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Comment by jawilson2 | Hacker News Reader

Take a picture of my son's printed basketball calendar and add it to my shared iCloud family calendar. Apple/Siri couldn't do it, Claude couldn't do it. Things STILL can't talk to each other, seemingly intentionally. My wife and tried over the summer. I told her Claude+Siri could do this in 30s, and she would try by hand. 20 minutes later she was done adding each event manually, and I still couldn't get beyond trying to convince Calendar on my iPhone to open an ics or whatever file. I was supposed to open the file from Apple Mail, which I don't use, and email it from gmail or something.

This example should be "Super Friendly AI Assistant!!" and it fails on the absolute most basic thing I could throw at it.

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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.

If you had done this on a Mac, it would have worked just fine. The failure in your chain is iOS Calendar not being an intent handler for ICS files.

Another way you could have solved it would be to have the Google Workspace connection set up in the backend for Claude and it would write the parsed events to your account directly. Then in iOS you could move the events to the iCloud Family Calendar.

Or again, if you did this on a Real Computer, you could bulk-move them.

Yes, I know all of this. I have a Mac, and a PC, and an Arch Linux desktop, and an iPhone. None of the solutions are "easy." The task was "take a picture of a printed calendar with my phone and get it in my Apple Calendar (with zero intermediate steps)." This is not possible.

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