Macbook not sending pictures in IMessage anymore

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.

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!

Creating a new User Account (and deleting my old User) solved this issue for me.

***IMPORTANT NOTE: you will lose your conversations and User Home Folder files if you do not back them up or move them***

Create a new User by going to [System Preferences > Users & Groups]. You will need to have Admin privileges on your current User. Click the padlock image in the bottom left corner of the window and enter your User password to unlock it (if it is not unlocked already). Now click the [+] icon just above the padlock to add a new User. Select Administrator for the New Account privileges, and fill in fields for 'Full Name', 'Account Name' (Account Name may autofill), Password (you can use your current User password if you like), Verify, and Hint (optional). You will need to REMEMBER THESE DETAILS, as this will become your User profile.

Once you have made the new User, Log Out of your current User by clicking the top left of your screen [ > Log Out user name]. Now, Login to the new User you created, by clicking the icon for the User and entering the password you just made. Open Messages and login with your Apple ID and corresponding password. Your computer may ask you to confirm a 6-digit PIN (which will be sent to the computer or possibly the iPhone connected to the Apple ID). Once you login with your Apple ID, try sending a picture to yourself. Hopefully it works! If not, sorry, you will have to look for another fix.

Now, Log Out again [ > Log Out user name], and Login to your previous User. Back-up all files/photos/conversations/etc. that you want to keep onto another hard drive and/or make duplicates of the files, placing them into a new folder location viewable by the other User profiles on your mac [Macintosh HD > Users > Shared > new folder name]. Doing a full back-up is safer.

Log Out and Login again to the new User you have created. If you have duplicated files and moved them to the [Macintosh HD > Users > Shared > new folder name] path, check that you can access and use all the files (if you inadvertently created an Alias for the file instead of moving the actual file to this new folder, you will not be able to access it with your new User).

Optionally, once you have carefully MADE SURE that all of your files are accessible to your new User, you can choose to delete your previous User. Go to [System Preferences > Users & Groups], unlock the padlock again, enter your User password, select your previous User and click [–]. You will now be prompted select what to do with the Home Folder for your previous User Account. If you want to be extra safe, select [Save the home folder as a disk image] or [Don't change the home folder] (either will allow you to still recover the files in case you haven't backed them up). If you are 100% sure all your files/photos/conversations/etc. are accessible to your new User, you can select [Delete the home folder] and this will permanently delete the previous User and all files in their Home Folder.

Hope this helps!

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.

Tried this, to no avail. Signed out of Messages and iMessage (laptop and phone), I can see the Library folder with or without holding Option down, can find the Messages folder, there are no .db files in it. I'm so tired of this problem! It's amazing to me how often I want to send images through Messages. So now I have to send the images to my iPhone and send from there. Really frustrating.

My apologies, I did not understand the hold Option instructions, was navigating to the Library folder rather than using the Go menu option. I've now followed the instructions as written and it did indeed work! I have lost all my message history in Messages on my laptop, not quite sure how I feel about that but maybe I need to be better at housekeeping anyway. Thank you @pungme.

Same issue here. On both my iMac and MacBook Air both running Mojave.

I have tried all the solutions listed here, with the exception of nuking the entire user.

Any other suggestions? Super frustrating.

I am getting this problem too, although seems intermittent. I just spent 40 minutes on the phone with Apple and couldn't solve it, although not a senior advisor. My guy suggested waiting for the next Mac update to hopefully fix it. I refuse to create a new user account. Pasting a photo into iMessage instead of using Share menu from Photos seems to work more often.

Since I use my iCloud photos folder on my computer to send pictures (by either copying or pasting or clicking the upload icon) via iMessage, I would not choose to copy the pictures to another location. I like the option of always using the iCloud photos as they are always current and I don't have to do anything to have them update.

I do not mind signing out of iMessage and signing back in. This always works for me. I also don't think there is anything wrong with my Macbook. I think this occurs when I am switching back and forth with different wifi connections, such as home, work, hotels, etc. Sometimes a restart is also necessary when I have switched to a different wifi but not always.

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.

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!

I did the delete, and lost all my chats... I might not have minded, but the problem is still there.

Why isn't anyone in Apple addressing this known problem?

For me it is unacceptable (unless there is a seriously good reason, that has not yet been given) that WhatsApp functions perfectly on my Apple MacPro, yet Apple's own application does not.

Click on finder...up at the top of the screen you will see Go. Click there then hold down the option button you your keyboard. It will cause the list to show a Messages folder. Took me awhile to figure it out too.