changes_no_drac_.md
@@ -7,7 +7,7 @@ Host foo
 
 ```
 
-and these user inputs: ('bob\r', 'y')
+and these user inputs: ('bob\r', 'n', 'y')
 leads the following ssh config file:
 
 ```
@@ -17,7 +17,6 @@ Host foo
 
 Host mila
     HostName login.server.mila.quebec
-    User bob
     PreferredAuthentications publickey,keyboard-interactive
     Port 2222
     ServerAliveInterval 120
@@ -25,9 +24,9 @@ Host mila
     ControlMaster auto
     ControlPath ~/.cache/ssh/%r@%h:%p
     ControlPersist 600
+    User bob
 
 Host mila-cpu
-    User bob
     Port 2222
     ForwardAgent yes
     StrictHostKeyChecking no
@@ -38,14 +37,13 @@ Host mila-cpu
     ServerAliveInterval 120
     ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
     RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+    User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
     HostName %h
-    User bob
     ProxyJump mila
-    ForwardAgent yes
-    ForwardX11 yes
     ControlMaster auto
     ControlPath ~/.cache/ssh/%r@%h:%p
     ControlPersist 600
+    User bob
 ```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_drac_.md b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_drac_.md
new file mode 100644
index 00000000..fd72a52e
--- /dev/null
+++ b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_drac_.md
@@ -0,0 +1,18 @@
+Running the `mila init` command with this initial content:
+
+```
+# a comment
+Host foo
+    HostName foobar.com
+
+```
+
+and these user inputs: ('bob\r', 'y', 'bob\r', 'n')
+leads the following ssh config file:
+
+```
+# a comment
+Host foo
+    HostName foobar.com
+
+```
diff --git a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_.md b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md
similarity index 82%
rename from tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_.md
rename to tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md
index a3304653..87835e84 100644
--- a/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_.md
+++ b/tests/cli/test_init_command/test_setup_ssh_has_different_indent_reject_changes_no_drac_.md
@@ -7,7 +7,7 @@ Host foo
 
 ```
 
-and these user inputs: ('bob\r', 'n')
+and these user inputs: ('bob\r', 'n', 'n')
 leads the following ssh config file:
 
 ```
diff --git a/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_accept_.md b/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_accept_.md
index d3ea3206..54f7c442 100644
--- a/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_accept_.md
+++ b/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_accept_.md
@@ -3,7 +3,6 @@ When this SSH config is already present in the WSL environment with these initia
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -11,9 +10,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -24,16 +23,42 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
 
 
@@ -44,14 +69,13 @@ leads the following ssh config file on the Windows side:
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
   ServerAliveCountMax 5
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -62,11 +86,34 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   remotecommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_reject_.md b/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_reject_.md
index 5aeff916..3610147c 100644
--- a/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_reject_.md
+++ b/tests/cli/test_init_command/test_setup_windows_ssh_config_from_wsl_reject_.md
@@ -3,7 +3,6 @@ When this SSH config is already present in the WSL environment with these initia
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -11,9 +10,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -24,16 +23,42 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
 
 
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..a26dc74f
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
@@ -0,0 +1,103 @@
+Running the `mila init` command with this initial content:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+
+Host mila-cpu
+  HostName login.server.mila.quebec
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName foooobar.com
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['y']
+leads to the following ssh config file:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+
+Host mila-cpu
+  HostName login.server.mila.quebec
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 69%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
index 2cb93738..c1188c05 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
@@ -13,7 +13,7 @@ Host *.server.mila.quebec !*login.server.mila.quebec
 
 ```
 
-and these user inputs: ['y']
+and these user inputs: ['y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
@@ -30,7 +30,6 @@ Host mila
 
 Host mila-cpu
   HostName login.server.mila.quebec
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -41,14 +40,40 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..daff7a18
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
@@ -0,0 +1,99 @@
+Running the `mila init` command with this initial content:
+
+```
+Host mila-cpu
+  HostName login.server.mila.quebec
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName foooobar.com
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['bob\r', 'y']
+leads to the following ssh config file:
+
+```
+Host mila-cpu
+  HostName login.server.mila.quebec
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 67%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
index 1c719ef2..265a0168 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
@@ -9,13 +9,12 @@ Host *.server.mila.quebec !*login.server.mila.quebec
 
 ```
 
-and these user inputs: ['bob\r', 'y']
+and these user inputs: ['bob\r', 'y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
 Host mila-cpu
   HostName login.server.mila.quebec
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -26,20 +25,18 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -47,4 +44,32 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..c1c922a0
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
@@ -0,0 +1,99 @@
+Running the `mila init` command with this initial content:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName foooobar.com
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['y']
+leads to the following ssh config file:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 67%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
index 1d510711..2b2687b2 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
@@ -10,7 +10,7 @@ Host *.server.mila.quebec !*login.server.mila.quebec
 
 ```
 
-and these user inputs: ['y']
+and these user inputs: ['y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
@@ -27,16 +27,13 @@ Host mila
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -47,4 +44,32 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..cd884b01
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
@@ -0,0 +1,95 @@
+Running the `mila init` command with this initial content:
+
+```
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName foooobar.com
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['bob\r', 'y']
+leads to the following ssh config file:
+
+```
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 65%
rename from tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
index 64b6bd4e..1be98519 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_has_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
@@ -6,23 +6,20 @@ Host *.server.mila.quebec !*login.server.mila.quebec
 
 ```
 
-and these user inputs: ['bob\r', 'y']
+and these user inputs: ['bob\r', 'y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -30,9 +27,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -43,4 +40,32 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..5ee14c97
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
@@ -0,0 +1,100 @@
+Running the `mila init` command with this initial content:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+
+Host mila-cpu
+  HostName login.server.mila.quebec
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['y']
+leads to the following ssh config file:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+
+Host mila-cpu
+  HostName login.server.mila.quebec
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 67%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
index 9a20d5dc..7ba79693 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
@@ -10,7 +10,7 @@ Host mila-cpu
 
 ```
 
-and these user inputs: ['y']
+and these user inputs: ['y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
@@ -27,7 +27,6 @@ Host mila
 
 Host mila-cpu
   HostName login.server.mila.quebec
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -38,14 +37,40 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..bda623a4
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
@@ -0,0 +1,96 @@
+Running the `mila init` command with this initial content:
+
+```
+Host mila-cpu
+  HostName login.server.mila.quebec
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['bob\r', 'y']
+leads to the following ssh config file:
+
+```
+Host mila-cpu
+  HostName login.server.mila.quebec
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 65%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
index 24155517..e22c7afa 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_has_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
@@ -6,13 +6,12 @@ Host mila-cpu
 
 ```
 
-and these user inputs: ['bob\r', 'y']
+and these user inputs: ['bob\r', 'y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
 Host mila-cpu
   HostName login.server.mila.quebec
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -23,10 +22,10 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -34,14 +33,40 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..91dfc64f
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_has_drac_entries_.md
@@ -0,0 +1,96 @@
+Running the `mila init` command with this initial content:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['y']
+leads to the following ssh config file:
+
+```
+Host mila
+  HostName login.server.mila.quebec
+  User bob
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
similarity index 65%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
index d015cf55..f15a1393 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_has_mila_entry_no_drac_entries_.md
@@ -7,7 +7,7 @@ Host mila
 
 ```
 
-and these user inputs: ['y']
+and these user inputs: ['y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
@@ -23,7 +23,6 @@ Host mila
   ControlPersist 600
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -34,14 +33,40 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
new file mode 100644
index 00000000..795c0373
--- /dev/null
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_has_drac_entries_.md
@@ -0,0 +1,92 @@
+Running the `mila init` command with this initial content:
+
+```
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+```
+
+and these user inputs: ['bob\r', 'y']
+leads to the following ssh config file:
+
+```
+
+# Compute Canada
+Host beluga cedar graham narval niagara
+  Hostname %h.alliancecan.ca
+  User bob
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+Host mist
+  Hostname mist.scinet.utoronto.ca
+  User bob
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
+
+Host mila
+  HostName login.server.mila.quebec
+  PreferredAuthentications publickey,keyboard-interactive
+  Port 2222
+  ServerAliveInterval 120
+  ServerAliveCountMax 5
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host mila-cpu
+  Port 2222
+  ForwardAgent yes
+  StrictHostKeyChecking no
+  LogLevel ERROR
+  UserKnownHostsFile /dev/null
+  RequestTTY force
+  ConnectTimeout 600
+  ServerAliveInterval 120
+  ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
+  RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
+
+Host *.server.mila.quebec !*login.server.mila.quebec
+  HostName %h
+  ProxyJump mila
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+```
\ No newline at end of file
diff --git a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_.md b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
similarity index 63%
rename from tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_.md
rename to tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
index 1f20cd11..bf9a28c4 100644
--- a/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_.md
+++ b/tests/cli/test_init_command/test_with_existing_entries_no_mila_compute_entry_no_mila_cpu_entry_no_mila_entry_no_drac_entries_.md
@@ -1,13 +1,12 @@
 Running the `mila init` command with no initial ssh config file
 
-and these user inputs: ['bob\r', 'y']
+and these user inputs: ['bob\r', 'y', 'bob\r', 'y']
 leads to the following ssh config file:
 
 ```
 
 Host mila
   HostName login.server.mila.quebec
-  User bob
   PreferredAuthentications publickey,keyboard-interactive
   Port 2222
   ServerAliveInterval 120
@@ -15,9 +14,9 @@ Host mila
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
 
 Host mila-cpu
-  User bob
   Port 2222
   ForwardAgent yes
   StrictHostKeyChecking no
@@ -28,14 +27,40 @@ Host mila-cpu
   ServerAliveInterval 120
   ProxyCommand ssh mila "/cvmfs/config.mila.quebec/scripts/milatools/slurm-proxy.sh mila-cpu --mem=8G"
   RemoteCommand /cvmfs/config.mila.quebec/scripts/milatools/entrypoint.sh mila-cpu
+  User bob
 
 Host *.server.mila.quebec !*login.server.mila.quebec
   HostName %h
-  User bob
   ProxyJump mila
-  ForwardAgent yes
-  ForwardX11 yes
   ControlMaster auto
   ControlPath ~/.cache/ssh/%r@%h:%p
   ControlPersist 600
+  User bob
+
+Host beluga cedar graham narval niagara
+  HostName %h.alliancecan.ca
+  ControlMaster auto
+  ControlPath ~/.cache/ssh/%r@%h:%p
+  ControlPersist 600
+  User bob
+
+Host !beluga  bc????? bg????? bl?????
+  ProxyJump beluga
+  User bob
+
+Host !cedar   cdr? cdr?? cdr??? cdr????
+  ProxyJump cedar
+  User bob
+
+Host !graham  gra??? gra????
+  ProxyJump graham
+  User bob
+
+Host !narval  nc????? ng?????
+  ProxyJump narval
+  User bob
+
+Host !niagara nia????
+  ProxyJump niagara
+  User bob
 ```
\ No newline at end of file
diff --git a/tests/cli/test_local.py b/tests/cli/test_local.py
index 854be276..783f74de 100644
--- a/tests/cli/test_local.py
+++ b/tests/cli/test_local.py
@@ -1,14 +1,19 @@
 from __future__ import annotations
 
-import sys
 from subprocess import PIPE
 
 import pytest
 from pytest_regressions.file_regression import FileRegressionFixture
 
-from milatools.cli.local import CommandNotFoundError, Local
+from milatools.cli.local import CommandNotFoundError, Local, check_passwordless
 
-from .common import output_tester, requires_no_s_flag, xfails_on_windows
+from .common import (
+    output_tester,
+    passwordless_ssh_connection_to_localhost_is_setup,
+    requires_no_s_flag,
+    skip_param_if_on_github_ci,
+    xfails_on_windows,
+)
 
 _ECHO_CMD = pytest.param(
     ["echo", "--arg1", "val1", "--arg2=val2", "X"],
@@ -32,6 +37,17 @@ def test_display(
     output_tester(lambda: (Local().display(cmd), None), capsys, file_regression)
 
 
+prints_unexpected_text_to_stdout_on_windows = xfails_on_windows(
+    raises=AssertionError,
+    strict=False,
+    reason=(
+        "BUG: There is somehow some text being printed to stdout during this test on "
+        "windows."
+    ),
+)
+
+
+@prints_unexpected_text_to_stdout_on_windows
 @pytest.mark.parametrize("cmd", [_ECHO_CMD])
 def test_silent_get(
     cmd: list[str],
@@ -41,6 +57,7 @@ def test_silent_get(
     output_tester(lambda: (Local().silent_get(*cmd), None), capsys, file_regression)
 
 
+@prints_unexpected_text_to_stdout_on_windows
 @requires_no_s_flag
 @pytest.mark.parametrize("cmd", [_ECHO_CMD])
 def test_get(
@@ -51,10 +68,7 @@ def test_get(
     output_tester(lambda: (Local().get(*cmd), None), capsys, file_regression)
 
 
-@pytest.mark.skipif(
-    sys.platform == "win32",
-    reason="TODO: The output of this test varies between Windows and Ubuntu.",
-)
+@prints_unexpected_text_to_stdout_on_windows
 @requires_no_s_flag
 @pytest.mark.parametrize("cmd", [_ECHO_CMD, _FAKE_CMD, _FAIL_CODE_CMD])
 def test_run(
@@ -81,6 +95,7 @@ def _catch_exc():
         output_tester(func, capsys, file_regression)
 
 
+@prints_unexpected_text_to_stdout_on_windows
 @requires_no_s_flag
 @pytest.mark.parametrize("cmd", [_ECHO_CMD])
 def test_popen(
@@ -93,3 +108,20 @@ def test_popen(
         capsys,
         file_regression,
     )
+
+
+@pytest.mark.parametrize(
+    ("hostname", "expected"),
+    [
+        ("localhost", passwordless_ssh_connection_to_localhost_is_setup),
+        ("blablabob@localhost", False),
+        skip_param_if_on_github_ci("narval", True),
+        skip_param_if_on_github_ci("blablabob@narval", False),
+        skip_param_if_on_github_ci("beluga", True),
+        skip_param_if_on_github_ci("cedar", True),
+        skip_param_if_on_github_ci("graham", True),
+        skip_param_if_on_github_ci("niagara", False),  # Not enabled by default.
+    ],
+)
+def test_check_passwordless(hostname: str, expected: bool):
+    assert check_passwordless(hostname) == expected
diff --git a/tests/cli/test_remote.py b/tests/cli/test_remote.py
index 58ba2ff6..3d4884fa 100644
--- a/tests/cli/test_remote.py
+++ b/tests/cli/test_remote.py
@@ -11,11 +11,9 @@
 from unittest.mock import Mock
 
 import invoke
-import paramiko.ssh_exception
 import pytest
 from fabric.connection import Connection
 from pytest_regressions.file_regression import FileRegressionFixture
-from typing_extensions import ParamSpec
 
 from milatools.cli.remote import (
     QueueIO,
@@ -25,33 +23,17 @@
 )
 from milatools.cli.utils import T, shjoin
 
-from .common import function_call_string, requires_s_flag
-
-P = ParamSpec("P")
-
-passwordless_ssh_connection_to_localhost_is_setup = False
-
-try:
-    Connection("localhost").open()
-except (
-    paramiko.ssh_exception.SSHException,
-    paramiko.ssh_exception.NoValidConnectionsError,
-):
-    pass
-else:
-    passwordless_ssh_connection_to_localhost_is_setup = True
+from .common import (
+    function_call_string,
+    requires_s_flag,
+    requires_ssh_to_localhost,
+)
 
 
 @pytest.fixture(
     scope="session",
     params=[
-        pytest.param(
-            "localhost",
-            marks=pytest.mark.skipif(
-                not passwordless_ssh_connection_to_localhost_is_setup,
-                reason="Passwordless ssh access to localhost needs to be setup.",
-            ),
-        ),
+        pytest.param("localhost", marks=requires_ssh_to_localhost),
         # TODO: Think about a smart way to enable this. Some tests won't work as-is.
         # pytest.param(
         #     "mila",
@@ -261,7 +243,9 @@ def test_remote_transform_methods(
 
 @pytest.fixture(scope="function")
 def remote(mock_connection: Connection):
-    return Remote(hostname=mock_connection.host, connection=mock_connection)
+    hostname = mock_connection.host
+    assert isinstance(hostname, str)
+    return Remote(hostname=hostname, connection=mock_connection)
 
 
 @pytest.mark.parametrize("message", ["foobar"])