Photos to Day One – iOS / Mac Share Sheet – maximum file size?

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  matthewhsu · Member · May 6, 2025 at 11:21 am

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  I’m having an issue where sharing photos from Photos via the iOS or Mac share sheet sometimes fails. The New Entry window briefly pops up with the prompt “What’s happening?” but then immediately closes and the photo is not added to my Day One journal.

  I suspect that it may have to do with the file size? One photo that recently failed is 30MB, but 2MB files are shared with no issue. What’s weird is that importing the photo from Day One works with no problem, it’s just when I try to share from Photos.