Macbook not sending pictures in IMessage anymore

This did not work for me. The messages app was reset, and I signed in again, but I still can not send photos. This is to other iMessages users (the progress bar is blue). Very frustrating!

You forgot to mention it would delete your entire message history on the macbook.

well that is discouraging. I have yet to upgrade to Big Sur but that was one of the features i was looking forward to have been fixed

I followed this and lost all, but one conversation and that one only has the last comment made in the conversation . I have to start all over again

Sadly, I don't see any files with .db in Library/Messages.

I'm using MacOS Mojave 10.14.6 and Messages 12.0

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.

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 agree, I shouldn't have to sacrifice my past messages to use this function.

Meanwhile, if I want to share a pic from Photos, I need to copy it's name from "get info" within Photos, then do a search on Spotlight, choose show all in Finder, then option drag to Desktop, then drag from Desktop to my Messages window to send, then delete the photo from Desktop.

All my other messaging apps from other vendors work fine, just my Apple products are problematic.

I have the same issue. Running the latest Mojave on a MacBook(13-inch, Mid 2012). 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. Our solution was to switch to using Slack.

I'm glad that worked for you. I totally agree, it was driving me nuts too.

As I've stated previously on this forum, it appears the messaging App on MacOS does not like it when the image is attached from an external drive.

Once moved to the internal, it works.

I can't imagine it is that complicated to fix.

Apple? Are you listening?

2014 iMac, 32 GB RAM, 256GB SSD. Apple OS 10.15.6 (Catalina).

I have had this problem for months, as well as several others in relation to the Apple Ecosystem that ONCE UPON a TIME worked well. I've worked through all the "potential" solutions offered and in the end the best I have arrived at is having to copy the image to the desktop first, then drag it to imessage. Like others I can't pinpoint EXACTLY when this problem started, but I had noticed I couldn't send images to friends who used Samsung Phones (from both the iMac & iphone) prior to beginning to experience this issue. I have several (8) other devices, some that don't seem to experience this issue but a couple that do. In recent times I've also begun to experience issues with trying to share from the web browser directly into imessages, as well as email. Neither now works as it did.

In my opinion the "Ecosystem" aspect of my "Apple Experience" is rapidly falling apart at the seams. I now have more reasons to leave than stay. I've already started that process by getting rid of my Macbook Pro and moving to a Lenovo replacement for it. This saved me $2000 against the "equivalent" current Macbook Pro. The same will happen for every other Apple device as it fails or is made defunct by their "forced obselescence". I rang Apple at the start of this year and told them that they'd finally lost a 12 year customer who'd spent 10's of thousands of dollars with them because their itunes store STILL to this day can't discriminate between what's been purchased years ago and the content that had one failed credit card transaction; a problem users have been complaining about for years, so I don't hold out any hope for the more obscure issues like this one. I told them I won't spend another cent with the company and have been voting with my wallet ever since. That's the ONLY language Apple will listen to now. RIP Steve Jobs, that's the day Apple Ecosystem started to die.

Without rereading all the pages, have you tried this??

Safe Boot, (holding Shift key down at startup), does the problem occur in Safe Mode?

Safe mode attempts to repair Disks & clears lots of caches & loads safe Drivers, & prevents loading of 3rd party extensions, so if Safe Mode works try again in regular boot.

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?