I have reproduced the issue on the latest CLI version.
Yes, I am on the latest version
I have searched existing posts and this report is not a duplicate.
Yes, this isn’t a duplicate
In which of these areas are you experiencing a problem?
Other
Expected behavior
Update the toolkit?
Actual behavior
“Failed to update” constantly shows in VS Code
Reproduction steps
Windows 11
Install VS Code
Could be user related, I don’t run from an Admin Account.
Verbose output
None, “show output” gives nothing useful
Operating system
Windows 11
CLI version
4.6.0
Shell
N/A
Nodejs version
26.4.0
What language and version are you using in your application?
N/A
Hi @ceri_waters – Can you provide the details from Show Output?
@NickWesselman It shows a big fat nothing 
How often is this error displaying? Is it random, on startup, or when opening specific interfaces?
Can you try this?
-
Open your Command Palette by pressing Ctrl+Shift+P (Windows/Linux) or Cmd+Shift+P (macOS).
-
Type and select Developer: Open Logs Folder.
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This will launch your system’s file manager (File Explorer or Finder) directly inside the folder where VS Code stores its active text logs.
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Grab that folder path and open it in a new VSCode window.
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Press Ctrl+Shift+F (Windows/Linux) or Cmd+Shift+F (macOS) to open the Global Search view.
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Search for shopify-ai-toolkit and see if any logs have additional details.
Everytime I start VS Code, I don’t think it’s ever actually updated 
My machine was wiped a couple of weeks back too, and even before then it failed 
Nothing Shopify related in that log, the only warning is:
`2026-08-06 15:23:06.564 [warning] updateWindowsJumpList#setJumpList unexpected result: customCategoryAccessDeniedError`
Are you on the latest VSCode? What if you remove / re-add the plugin?
