Macbook not sending pictures in IMessage anymore

I see everything up to #3, but I don't see anything inside the messages folder that ends in .db. There isn't much in there at all. Any other ideas? Or do you know why I don't see messages inside the folder?

I totally agree. I have a partitioned hard drive with maverick on one, and High Sierra on the other. IM was working on both systems fine until I downloaded a bunch of pictures in March and tried to send a picture on IM in High Sierra to myself or others....I get file transfer message " Waiting for me to accept " and it never sends/goes through. I spend 4hrs on the phone with an apple supervisor and got no place....Very frustrating! Seems to me one should be able to give the experts a list of symptoms and they should be able to diagnose the area that's causing the problem. But Apple pretends there's no issue or just upgrade, etc...My old Maverick OS works perfect!...I can send pictures from my iPhone, but not from my iMac ...This is so wrong and EVEN if some of the solutions suggested here worked ( Which they haven't for me! ) I shouldn't have to go through all of this. Apple never wants to admit an issue or gives me an answer " We are working on it" APPLE...FIX YOUR PRODUCT!

This worked! After weeks of hunting down a solution! I would note that messages on my computer are cleared out, like a full reboot back to day one...I guess the good news is they are all still on my phone. Either way, happy with the solve! Thanks pungme!!

Thank you! This fixed it for me. I wish Apple would fix bugs that linger for more than a year and affect many of their most loyal customers. But they seem to get ignored if they aren't reported by a very vocal majority of users (see also: FaceTime WiFi iOS bug).

I was okay with losing my local message archives on my iMac, since they're still in iCloud, on my iPhone etc.

That said, if you are backing up Messages to iCloud, there's an option in Messages Preferences on the Mac to "sync now" which I would expect to restore the archives. I can't say for sure because I did not do the sync. I was concerned that re-syncing would re-introduce the issue.

I've tried most of the suggestions on this discussion site. I've spent hours on the phone with Apple technicians. Perhaps something that most of us, including Apple technicians, tend to forget when one of these miracle workarounds helps is that the problem is often intermittent and recurring. So just because it doesn't happen now, doesn't mean it won't happen again. If anyone has an idea on how to catch Apple's attention so that they fix the problem, it'd be helpful if you shared.

They aren't. This fixed it for me as well. It is a PITA to copy-> then upload.

I had simialr but opposite issuse with Photoshop on Mojave. I couldnt edit files on the local drive, but could if they were on a mounted one

Those are steps that we already use, and are set in place. The problem is iMessage had its own mind, decided to stop sending out images when it was working previously without any problem. What is the next step to get this fixed? Who can I contact with to get this thing fixed? It is interfering my business, having to find other way around to send images to customers, which is time consuming.

Thanks!

Ok, I set up a new user account and it works under the new account.....So now what do I do?

and

Why is it one day this was working and now the only way it works is through another user account?

My admin account ( which I never run ) and my normal user account both have this problem.

Thx

Sorry, But as I mentioned in an earlier post, I'm ONLY using an internal drive. And no one should have to go through all of these work arounds anyway....It is suppose to work as advertised! This is not a mojave problem, nor a catalina problem, nor a high sierra problem....this has not been working right for a long time, It's an APPLE problem that they refuse to acknowledge ....

thx anyway for the suggestion

Send your message with your wallet (or lack thereof) in the future. That's the ONLY message they're going to take any notice of anymore. I'd spent close to $50K over approx 12 years with Apple and I'm walking away now piece by piece. Their "Ecosystem" is no longer unique, doesn't work as advertised, in fact it's falling apart before our eyes. There are perfectly good alternatives now for EVERYTHING that pulled me over from Windows 12 years ago. Apple TV, expensive junk now. MacBooks expensive aluminium cans. iMacs barely a skeleton of their ancestors, in fact much less useful after losing targeted display for no good reason. Operating system and updates, buggier and buggier by the year. If you have an iPhone, get rid of it and the rest will follow. Once you recognise that it's the only thing tying you down to the Ecosystem you'll be free of expensive upgrades every few years.

I've about had it w/ Apple now. Windows 10 certainly works very well now. Between something so basic as being able to send images and I'm guessing most everyone using a Mac now has this problem and it's been present FOR YEARS now. Between this, and losing the wonderful MagSafe connector, I have lost the desire to buy another MacBook Pro, and I'm on my 2nd one now. I bought #2 in order to get the last year MagSafe was happening. No more they've lost there way.

Thanks for the confirmation.

I wanted to send another update that now, after deleting the DB files, image messages I send go through to the person I am messaging.

HOWEVER,

now, I DO NOT receive image messages on my computer, only on my phone (I get the question mark instead of a picture), and I did used to receive them.

I may try adding the db files back to the library and deleting them 1 by 1.

this is definitely something apple should fix, esp for us running the old OS systems.

That doesn't make sense.

Tell us the solution, and we will decide whether or not we'll actually do it. No one will hold you responsible for our own decisions.

ever since I updated my MacBook to MacOS Mojave I can't send photos in my i messages . grrr. What is the solution to this issue?