"docker desktop start" cli command locks up if attempted on a remote winrm powershell session

[matt-coad-rp]

Description

Docker desktop cannot be started using a remote powershell session connected via WinRM.

Attempts using either the docker desktop cli commands or running the "Docker Desktop.exe" manually both fail.

Reproduce

• Create an Azure VM using Windows 11 Enterprise OS. (Sku win11-22h2-entn)
• Ensure it supports access via WinRM and can connect remotely via RDP.
• Login into the VM's desktop.
• Install docker desktop 4.37 using Wsl v2 on an Ubuntu-24.04 distro
• Set docker desktop to not login automatically nor start the UI automaticall.
• Stop docker desktop
• Connect to the Azure VM using powershell remoting using the same account.
• Run the command "docker desktop start"

The console messages that its starting docker desktop will not be displayed.
The command locks up indefinitely (Waited for over 10 minutes)

Expected behavior

"docker desktop start" completes successfully and docker desktop is started and docker commands can run without locking up.

docker version

Client:
 Version:           27.4.0
 API version:       1.47
 Go version:        go1.22.10
 Git commit:        bde2b89
 Built:             Sat Dec  7 10:40:21 2024
 OS/Arch:           windows/amd64
 Context:           desktop-linux

Server: Docker Desktop 4.37.1 (178610)
 Engine:
  Version:          27.4.0
  API version:      1.47 (minimum version 1.24)
  Go version:       go1.22.10
  Git commit:       92a8393
  Built:            Sat Dec  7 10:38:57 2024
  OS/Arch:          linux/amd64
  Experimental:     false
 containerd:
  Version:          1.7.21
  GitCommit:        472731909fa34bd7bc9c087e4c27943f9835f111
 runc:
  Version:          1.1.13
  GitCommit:        v1.1.13-0-g58aa920
 docker-init:
  Version:          0.19.0
  GitCommit:        de40ad0

docker info

Client:
 Version:    27.4.0
 Context:    desktop-linux
 Debug Mode: false
 Plugins:
  ai: Ask Gordon - Docker Agent (Docker Inc.)
    Version:  v0.5.1
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-ai.exe
  buildx: Docker Buildx (Docker Inc.)
    Version:  v0.19.2-desktop.1
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-buildx.exe
  compose: Docker Compose (Docker Inc.)
    Version:  v2.31.0-desktop.2
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-compose.exe
  debug: Get a shell into any image or container (Docker Inc.)
    Version:  0.0.37
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-debug.exe
  desktop: Docker Desktop commands (Beta) (Docker Inc.)
    Version:  v0.1.0
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-desktop.exe
  dev: Docker Dev Environments (Docker Inc.)
    Version:  v0.1.2
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-dev.exe
  extension: Manages Docker extensions (Docker Inc.)
    Version:  v0.2.27
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-extension.exe
  feedback: Provide feedback, right in your terminal! (Docker Inc.)
    Version:  v1.0.5
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-feedback.exe
  init: Creates Docker-related starter files for your project (Docker Inc.)
    Version:  v1.4.0
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-init.exe
  sbom: View the packaged-based Software Bill Of Materials (SBOM) for an image (Anchore Inc.)
    Version:  0.6.0
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-sbom.exe
  scout: Docker Scout (Docker Inc.)
    Version:  v1.15.1
    Path:     C:\Users\StationAdmin\.docker\cli-plugins\docker-scout.exe

Server:
 Containers: 96
  Running: 54
  Paused: 0
  Stopped: 42
 Images: 36
 Server Version: 27.4.0
 Storage Driver: overlay2
  Backing Filesystem: extfs
  Supports d_type: true
  Using metacopy: false
  Native Overlay Diff: true
  userxattr: false
 Logging Driver: json-file
 Cgroup Driver: cgroupfs
 Cgroup Version: 1
 Plugins:
  Volume: local
  Network: bridge host ipvlan macvlan null overlay
  Log: awslogs fluentd gcplogs gelf journald json-file local splunk syslog
 CDI spec directories:
  /etc/cdi
  /var/run/cdi
 Swarm: inactive
 Runtimes: io.containerd.runc.v2 nvidia runc
 Default Runtime: runc
 Init Binary: docker-init
 containerd version: 472731909fa34bd7bc9c087e4c27943f9835f111
 runc version: v1.1.13-0-g58aa920
 init version: de40ad0
 Security Options:
  seccomp
   Profile: unconfined
 Kernel Version: 5.15.153.1-microsoft-standard-WSL2
 Operating System: Docker Desktop
 OSType: linux
 Architecture: x86_64
 CPUs: 8
 Total Memory: 31.35GiB
 Name: docker-desktop
 ID: 6bb59b64-f5c0-45af-a364-3b74bfbc1334
 Docker Root Dir: /var/lib/docker
 Debug Mode: false
 HTTP Proxy: http.docker.internal:3128
 HTTPS Proxy: http.docker.internal:3128
 No Proxy: hubproxy.docker.internal
 Labels:
  com.docker.desktop.address=npipe://\\.\pipe\docker_cli
 Experimental: false
 Insecure Registries:
  hubproxy.docker.internal:5555
  127.0.0.0/8
 Live Restore Enabled: false

WARNING: No blkio throttle.read_bps_device support
WARNING: No blkio throttle.write_bps_device support
WARNING: No blkio throttle.read_iops_device support
WARNING: No blkio throttle.write_iops_device support
WARNING: daemon is not using the default seccomp profile

Diagnostics ID

9400C291-C06A-44F1-B38A-E07D15238F3F/20250108030507

Additional Info

Its possible to put docker into odd states where commands like "docker info" will wait indefinitely. I've done a lot of mucking around but I think
I attempted to started docker by doing a Start-Process on the "Docker Desktop.exe".

Also managed to get it into state where "docker desktop status" says docker is stopped, but "docker desktop start" says its already running.