Windows: VS Code Insiders requires two restarts to update, if an update is already pending and another is available #268531
Description
Type: Bug
Every time when I tried to update vs code insiders to new version through clicking the gear icon, it didn't install the update during the restarting time. Instead, after it restarted, it started to install the update in the background. After a few minutes, the "1" icon will pop up on the gear icon, and I need to restart it again to have it installed. I don't have this issue when using the stable version.
VS Code version: Code - Insiders 1.105.0-insider (afe5914, 2025-09-25T05:05:49.513Z)
OS version: Windows_NT x64 10.0.26200
Modes:
System Info
| Item | Value |
|---|---|
| CPUs | Intel(R) Xeon(R) Platinum 8370C CPU @ 2.80GHz (16 x 2793) |
| GPU Status | 2d_canvas: unavailable_software direct_rendering_display_compositor: disabled_off_ok gpu_compositing: disabled_software multiple_raster_threads: enabled_on opengl: disabled_off rasterization: disabled_software raw_draw: disabled_off_ok skia_graphite: disabled_off trees_in_viz: disabled_off video_decode: disabled_software video_encode: disabled_software vulkan: disabled_off webgl: unavailable_software webgl2: unavailable_software webgpu: unavailable_software webnn: unavailable_software |
| Load (avg) | undefined |
| Memory (System) | 63.95GB (40.06GB free) |
| Process Argv | |
| Screen Reader | no |
| VM | 0% |
Extensions (28)
| Extension | Author (truncated) | Version |
|---|---|---|
| Bookmarks | ale | 13.5.0 |
| markdown-mermaid | bie | 1.29.0 |
| vulnerability-extension | dev | 1.2025.918001 |
| copilot | Git | 1.376.1794 |
| copilot-chat | Git | 0.32.2025092509 |
| remotehub | Git | 0.64.0 |
| vscode-drawio | hed | 1.9.0 |
| rest-client | hum | 0.25.1 |
| vscode-azure-github-copilot | ms- | 1.0.117 |
| vscode-azure-mcp-server | ms- | 0.8.2 |
| vscode-azureresourcegroups | ms- | 0.11.4 |
| vscode-bicep | ms- | 0.37.4 |
| csdevkit | ms- | 1.50.51 |
| csharp | ms- | 2.90.60 |
| vscode-dotnet-runtime | ms- | 2.3.7 |
| debugpy | ms- | 2025.10.0 |
| python | ms- | 2025.14.0 |
| vscode-pylance | ms- | 2025.8.2 |
| vscode-python-envs | ms- | 1.8.0 |
| remote-explorer | ms- | 0.5.0 |
| remote-repositories | ms- | 0.42.0 |
| remote-server | ms- | 1.5.3 |
| vscode-speech | ms- | 0.16.0 |
| excalidraw-editor | pom | 3.9.0 |
| markdown-preview-enhanced | shd | 0.8.19 |
| code-spell-checker | str | 4.2.6 |
| fugio | Tyl | 0.0.7 |
| vim | vsc | 1.30.1 |