Steps to Reproduce:

I previously had this issue on a code-insiders release from a day or so ago, downloaded the latest insiders build, but having the problem again today.
Does this issue occur when all extensions are disabled?: Yes
(Experimental duplicate detection)
Thanks for submitting this issue. Please also check if it is already covered by an existing one, like:
Please check https://github.com/Microsoft/vscode/issues/7426#issuecomment-425093469
@joaomoreno The app is already in the Applications folder...
I ran the two commands, the first one failed with:
chown: /Users/tom/Library/Caches/com.microsoft.VSCode.ShipIt/*: No such file or directory
However it runs OK if I drop the asterisk:
sudo chown $USER ~/Library/Caches/com.microsoft.VSCode.ShipIt/
The second one seemed to run ok, but has had no effect on my ability to update, I still get permission denied. To be clear, I ran it for Code Insiders:
xattr -dr com.apple.quarantine /Applications/Visual\ Studio\ Code\ -\ Insiders.app
When I run ps to see where Code Insiders is running from, it shows that it's running from /Applications/Visual Studio Code - Insiders.app as expected. Any other ideas?
Make sure Code isn't running. Then, run it from the Terminal as code --verbose, then run an update. The specific error should come up in the terminal, maybe it contains more info.
Also what does ls -la ~/Library/Caches/com.microsoft.VSCode.ShipIt return?
Running in verbose mode I get this when checking for updates:
[main 2:29:36 PM] update#checkForUpdates, state = idle
[main 2:29:36 PM] update#setState checking for updates
[main 2:29:36 PM] telemetry/workbenchActionExecuted { id: 'CheckForUpdate', from: 'menu' }
[main 2:29:36 PM] menubarService#updateMenubar 1
[main 2:29:37 PM] update#setState downloading
[main 2:29:37 PM] UpdateService error: Could not create temporary directory: Permission denied
[main 2:29:37 PM] update#setState idle
[1962:1130/142937.132645:INFO:CONSOLE(2465)] "Could not create temporary directory: Permission denied", source: file:///Applications/Visual Studio Code - Insiders.app/Contents/Resources/app/out/vs/workbench/workbench.main.js (2465)
[main 2:29:37 PM] menubarService#updateMenubar 1
The output from that ls command is:
drwxr-xr-x 2 tom staff 64 Nov 19 10:35 .
drwx------+ 88 tom staff 2816 Nov 30 12:05 ..
What about $TMPDIR, does your user have permissions there?
@joaomoreno Yep, just verified I can write there.
Oh I just noticed you are on Insiders. Run this one:
ls -la ~/Library/Caches/com.microsoft.VSCodeInsiders.ShipIt
@joaomoreno That command returns nothing at all. I tried to cd into it, and received a permission denied, so I then ran:
sudo chown $USER ~/Library/Caches/com.microsoft.VSCodeInsiders.ShipIt/
Restarted the insiders build, and now the software update works!
Sorry about the run-around, I didn't realize there was a ShipIt directory for both kinds of builds... Thanks for the help!
Most helpful comment
@joaomoreno That command returns nothing at all. I tried to
cdinto it, and received a permission denied, so I then ran:sudo chown $USER ~/Library/Caches/com.microsoft.VSCodeInsiders.ShipIt/Restarted the insiders build, and now the software update works!
Sorry about the run-around, I didn't realize there was a ShipIt directory for both kinds of builds... Thanks for the help!