Hi Ryan,
Seeing your description, I hope it's safe to assume you've tried all the suggestions mentioned by the AI answer. If yes, then maybe you need to try a deeper solution. Let's reinstall Windows (keeping files and apps)
- Clear up pending instances of previous update attempts:
- Re-run the clearing Windows Update cache commands you previously did.
- Open Disk Cleanup (Admin) > Clean up system files > Temp files and Windows Update.
- Use the built-in repair option
- Open Settings > System > Recovery > Fix problems using Windows Update
- Click Reinstall now > follow the onscreen instructions to reinstall Windows.
- If that fails, perform an in-place upgrade
- Since you tagged this as Insider: Using ISOs - Windows Insider Program | Microsoft Learn
- Check Settings > Windows Update > Windows Insider Program
- Mount the ISO > run
setup.exefile to launch the install process. - Select Keep Windows settings, personal files, and apps option.
- Note: If you're actually not in Insider, let me know.
Disclaimer: Both Windows reinstallation and in-place upgrade will refresh your Windows files and operating system without removing files or applications. That being said, we always recommend that if you have important data, you should back it up first before making large system changes.
If even the reinstallation doesn't work, unfortunately you might actually need to contact support. I know you've ran into a loop, so please check out this path to see if it can get you to someone you can talk to:
- Sign in with your account at Contact Us - Microsoft Support
- Enter / choose an issue > click Get Help to make a request
- Scroll down > click Ask our Support Assistant and follow guidance
- If the issue persists, specifically state in the chat box that you need direct help.
- The Contact Support button should appear > click it > select the chat in browser option.
Note: The support contact team only works at certain times, so if the last window shows that it's unavailable, try opening it again the next day. If you prefer phone support, you can leave a phone number. This way, they can call you and help you. If you don't see chat option, choose another category and ask to escalate.
That might get you out the loop you've been in.