iMessage not sending files from my external hard drive.

To be honest, I'm not sure how Apple has had this many problems. It is very disappointing as the reason for Apple is to have a very high functioning ecosystem. The people they created Macbooks for are the ones getting slighted. After speaking to 2 different CSR's in a support chat, neither one of them had even heard of it and simply wanted to suggest that I recover my macbook.

If i can't use this feature... might as well just use Dropbox for everything. In that case, windows may be competitive. It's just a shame to see so many bugs and problems. I have had tons of problems ever since Catalina. Crashing and refusing to force quit items. Screens not syncing. Etc.

Please fix this soon Apple.

Same problem here! Can't seem to send pics etc from an external drive. But, if I move it to my desktop it sends without problem.

OS 10.15.3

Lacie Rugged Raid 4TB Hard drive

I'm having the same issue here. Can someone please help us solve this???

Same problem here. Catalina 10.15.4 - attempting to send image or even files located on external drive via iMessages fails.

Me too... this must be a bug. Why is Messages sandboxed to not allow external drive access? Why can't we permit this as Security Preference??

I have the same issue with my 2019 Mac Pro with a secondary internal drive! Strangely only with my AppleID, the AppleID of my wife works fine.

Indeed it isn't! Pretty annoying!

That sounds to me like a different issue. We are talking about files being inserted from an external drive. The symptom does not leave empty download icons but rather the file simply won’t transmit.

Well, if this is the case, then the issue is certainly not hardware related - the drama hides somewhere else. Thanks for confirming, this is good to know.

Totally agree...not defending it..just speculating...

Just tried this - doesn't work. The fix isn't this easy, I think.

Yes I've already tried it! Does not work! iMessages also sends pictures from an external drive. But no Videos.

You might wanna double check that… I have not been able to get any pictures or video to send from an external drive directly via iMessage.

I'm having this issue as well. Won't send any photos via Messages from my desktop.

it doesnt.