Macbook not sending pictures in IMessage anymore

Here’s how i fixed it.

1. Sign out from iMessage
2. Finder, Go > Library (Hold option)
3. Locate Messages folder
4. delete everything ends with .db
5. restart the computer
6. open iMessage and sign in again

Hopefully they fix this issue soon :-/

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!

I followed @pungme advice, and it worked! Thank you @pungme. This worked after 2 years of not being able to send photos through iMessage and trying to figure out how to fix! I didn't understand what Go>Library (hold option) meant at first. For those of you who are also confused by this, When you're in Finder, select the GO pulldown menu at the top while holding down the OPTION key. After you find the messages folder drag anything with .db to the trash (I couldn't manually delete). You'll have to scroll through the folders--they are in alphabetical order--until you find the messages folder. Double click to open and then drag those files with .db in them to the trash WARNING--this will delete all of the message on your laptop, but they should still be on your phone. It's so nice to have this finally working. I don't think it's worked since I got my computer.

I am amazed to find that this problem definitely seems to only happen if the image is on an external drive. I have tried to reproduce this multiple times and find that every single time, dragging the image to my boot volume always works.

I have reported this to Apple through the developer feedback and included the URL to this discussion. Maybe they'll see this error and how shockingly widespread it is.

People, please STOP deleting the afore mentioned file(s)! Again, DO NOT DO THIS:

(I am only showing these steps for reference)

1. Sign out from iMessage (NOT NECESSARY)
2. Finder, Go > Library (Hold option) NOT NECESSARY
3. Locate Messages folder NOT NECESSARY
4. delete everything ends with .db REALLY NOT NECESSARY
5. restart the computer SOMETIMES NECESSARY
6. open iMessage and sign in again (DON'T SIGN OUT OF IMESSAGE)

AGAIN, DO NOT DO THE ABOVE STEPS!

Doing this deletes all imessage strings on your computer. Restarting creates a new set of .db files and they will be empty. The message strings will still be in the cloud, or on your other devices, but why bother with the frustration!

All you need do, until Apple fixes the problem, is: (as stated in my previous post)

1. Export your images/videos to a familiar location, such as to your desktop, or to a file on your desktop (mine is named "pictures for sharing") You will be asked what quality you want them to be.
2. Go to the location and open/select 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.

There is no need to sign out of ANYTHING, no need to delete ANYTHING! There is nothing wrong with your computers.

Hope this helps y'all!

I did not follow the "create a new user" advice. As you said, it sounded too extreme and a bit risky. I am just ignoring it for now and hoping they will fix the problem in a future update. I think my only issue is sharing a photo in Photos through iMessage (i.e. the "handoff" between Photos and iMessage). If you paste a photo into an iMessage message directly, it sends fine. I think it's definitely a Mac OS bug...

I am now able to send pictures via IMessage on my Macbook now. Periodically it stops and when it does, I go into IMessage on my Macbook and sign out and then sign back in and it works again. That's what works for me right now...

Have you tried or checked either of the following?

• Making sure iMessage has access to your photos and or camera.
• Disassociating your Apple ID from your computer then re-adding it
• You could also try signing into another account and see if you are running into the same issue.

I tried the 'sign-out" and "sign-in" method and NO GO....did not fix the issue.

MacOS Catalina 10.15.2

What did work though; moving the jpg images from an external drive to the internal drive. This idea is discussed in this thread.

Right now it seems if you try to drag a jpg file from an external drive to the iMessage app does not work, but from the internal drive does work.

This is random but fixed my issue finally!!!

• Launch Keychain Access (Launchpad > Keychain Access) then click File and Lock Keychain “Login” and then again go to File > Unlock Keychain “Login”, enter your admin password when you are asked. This will rebuild your Keychain Access which may fix this problem.

Raydegroat, May I ask if the image you are trying to send via the Messages app is on a internal drive to the MB? Or is it on an external drive connected via a USB port?

For me; 100% of the time if the image is on one of my external drives connected via one of the USB ports, It will not send when I try to attach it to a Message.

However, if I move that image to my desktop (the internal drive on my MBP) it always sends, never fails. I have a folder on my desktop and I transfer the image from my external drive before putting it into the message.

This is a TOTAL pain in the ***, but it works.

I'd be curious if that works for you.

Steve

This is what I have found:

This issue happens when I try to attach an image to a text message; if that image is on one of my external drives (connected via a USB port) it fails to send, always.

However,

If that image resides on the internal drive it always sends.

If the images you are trying to attach to the text are on a external drive, try moving those images to a folder on the internal drive. Then attach the image to your text and see if it sends.

Obviously this is not a solution to Apples weird issue, but it allows me to send text messages with images.

Good luck.

When I updated to Big Sur I tried to send a text with a attached image (image was on an external drive) and it worked. I posted this result on this thread.

I thought Apple had resolved this issue. Nope!

Starting about 2 weeks ago the same issue started again. If I send a text and the image I want to send is stored on a external drive, the test message will fail to send.

However, if the image I want to send (via text) is stored on my internal HD, it sends every time.

To find out if it's system wide or user specific, try this...

Open System Preferences>Users & Groups, unlock the lock, click on the little plus icon, make a new admin account, log out & into the new account.

Does it work in the new account?

For a week now I have moved my images to the internal drive before putting them into a text message. And it works.

If I try to pull an image from an external drive....Nope, it hangs up.

I would hope that Apple will figure this out, but for now; I put the images into a folder on the desktop before attaching to a text.

They'll get it fixed, come on Apple.