diff --git a/web/packages/teleterm/src/agentCleanupDaemon/agentCleanupDaemon.test.ts b/web/packages/teleterm/src/agentCleanupDaemon/agentCleanupDaemon.test.ts
index 997abd394c699..4a9d7001a61f1 100644
--- a/web/packages/teleterm/src/agentCleanupDaemon/agentCleanupDaemon.test.ts
+++ b/web/packages/teleterm/src/agentCleanupDaemon/agentCleanupDaemon.test.ts
@@ -1,3 +1,6 @@
+/**
+ * @jest-environment node
+ */
 /**
  * Teleport
  * Copyright (C) 2023  Gravitational, Inc.
diff --git a/web/packages/teleterm/src/mainProcess/agentDownloader/fileDownloader.test.ts b/web/packages/teleterm/src/mainProcess/agentDownloader/fileDownloader.test.ts
index e1171c33956d8..7f9af2d97c133 100644
--- a/web/packages/teleterm/src/mainProcess/agentDownloader/fileDownloader.test.ts
+++ b/web/packages/teleterm/src/mainProcess/agentDownloader/fileDownloader.test.ts
@@ -1,5 +1,5 @@
 /**
- * @jest-environment jsdom
+ * @jest-environment node
  */
 /**
  * Teleport
diff --git a/web/packages/teleterm/src/mainProcess/createAgentConfigFile.test.ts b/web/packages/teleterm/src/mainProcess/createAgentConfigFile.test.ts
index a11f29d1eec4a..30ecda05521bc 100644
--- a/web/packages/teleterm/src/mainProcess/createAgentConfigFile.test.ts
+++ b/web/packages/teleterm/src/mainProcess/createAgentConfigFile.test.ts
@@ -1,3 +1,6 @@
+/**
+ * @jest-environment node
+ */
 /**
  * Teleport
  * Copyright (C) 2023  Gravitational, Inc.
@@ -24,6 +27,7 @@ import { makeRuntimeSettings } from 'teleterm/mainProcess/fixtures/mocks';
 
 import {
   createAgentConfigFile,
+  disableDebugServiceStanza,
   generateAgentConfigPaths,
 } from './createAgentConfigFile';
 
@@ -34,10 +38,12 @@ beforeEach(() => {
   jest
     .spyOn(childProcess, 'execFile')
     .mockImplementation((command, args, options, callback) => {
-      callback(undefined, '', '');
-      return this;
+      callback(null, '', '');
+      return undefined;
     });
   jest.spyOn(fs, 'rm').mockImplementation(() => Promise.resolve());
+  jest.spyOn(fs, 'mkdir').mockImplementation(() => Promise.resolve(undefined));
+  jest.spyOn(fs, 'writeFile').mockImplementation(() => Promise.resolve());
 });
 
 test('teleport configure is called with proper arguments', async () => {
@@ -69,7 +75,7 @@ test('teleport configure is called with proper arguments', async () => {
     [
       'node',
       'configure',
-      `--output=${userDataDir}/agents/cluster.local/config.yaml`,
+      `--output=stdout`,
       `--data-dir=${userDataDir}/agents/cluster.local/data`,
       `--proxy=${proxy}`,
       `--token=${token}`,
@@ -80,6 +86,13 @@ test('teleport configure is called with proper arguments', async () => {
     },
     expect.anything()
   );
+  expect(fs.writeFile).toHaveBeenCalledWith(
+    `${userDataDir}/agents/cluster.local/config.yaml`,
+    // It'd be nice to make childProcess.execFile return certain output and then verify that this
+    // argument includes that output + disableDebugServiceStanza. Alas, the promisified version of
+    // execFile isn't easily mockable – stdout in tests is just "undefined" for some reason.
+    expect.stringContaining(disableDebugServiceStanza)
+  );
 });
 
 test('previous config file is removed before calling teleport configure', async () => {
diff --git a/web/packages/teleterm/src/mainProcess/createAgentConfigFile.ts b/web/packages/teleterm/src/mainProcess/createAgentConfigFile.ts
index f5aaf05a5289b..4345563e3ee7f 100644
--- a/web/packages/teleterm/src/mainProcess/createAgentConfigFile.ts
+++ b/web/packages/teleterm/src/mainProcess/createAgentConfigFile.ts
@@ -52,12 +52,12 @@ export async function createAgentConfigFile(
     .map(keyAndValue => keyAndValue.join('='))
     .join(',');
 
-  await asyncExecFile(
+  const { stdout } = await asyncExecFile(
     runtimeSettings.agentBinaryPath,
     [
       'node',
       'configure',
-      `--output=${configFile}`,
+      '--output=stdout',
       `--data-dir=${dataDirectory}`,
       `--proxy=${args.proxy}`,
       `--token=${args.token}`,
@@ -67,8 +67,42 @@ export async function createAgentConfigFile(
       timeout: 10_000, // 10 seconds
     }
   );
+
+  try {
+    await fs.mkdir(path.dirname(configFile), {
+      // Create the agents dir too if it doesn't already exist.
+      recursive: true,
+    });
+  } catch (error) {
+    // Ignore error if directory already exists.
+    if (error['code'] !== 'EEXIST') {
+      throw error;
+    }
+  }
+
+  await fs.writeFile(configFile, stdout + disableDebugServiceStanza);
 }
 
+// The debug service is enabled by default. It starts when the teleport agent is launched and it
+// creates a debug.sock file in the data directory. Unfortunately, there's a length limit on the
+// socket path – 107 characters on Linux and 104 characters on macOS [1]. If exceeded, creating a
+// new listener fails with "bind: invalid argument".
+//
+// The default path for debug.sock for Connect My Computer on macOS is
+// /Users/<user>/Library/Application Support/Teleport Connect/agents/<proxy hostname>/data/debug.sock
+// The constant part is 76 characters which leaves just 28 characters for the hostname and user.
+//
+// As a workaround, we disable the debug service. This is going to work until someone adds another
+// socket which is crucial to run a Teleport agent.
+//
+// See the GitHub issue for more details: https://github.com/gravitational/teleport/issues/43250
+//
+// [1] https://unix.stackexchange.com/questions/367008/why-is-socket-path-length-limited-to-a-hundred-chars
+export const disableDebugServiceStanza = `
+debug_service:
+  enabled: false
+`;
+
 export async function removeAgentDirectory(
   runtimeSettings: RuntimeSettings,
   rootClusterUri: RootClusterUri
diff --git a/web/packages/teleterm/src/mainProcess/terminateWithTimeout/terminateWithTimeout.test.ts b/web/packages/teleterm/src/mainProcess/terminateWithTimeout/terminateWithTimeout.test.ts
index 6138dc074d95d..e26a7fd20e5c2 100644
--- a/web/packages/teleterm/src/mainProcess/terminateWithTimeout/terminateWithTimeout.test.ts
+++ b/web/packages/teleterm/src/mainProcess/terminateWithTimeout/terminateWithTimeout.test.ts
@@ -1,3 +1,6 @@
+/**
+ * @jest-environment node
+ */
 /**
  * Teleport
  * Copyright (C) 2023  Gravitational, Inc.
diff --git a/web/packages/teleterm/src/services/grpcCredentials/makeCert/makeCert.test.ts b/web/packages/teleterm/src/services/grpcCredentials/makeCert/makeCert.test.ts
index b7aa3e437297f..2a7c6358a4ba5 100644
--- a/web/packages/teleterm/src/services/grpcCredentials/makeCert/makeCert.test.ts
+++ b/web/packages/teleterm/src/services/grpcCredentials/makeCert/makeCert.test.ts
@@ -1,3 +1,6 @@
+/**
+ * @jest-environment node
+ */
 /**
  * (The MIT License)
  *