Since latest OS and iOS updates, I often get a "not delivered" message when sending a PNG or JPEG file on my MacBook Pro and iPhone. This is a recent bug, and I've tried closing the iMessage app, syncing, converting the PNG to JPEG. Any other solutions to this?
MacBook Pro 15″, macOS 13.7
Same issue, but add .HEIC, .tiff, JEPG-2000 as not sending 'Message failure' issue.
work around is [from the finder] to click on the picture to highlight, go up to the menu bar & click on 'File' & down to 'Share...' & select Messages from the list.
OR just right-click on the picture & select 'Share...' from the drop down menu & then select 'Messages'
but then again - I do not a work around, I want to drag & drop into the messages window, directly, like I always have.
I found a solution from another Apple Community page :
Macbook not sending pictures in IMessage … - Apple Community which I am trying next. I have 'messages saved to the cloud' turned on, so nothing is lost & maybe if the database is not rebuilt automagically, then I'll just resync from the cloud & all is good again. hope this helps & works for you. Cheers!
Same, Jpegs dragged from the desktop in Tahoe end up with a "Not Delivered" message. (Mac: Studio M1 Ultra 2022-Tahoe 26.2)
The workaround mentioned works if I "share" from the jpeg by right-clicking, I suspect the feature to let others "collaborate" or "Send Copy" may be complicating a simple action that always worked in the past.
I see no use case where I would want to collaborate on a photo.
iMessage won't send a PNG or JPEG file
