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 will not Allow Attachments

Since "upgrading" to Catalina, I can no longer attach files (jpeg, tiff, well, anything) to either my emails (via outloook) or messages (via imessage).


Please help.

iMac with Retina 5K display, macOS 10.13

Posted on Feb 5, 2020 6:44 AM

Reply
Question marked as Top-ranking reply

Posted on Feb 5, 2020 7:28 AM

MisterOtis wrote:

Since "upgrading" to Catalina, I can no longer attach files (jpeg, tiff, well, anything) to either my emails (via outloook) or messages (via imessage).

Please help.


Rebooting once or twice is a good first step.


To trouble shoot further you can:


Try a SafeBoot https://support.apple.com/en-us/HT201262

Takes noticeable longer to get to the login screen, does a 5-15 minute disk repair before it fully boots up, and certain system caches get cleared and rebuilt, including dynamic loader cache, etc. Login and test. Reboot and test will take a little longer as caches get rebuilt.

This test will tell you if third party interference; extensions etc are not loaded in safe boot mode.


Test issue in another user (or guest user) account  https://support.apple.com/en-us/HT204443

This will tell you if it a universal issue or isolated to your user/admin account. 



You can also reapply the combo update on top of your existing macOS to sort anomalies:

Combo update macOS 10.15.3 https://support.apple.com/kb/DL2030


Similar questions

2 replies
Question marked as Top-ranking reply

Feb 5, 2020 7:28 AM in response to MisterOtis

MisterOtis wrote:

Since "upgrading" to Catalina, I can no longer attach files (jpeg, tiff, well, anything) to either my emails (via outloook) or messages (via imessage).

Please help.


Rebooting once or twice is a good first step.


To trouble shoot further you can:


Try a SafeBoot https://support.apple.com/en-us/HT201262

Takes noticeable longer to get to the login screen, does a 5-15 minute disk repair before it fully boots up, and certain system caches get cleared and rebuilt, including dynamic loader cache, etc. Login and test. Reboot and test will take a little longer as caches get rebuilt.

This test will tell you if third party interference; extensions etc are not loaded in safe boot mode.


Test issue in another user (or guest user) account  https://support.apple.com/en-us/HT204443

This will tell you if it a universal issue or isolated to your user/admin account. 



You can also reapply the combo update on top of your existing macOS to sort anomalies:

Combo update macOS 10.15.3 https://support.apple.com/kb/DL2030


Catalina will not Allow Attachments

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