Messages on iMac with Catalina no longer sends files

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Level 1

8 points

Messages on iMac with Catalina no longer sends files

I recently upgraded to Catalina and I was using the Messages app with no issues. It would send texts and files like normal. Then about a 4 or 5 days ago, it would no longer send files, no matter what type. I've tried almost all the things I can find on the internet about logging in and out of my accounts on my iMac and iPhone, deleting .db files from the Library and from other locations (which requires a restart on the computer). I don't know what to do as I've changed nothing and it has just stopped being able to send files. I can still send texts normally, even to SMS and group chats.

When I do try to send a file, it immediately pops up as failed to deliver. If I try to send it to myself (my iPhone number), it hangs on the upload line at the top of the window at about 90% or so and never finishes.

Any ideas on what I can do to try to remedy this?

iMac 27", macOS 10.15

Posted on Oct 30, 2019 3:49 PM

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Answer 1

Top-ranking reply

i_rina

Community Specialist

Nov 5, 2019 6:53 AM in response to Buddymas

Hello and welcome to Apple Support Communities, Buddymas.

If I understand your post correctly, you're unable to send files via text message in macOS Catalina. I'd like to help.

Let's do some testing to narrow down the issue.

Safe mode will tell us if the issue is related to a startup item or plugins, and sometimes corrects the issue. This article will tell you how: Use safe mode to isolate issues with your Mac

If everything is working correctly in safe mode, but is not working when you get back to your user account, please check the section titled "If an issue doesn't happen in safe mode" for the next troubleshooting steps.

If the issue continues while in safe mode, a test user will let us know if the issue is isolated to your account, or system wide: How to test an issue in another user account on your Mac. If the issue happens in the test user also, then please check the section titled "If an issue happens in more than one user account."

If the issue continues, let us know the results of each of these tests.

Thanks for using the Apple Support Communities. Take care.

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Answer 2

Buddymas Author

Level 1

8 points

Nov 5, 2019 2:26 PM in response to i_rina

Thank you so much! That worked. I booted my iMac into Safe Mode, tried to send a photo in Messages and it worked. I rebooted to the standard operating side and tried it again and it worked. Very grateful!

Budmas

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Messages on iMac with Catalina no longer sends files

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