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

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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


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Catalina will not Allow Attachments

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