Macbook not sending pictures in IMessage anymore

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.

Quite a few people here saying that moving the image file to the internal drive solved the problem. I have only been working from the internal drive and I have the same problem. The only way around the issue that I've found is to copy the image file to the desktop and then drag to Messages. Not ideal and not acceptable but perhaps ok now and again until Apple actually fix the problem.

Another suggestion was to click on the file and then use the 'Share' button on the finer window - this made no difference when I tried it.

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.

I had the same problem.

The problem was an active blacklist on my router. Here I had blocked a few Google addresses.

After I had cleaned up the list a bit, a synchronization for iCloud and iMessage (sending again images) was possible.

Is it very likely that something is going through google due to the increased data volume on the Internet?

I wish that use of the “share” function worked for me. It doesn’t. This started when running 10.14, and while working on it with the Apple tech, they thought it would fix in 10.15, so I upgraded. No luck.

I’ve done all the sign in and sign out type activities, Now this, zero luck. It works just fine from my 2010 MacBook Air Running 10.12 (as I recall), but not my 2013 MBP. Works fine on iPhone and iPad too. Very frustrating.

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 followed @pungme advice, and it worked! Thank you @pungme. This worked after 2 years of not being able to send photos through iMessage and trying to figure out how to fix! I didn't understand what Go>Library (hold option) meant at first. For those of you who are also confused by this, When you're in Finder, select the GO pulldown menu at the top while holding down the OPTION key. After you find the messages folder drag anything with .db to the trash (I couldn't manually delete). You'll have to scroll through the folders--they are in alphabetical order--until you find the messages folder. Double click to open and then drag those files with .db in them to the trash WARNING--this will delete all of the message on your laptop, but they should still be on your phone. It's so nice to have this finally working. I don't think it's worked since I got my computer.

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!!

https://macreports.com/cannot-send-or-receve-messages-on-your-mac-fix/comment-page-3/?unapproved=109815&moderation-hash=8844eb3d3f11a9b188ada09b6980845e#comment-109815

6- Your problem may be because of your date and time settings. Lets resolve this. Click Apple menu > System Preferences > and then Date & Time; select the Time Zone tab and the “Set date and time automatically” checkbox, if it is already selected, unselect and wait a few seconds and reselect again. You may need to enter the admin password if the checkbox is dimmed.

I have had this problem too. Support advised to use iMessages in safe boot. Which fixed it for a little while but now it is not sending it again. Very sucky, iMessage should work better than fb, whatsapp and such, not worse. This seems to be issue that bothers many user so I urge apple to fix this annoying bug.

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.

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.

Tried this and now all my conversations are gone. Worst of all, Messages on Mac OS still fails to send photos. 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.