Macbook not sending pictures in IMessage anymore

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!

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.

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.

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.

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.

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.

Nope, that did not affect the issue for me. However, the source of the image file (internal drive vs external drive) has worked consistently.

Therefore, until Apple fixes this bug.....I move my images to the internal drive before attaching to a message.

This is, perhaps, the most enraging thing I have ever encountered. And Apple should be ashamed of itself for not making this easier; however, the solution is somewhat simple. You just have to set up message forwarding on your iPhone. Apple should identify this when a user is unable to send photos. But, Tim Apple isnt the greatest

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...

Lost messages can be recovered by restoring them from a Time Machine backup. Just pick a date/time prior to when you deleted the database files. If deleting the db files didn't solve the problem, there's no harm in restoring them!

In my case, deleting the db files did not help. The image files are on the startup disk, and sharing from within Preview or Photos also fails. It doesn't matter whether I'm sending to an iPhone or an Android phone. The problem cropped up many months after installing Mojave, so if it's the OS, it's something in one of the updates.

Odd that this happens seemingly at random, to only a fraction of Mac users, even some with brand-new systems. That suggests to me that here's something being set or installed by these users that borks Messages.

I'd be curious to know if people with this issue have FileVault encryption turned on - that's a potential factor. Another possible factor is the iPhone being used, since the Messages app on the Mac actually uses the iPhone to do the sending. Mine's an iPhone 7, with iOS kept up-to-date. And who knows what combination of Mac OS, iOS, and iMessages settings (on the Mac and on the phone) might be the culprit? There are more permutations than there are affected users!

Unfortunately the only sure answer I've found is to move from Apple laptops to Microsoft laptops. Apple can not explain or fix the problem. It happens randomly and since a relatively small percentage of MacBook owners are affected, the problem remains unaddressed for well over a year now. I've had the problem on both older and newly purchased MacBooks as well as on Mohave and Catalina level operating systems. It has persisted through the three versions of iPhones and associated iOS I've had as well.

FloatingZack,

FileVault is not turned on.

iPhone XS iOS 13.4

MBP 15" 2018 macOS Catalina 10.15.4

This really is a PITA for sending images via the messaging app on my MBP. I can not say when the issue started (which update) but I can tell you; If I move the image to the internal Mac HD the images sends every time, never fails.

If the image is on one of my external drives via USB, it never sends, ever. I have been using this procedure for several months now and it is the only way I can attach an image to a text message.

I agree that it is probably a settings issue. I have brought it up to Apple twice and they have no idea what I'm talking about.

Yes, it bugs the crap out of me, but not enough to sell my MBP and buy a Windows platform.