Macbook not sending pictures in IMessage anymore

Finally got it figured out! Someone was saying something about external hard drive not working. I copied images from external hard drive to desktop then sent it out via sms, lo and BEHOLD it finally sent out! When I returned back to external hard drive, it will NOT send out image AT ALL!

So my temporary fix is this: copy any images that I want to send out via imessaging to desktop space then send it via SMS. It works!

Thanks!!!

Scott

I was having the same issue with my new MAC Mini. Photos would not upload in Messages.

Super frustrated. Finally I called AppleCare and the first question the tech asked me: Are the pictures on an external drive?

What? Why would that matter? But yes in fact they are - I keep all my photos on an external USB 3.0 4 Tbyte RAID 1 drive - for redundancy purposes.

Ok, please try taking the photos in question and coping to MAC Mini SSDD drive and then upload.

Sure enough that "fixed" it!

Mac OS Catalina MESSAGES won't upload pictures from external drives. You have to move them to the MAC's internal drive/ssdd first.

I'd been struggling with that issue for months. That is all it was.

I now realize why it worked on occasion. It worked with the pictures were on the SSDD - typically after having dumped them off my Iphone.

Apparently Messages can't resolve addresses to external drives.

Hope this helps someone else!!

Chris, I've been posting this solution for several months.

There have been some response's saying it worked and also, some say it does not. For me personally, it never fails. My texts (with image) always sends if that image is attached via the internal drive.

I find it interesting that a tech at AppleCare told you to move the images to the internal drive; that's a first. Glad they have recognized this issue, maybe a fix will come with the next OS updates.

Well I didn't do it in this order, because I wasn't aware of how to sign out. So I did #4 then #1, and now after I restarted all my messages on this Mac are gone. They're still on my other Mac and iPhone though.

I just clicked Sync Now and got back messages from yesterday back, but all the files now have a page icon and "i" next to them. When I click it a new window that says File Transfers pops up. It's empty.

We need to somehow make the public aware of this issue!

Glad it worked for you, but plenty of us are working from internal drives and have zero success.

S4Ducati wish I had seen your post months ago - saved me some aggravation.

Yep, it works everytime for me if I put photos on Mac Mini SSDD drive.

thanks

Curtis

Bummer this doesn’t work for everyone.

try it now if you've installed Big Sur