There is a 'vscode remote' issue with related symptoms that go back all the way to 2024: https://github.com/microsoft/vscode-remote-release/issues/10441 The users reported that they were not being prompted and had to reset permissions manually in the settings. April 3rd, someone reported that the issue got worse as they were not able to reset permissions. They had to boot in recovery mode and delete some obscure file: /Volumes/Data/Library/Preferences/com.apple.networkextension.plist On my system, this file does not even appear to exist. I'm currently on Tahoe 26.5.2