Macbook not sending pictures in IMessage anymore

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!

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.

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 :-/

Quote: “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 :-/“

so this approach causes you to lose all message archives?? Is there any way to restore files or conversations?

Your Mac can receive and send SMS and MMS text messages through your iPhone when you set up text message forwarding. For example, if a friend sends you a text message from a phone other than iPhone, the message appears on your Mac and iPhone in Messages.

Note: To receive and send SMS and MMS messages on your Mac, your iPhone must have iOS 8.1 or later, and your iPhone and Mac must be signed into iMessage using the same Apple ID. Additionally, you must set up your iPhone.

Set up SMS and MMS messaging

Use this feature with any Mac, iPhone, iPad, or iPod touch that meets the Continuity system requirements. Make sure that your devices are set up as follows:

• Each device is signed in to iCloud with the same Apple ID.
• On iPhone, go to Settings > Messages > Send & Receive. Make sure that the Apple ID at the top of the screen is the same Apple ID that you're using for iMessage on your other devices. Add a check to your phone number and email address, so that you can be reached by iMessage at both. Do the same on your iPad or iPod touch.
• On iPhone, go to Settings > Messages > Text Message Forwarding, then choose which devices to allow to send and receive text messages from this iPhone. If you're not using two-factor authentication for your Apple ID, a verification code appears on each of your other devices: enter that code on your iPhone.
• On Mac, open Messages, then choose Messages > Preferences. Click Accounts, then select your iMessage account. Make sure that the Apple ID shown here is the same Apple ID that you're using on your other devices. Add a check to your phone number and email address.

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?

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.

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 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...

I have had this problem since upgrading my 2014 iMac to macOS Catalina. I didn't pursue it any further, because I knew I would be purchasing a new 2019 iMac.

I had finally finished setting up the new iMac and was disappointed to see the exact same problem occur.

I contacted Apple support and he had me do numerous things to include deleting the DB files.

I know that there have been some major file permissions changes with the new macOS. I have all of my photos on an external photos hard drive. When exporting, I also export to a folder on that drive.

I decided to export a jpg to the downloads folder on the internal drive of my iMac.

I can now message and send a jpg from my iMac ONLY if I am messaging a photo located on the internal drive. It's not a perfect fix, but it's better than nothing.

As indicated by user, "pungme," the solution involves Library folders. I inadvertently found the solution in another support thread. The problem has something to do with Messages not properly using the "file transfer" protocol/system.

The solution from "pungme" is not as comprehensive as the one I used, which you can find here: https://discussions.apple.com/thread/8234136?page=1. It should be the first answer served by Apple Support from user "NovaProd."

This solved months of frustration and confusion. As noted in other replies -- YOU WILL LOSE THE TEXTS THAT ARE ALREADY IN MESSAGES, even if you have iCloud sync set up. Mine have not repopulated on my Mac, but they're still all on my iPhone. I mention this in case you don't have another Apple device except your Mac.

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.

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.

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.