Macbook not sending pictures in IMessage anymore

If you use preview and take a selection shot of your photo, hit copy and paste into message that works until it is fixed.

I just want to say that there is a fix for this issue, but you do need to call Apple Support and talk with a senior advisor. They will walk you through the fix. I had been having the issue since November, just got off the phone with a senior advisor and she helped me resolve the issue. I am now sending messages from my MBP again.

Only solution, and it's really not that complicated:

There is absolutely no need to have your computer checked, sign out of anything, disassociate from anything, etc. Don't waste your time. Apple will eventually fix it. Until then:

1. Export your images to your desktop, or to a file on your desktop (mine is named "pictures for sharing")
2. Open the file/files.
3. Click on the "share" icon near the top of the finder window.
4. Choose how you want to share, and who to share with.
5. Delete the photos or videos when done, to avoid having duplicates.

Hope this helps.

I found that Deleting the .db files in the Messages Folder does work however you need to find the right folder (There are multiple ones)

Go to Finder and search ".db" in the search bar for "This Mac"

scroll down, select, and delete the files:

chat.importbackup.db-wal

chat.db

chat.db-shm

chat.db-wal

chat.importbackup.db

chat.importbackup.db-shm

prewarm.db-wal

prewarm.db

prewarm.db-shm

It seems this "Messages" folder is located in a hidden "Library" folder.

Once deleted the messages and photos/etc should send through correctly!

Quite a few people here saying that moving the image file to the internal drive solved the problem. I have only been working from the internal drive and I have the same problem. The only way around the issue that I've found is to copy the image file to the desktop and then drag to Messages. Not ideal and not acceptable but perhaps ok now and again until Apple actually fix the problem.

Another suggestion was to click on the file and then use the 'Share' button on the finer window - this made no difference when I tried it.

I have been reading all different ideas, approaches and comments to this on going problem and Apple's lack of solution and for what it's worth here's mine. This isn't just about Catalina, this has been on going for what appears to be years and different OS updates, etc. One day it worked and the next day....zip! I'm still running High Sierra and my problem started in March after I downloaded pictures from my iPhone to my iMac and immediately was unable to sent pictures with instant message. i spent 3+ hours on the phone with apple, and several tech people trying everything that they could come up with and still no solution. I took my iMac in to my Mac tech's who spend a couple of days troubleshooting ...to no avail.

And all of this is using just the internal drive, none of this external drive stuff.

What I have tried that worked is I created a guest user account and under this account it WORKS! But using it this way is very inconvienent and besides IT SHOULD WORK THE WAY IT"S supposed TO! ....Not with all of these work arounds, etc...

Now I'm not an engineer, but working as an electrician I know that if I go on a trouble call for an electrical problem, I'm given the background to what happened, when did it stop working, what are the symptoms, etc.. and from that I can narrow down the issue to where the problem is! WHY CAN"T APPLE? And I do not believe that they are unaware of the issue, it should be something simple enough for the people who designed the software....I don't get it, what gives?

NCP10, Since you did not say what version of macOS you're using I don't know if this will work.

This issue has been a topic for almost 2 years.

The work-a-round, for me and many others, was to make sure the image (you want to attach to the message) is not on an external drive. The image needs to be on the internal Macintosh HD drive. Once I figured this out (about a year ago) I do not have an issue attaching images to messages. If I forget and attach an image from one of my external drives...It fails to send, every time. Very annoying.

However, with the release of macOS Big Sur that issue was resolved. I updated to Big Sur and I can attach images from external drives to a text message and it sends, every time. In my opinion, Apple fixed this issue.

Good luck.

Your solution, send image from internal drive. worked for me. Thanks for posting.

Also I created a new guest user which worked fine, so why can't apple figure out why my normal user profile won't work?

Very disappointed about this bug!

The only way it woks, make a folder on the desktop, drag files into the folder, drag files out to iMessage! Having this bug since Mojave.

I wish that use of the “share” function worked for me. It doesn’t. This started when running 10.14, and while working on it with the Apple tech, they thought it would fix in 10.15, so I upgraded. No luck.

I’ve done all the sign in and sign out type activities, Now this, zero luck. It works just fine from my 2010 MacBook Air Running 10.12 (as I recall), but not my 2013 MBP. Works fine on iPhone and iPad too. Very frustrating.

I'm having same problem, unable to send pics on Mac Book Pro though iMessage. I can paste pic in iMessage and it appears to send with blue bar building across top to about 90% then it stops. I have no issues sending message with iPhone. I tried the above but no luck. Any other suggestions?

For the past month or so, I haven't been able to send photos to other Apple users through Messages on my MacBook Pro (Retina, 15-inch, Mid 2015), via a high speed WiFi connection. No problems sending the same photos using my iPhone or iPad. All devices are set to the same Apple ID. If I send the photo via the iPhone or iPad, it shows on the MacBook, and I can receive photos just fine. But when I try to send, the blue progress line gets "stuck" about 90% of the way. Eventually I just get an "Not Delivered" message.

I'm running macOS Mojave, 10.14.2, and the problem seems to date from installation of that OS.

Very frustrating.

I'm sorry, but I will not share what they helped me fix. If you don't have everything setup properly in iMessage you will lose all your conversations. I will not be responsible for that. If you call support (don't bother with the chat) and ask for a senior advisor you will get a resolution. Sorry!

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.