You can make a difference in the Apple Support Community!

When you sign up with your Apple Account, you can provide valuable feedback to other community members by upvoting helpful replies and User Tips.

Looks like no one’s replied in a while. To start the conversation again, simply ask a new question.

Catalina now can't send attactments (small) with Messages

Using Catalina/Mac Mini - without having made any changes, Messages now won't "deliver" a text wtih an attachment (even a small file) -- this is happening when I try to send to another iMessage user or SMS. Both my iPhone (6s+) and new iPad work perfectly.


Would re-setting Messages help, and if so, how do I do that? Thank you.

Mac mini, macOS 10.15

Posted on Apr 20, 2021 7:41 AM

Reply
Question marked as Top-ranking reply

Posted on Apr 22, 2021 5:17 AM

Michael,


It shouldn't matter too much if you reboot your internet hardware before or after your Mac clean up. However, if the issue persists after rebooting your hardware we would recommend reaching out for additional support here: Get Support

4 replies

Apr 21, 2021 8:26 AM in response to MichaelJonas

Hi MichaelJonas,


We see you're having trouble getting your messages delivered from your Mac. Have you tried restarting the Messages app or your Mac to see if the issue persists? To clarify, when you're just sending words it goes through via iMessage or SMS? We would recommend restarting your Mac and internet hardware before signing out of iMessages to resolve this.


We look forward to hearing back from you.


Take care.

Apr 21, 2021 5:26 PM in response to i_rina

Thank you for the instructions. I've rebooted my Mac Mini, and once a week I clear all the caches (~libraray/caches/). reboot in Safe Mode, then reboot in regular mode. What I haven't done is reboot the router/modem...should I do that before or after my "housecleaning"?


I'm always concerned abut the order in which to do things. And if there's anything else you can suggest, I'm all ears, so to speak.


Again, much thanx.

Catalina now can't send attactments (small) with Messages

Welcome to Apple Support Community
A forum where Apple customers help each other with their products. Get started with your Apple Account.