Macbook not sending pictures in IMessage anymore

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.

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 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.

I have had this problem and open an open case throughout 2019. It happens on both my MacBooks and on both Mojave and Catalina operating systems. It is outrageous that the only answers I have EVER gotten from Apple is that they are aware of the problem and their "engineers" are working on it. Working on this for an entire year? Oh PLEASE!

If anyone knows how to escalate this issue or to give it the public awareness it deserves, please let me know!

Thanks!

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.

Better solution:

Apple, please FIX the problem so that your devices work the way they are advertised to work.

OR, Apple, as part of your advertising to potential buyers, please include a disclaimer that texts may freeze while sending pictures and/or PDFs, and that once frozen, no additional texts to the same individual can be sent for hours on the frozen device.

These problems sending pictures and PDFs via text are intermittent. So workarounds that work and look good for a string of consecutive attempts, by definition won't work consistently.

What can be done to tell the buying public that Apple devices experience these issues and that no solution exists?

Agree that the issue seems intermittent. I've had images send at times.

I don't keep records of when it does and doesn't work to know if the source of the image was on board or external.

What I can say, is, It's working right now when the source of the images in on board.

As long as it continues to work, fine. I really don't care if Apple warns customers of all the issues with their products. I'd still buy it. The positives outweigh the negatives.

It's nice that the issue doesn't bother you when it doesn't happen on your device. And it is nice that there are some workarounds that are successful intermittently. But I don't think that we should have to go onto consumer message boards to search for potential temporary/inconsistent fixes.

I think that this is a serious product defect and is worthy of a product recall. If potential buyers were aware that the a new, expensive Apple computer may not send pictures consistently via text and that there is no support from Apple and there are no plans to resolve the problems, sales would drop.

This is a textbook example of "let the buyer beware". Bad Apple!

Well, I think I've deleted too much, because now I'm unable to sign back into iMessage entirely. Trying to fix one small problem (sending pictures,) I seem to have created a much larger one. Please help.

It has been about a year since I have been able to consistently send pictures via text on any of my laptops and/or operating systems. I hoped Apple would fix the problem also. I've made many attempts and spent many hours working with their "service" technicians trying to correct the issue. All my attempts working with Apple Support have ended in the same place with Apple saying that they are aware of the problem and their engineers are "working" on it.

My guess is that it the problem isn't widespread enough for Apple to put any real effort into fixing it. If that's true then unless pubic awareness can be raised, there isn't a reason for them to resolve the issue.

Oh Hey! 😃 ...

Here's one more enraged Apple user who is willing to go to totally unnecessary lengths to help Apple cover up an outrageous blunder and user hardship that they refuse to address publicly...

You should be wary of making statements like this - this may have worked for you but should not be considered as "the solution". Enabling message forwarding was one of the first things I did and it made no difference at all.

I keep a folder on my desktop specifically for images I want to send via text.

I will try moving that folder to the Download (or other) to confirm your experience.

This issue is really annoying, and hopefully Apple figures it out. I surely would consider moving to another platform because of this; as some others have stated, but it is annoying.