Can't attach files on emails

There are two workarounds:

1) Most times dragging and dropping the file works; or

2) Re-install Mojave from Recovery which gives you Safari 12.2.1, then do the updates EXCEPT for Safari 14.0.1 and 14.0.2. You end up with Safari 14.0 which has none of these issues.

The issues seem confined to Mojave. I think it's Apple way of trying to encourage us to upgrade. First there was the kernel crashes on sleep/shutdown/wakeup only solved by doing a Big Sur install (to an external drive) to update the T2 BridgeOS. Then there is the fact that, after all that, the Crash Reporter now crashes when trying to send Apple crash reports. It's an upgrade conspiracy :-)

Hey there, Pablo35.

We understand that you're unable to attach any files in both Gmail and Hotmail. Can you tell us what happens when you try to attach a file? To confirm, this is happening in webmail for both Gmail and Hotmail in Safari, correct? Your answers can help us determine what might be going on.

If it only happens in Safari, you can try quitting Safari and trying again: Quit apps on Mac You can also see if restarting your MacBook Pro will help: Log out, sleep, restart, and shut down Mac To isolate further, you could also try in a new administrator test user on your Mac as well: Set up users, guests, and groups on Mac

Take care.