macOS Catalina (10.15.7) - messages not sending attachments

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148 points

macOS Catalina (10.15.7) - messages not sending attachments

So I have macOS Catalina (10.15.7) and I have been using message to send files (images, contacts, xlsx) files. But for some reason all of a sudden I can send images and contacts but not xls files. The progress bar is 95% and then gets stuck there an times out eventually takes about 10 minutes or so.

Error: Message failed to send

Not delivered.

What I have done.

Troubleshooting 1

restarted
shutdown
try to send xlsx didn't work

Troubleshooting 2

logged out of iCloud and messages
shut down
logged back into iCloud and messages
try to send xlsx didn't work

Not sure why its not working. Any help would be appreciated.

Posted on Nov 10, 2021 2:15 AM

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Answer 1

Top-ranking reply

SU Author

Level 1

148 points

Nov 15, 2021 7:55 PM in response to SU

solution:

logout of messages and icloud
shutdown
command+option+p+r reset x3
boot up
login to iCloud and messages

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Answer 2

SU Author

Level 1

148 points

Nov 10, 2021 1:32 PM in response to PRP_53

I have a few more troubleshooting efforts since I was able to resolve it awhile back but pandemic appreciation blurs the days for awhile. I'll be sure to report back if I eventually get it resolved again.

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