Hey again! No problem for me at all.
I was just thinking of a common denominator, since the same behavior happens on multiple Mac’s even multiple iOS devices. And no clear pattern in relation to the OS/iOS versions.
So was wondering if it’s a networking issue or setting. Or even an iPhone Setting or app, that you both have configured, or sync with.
This may not help, but with your phone, could you try first, resetting the Privacy and Location Settings on your phone, (After disconnecting it from your Mac):
https://support.apple.com/guide/iphone/return-iphone-settings-to-their-defaults-iphea1c2fe48/ios
Then re-connect it again, open Finder and select “Trust” again, then test with Image Capture again?
Resetting All Settings maybe another valid step.
However if you think it’s solely related to the Mac, (I’ve seen both scenarios several times), I would clear out your Mac’s Cache:
Open Finder.
While holding Option on the keyboard, click Go > Library.
Open Caches.
Delete the contents.
Restart.
Test.
In fact, I may even try that one before resetting the settings on iOS.
I’d give those a shot if you haven’t given up yet, they only take a few minutes, likewise, we’re you able to test in a new user?
Hope there’s a quick fix somewhere here, best of luck, you can always contact Apple Care by phone though also, (One of the few companies that offer actual human phone support), they can also guide you to the right place if need be. Let me know how it goes, I’ve been there, good luck!