At what point did Claude fail with that, generating a list of events from the scan, or adding the events to the calendar?
I had a different AI (Grok) successfully take a prompt like "I live at this address and need to pick up my son from school at 2:30pm, and then we need to hit these three stores before heading back home. Find the path with the least driving and add all of these as discrete events to my calendar with their addresses embedded, and give me a google maps link with the full path so I can double-check". Did it correctly on the first try. I'd think other AIs could do that too. So I'm thinking it was the scanned image that gave it problems?
The failure is that the task was "can I take a picture of a printed calendar with Claude and have events added to my shared family calendar" and it is apparently not possible. The parsed file was fine, and maybe would have needed a few touchups, but Claude could not access the calendar directly, and Apple Calendar cannot read its own calendar format. So, failure, no partial credit given. My wife manually added the calendar in the time required it was taking me to debug this nonsense; I probably said "wait, no, it's almost done!" a half dozen times before throwing up my hands.
The added benefit of this failure is that by adding it by hand, we were much more familiar with the events on the calendar, and were ready for a few "outlier" events, e.g. a tournament 100 miles away that we knew about a month ahead instead of a few days.