Ol'Jedi Said:
"Trust This Computer: This trust the computer prompt also happens when devices are on wireless charger connected via wifi."
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Caches being the Culprit:
I. iPhone:
Clear "System Data" ("Other"):
Clear the storage named "System Data" (formerly named "Other"). It basically contains unnecessary files such as caches that are used for system ease of use - all of which gather over time. Use my Muser Tip: How to Clear "Other" in your iPhone's Storage - Use Backup - User Tip. Caches would be being used for remembrance of application use. So, clearing other may be the way to go about this, as it would be performs through use of a computer.
II. Mac:
Try the Following in the Order Provided:
- Create a New Administrator User:
Create a new Administrator user and see what happens. If it does not occur, then it is something configured in your current user. Create this as the Administrator in: System Preferences > Users & Groups
Try logging in using Safe Mode (Hold down shift key upon boot). See if you can log in. Items only load as they do by default, while you are booted into Safe Mode. All caches are set aside. Go Here: Use Safe Mode to Isolate Issues with your Mac - Apple Support
Nothing would be deleted. It's just that items that have become corrupted or deleted, would be placed back to where they should be. Go Here: How to Reinstall macOS from macOS Recovery - Apple Support