Macbook not sending pictures in IMessage anymore

This issue started for me too - very recently. I can send no issue via iPhone or iPad but not from my iMac. I have changed nothing that would warrant this to start. I do have automatic updates on - which if iOS was updated - then this is an Apple software bug. Do we really have to create a new user account? That sounds a bit extreme.

I think I've isolated the issue so I can duplicate the behavior, though I haven't found a solution. The problem seems only to happen when I try to send a picture along with some text. If I send just the pic, it seems to work. It's definitely an OSX problem, and is connected to a fairly recent update. Oh, and the problem seems limited to when the recipient is not using an iPhone with iMessage (green bubbles).

I hate typing messages on my phone & have found Handoff (when it works as it should) to be one of the most useful

things about iCloud & the Apple 'ecosystem'. The Messages app however is one app I hate as much as I love... the inability to perform simple tasks like bulk-message deletions or Apple's inability to fix the synchronization problem (how the messages in OSX stick around even after you delete them on your iPhone or iPad) continue to be sources of great frustration.

I too am holding out hope that Apple will fix the picture messaging bug, so I'll hold off on making any radical updates that involve creating new user accounts, etc.

Lost messages can be recovered by restoring them from a Time Machine backup. Just pick a date/time prior to when you deleted the database files. If deleting the db files didn't solve the problem, there's no harm in restoring them!

In my case, deleting the db files did not help. The image files are on the startup disk, and sharing from within Preview or Photos also fails. It doesn't matter whether I'm sending to an iPhone or an Android phone. The problem cropped up many months after installing Mojave, so if it's the OS, it's something in one of the updates.

Odd that this happens seemingly at random, to only a fraction of Mac users, even some with brand-new systems. That suggests to me that here's something being set or installed by these users that borks Messages.

I'd be curious to know if people with this issue have FileVault encryption turned on - that's a potential factor. Another possible factor is the iPhone being used, since the Messages app on the Mac actually uses the iPhone to do the sending. Mine's an iPhone 7, with iOS kept up-to-date. And who knows what combination of Mac OS, iOS, and iMessages settings (on the Mac and on the phone) might be the culprit? There are more permutations than there are affected users!

Unfortunately the only sure answer I've found is to move from Apple laptops to Microsoft laptops. Apple can not explain or fix the problem. It happens randomly and since a relatively small percentage of MacBook owners are affected, the problem remains unaddressed for well over a year now. I've had the problem on both older and newly purchased MacBooks as well as on Mohave and Catalina level operating systems. It has persisted through the three versions of iPhones and associated iOS I've had as well.

I have had this problem too. Support advised to use iMessages in safe boot. Which fixed it for a little while but now it is not sending it again. Very sucky, iMessage should work better than fb, whatsapp and such, not worse. This seems to be issue that bothers many user so I urge apple to fix this annoying bug.

Tried this and now all my conversations are gone. Worst of all, Messages on Mac OS still fails to send photos. The blue progress bar gets about 85% complete but never delivers the message. Regular text has no problems. My iPhone with has no problems using the same Apple ID. Apple never resolved this issue. Either they couldn't resolve the issue or they actually don't even know about it. It's not even on their radar.

I appears this issue was addressed in Big Sur.

I was able to send a text message with an image where the image resided on one of my external drives.

I sent several text messages to friends with pictures and all went through.

Finally!

I had this problem with my 2011 iMac running High Sierra - none of the usual solutions worked, but the problem somehow went away by itself after a few months. (Deleting all conversations did work, but only for a day or two.)

I recently got a 2018 Mini, installed Big Sur, and migrated all of my stuff to the new machine -- and the problem is back! Hard to believe there's a bug in every Mac OS since High Sierra. It's a problem that CAN be solved, but nobody seems to have figure out what the heck the issue is, or what to do about it.

I have the same issue. It used to work, and now it does not. The blue bar makes it 75% and then quits regardless of the type of wifi I am using. VERY frustrating.

Can you share with the Community what they told you to do to resolve it? Why should everyone have to track down a "senior advisor"? Thanks...

This problem has been know to Apple for months and is still not fixed.

I don't like using WhatsApp, but it works; Apple really need to look into this or offer a sensible work around.

I did a spotlight search (command+space Bar) to find the folder. I could not find the folder the way he described it either ... I fount the files and deleted them and now its working

You need to hold the option key before going to 'Go'.

I have a similar problem. When I send a pic through Messages from my MBP (Mojave 10.14.2) it seems to send, the Messages thread shows the image. But the person trying to receive it on their iphone gets only a "Downloading" message with the filename and size, but it never progresses. I see the same in the Messages thread on my iphone.

I tried signing out of Messages both on my phone and MBP, then re-signing in on the phone first then MBP.

Frustrating.

When I try to send picture through iMessage in photos app t

he picture doesn't show up in messages but a not delivered message shows up along with an icon with the jpeg # of the picture. Sometimes one picture will go through.