Hey there UltegraDi2,
Thanks for reaching out to the Apple Support Communities. To get started, have you gone through the steps listed in the 'Related Article', under the "Get help" section?
About the 'Trust This Computer' alert on your iPhone, iPad, or iPod touch - Apple Support
If you tap Trust or Don't Trust but doesn't accept your answer, or if the Trust alert won't appear, follow these steps. Try again after each:
1. Make sure that your computer has the latest version of macOS or the latest version of iTunes.
2. Disconnect and reconnect your device from your computer.
3. Restart your computer.
4. Restart your device:
- iPhone
5. Reset your Trust settings.
If the above steps don't help, go to Settings > General > Transfer or Reset [Device] > Reset and tap Reset Network Settings. This also resets Wi-Fi networks and passwords, cellular settings, and VPN and APN settings that you’ve used before.
If you downloaded iTunes for Windows from the Microsoft Store, make sure that iTunes Mobile Device Helper is enabled as a startup item.
If still unable to trust your MacBook with the step above, try testing the issue in safe mode. Safe mode can help to determine if the issue may be caused by some software that has loaded when starting your MacBook.
For steps on how to boot into safe mode, and what to do if the issue does or doesn't occur in safe mode, check out this next link here: How to use safe mode on your Mac - Apple Support
Keep us updated on the results.
Take care!