• VSCode Version: 1.47.2
• OS Version: Windows 10.0.18363 Build 18363

Steps to Reproduce:

1. Set the debug toolbar to docked in the settings.
2. Debug a Node project using node --inspect-brk=127.0.0.1:9223
3. Debug a React project using Debugger for Chrome
4. Once both projects have started up, select each project from the menu in the debug toolbar.
5. Observe that the icon sometimes gets "stuck" as a red square rather than switching between "disconnect" (for the React project) and "stop" (for the Node project).
6. Now switch to the debug toolbar to floating, and note that the icon now correctly updates.

Does this issue occur when all extensions are disabled?: Not possible to test because Debugger for Chrome is required to reproduce this bug

Reference: #99786 (comment)