iMessage not sending files from my external hard drive.

Have the exact same issue. Had it since updating to Catalina. Has not been fixed per 10.15.4. This is critical as many users has external drives connected, especially for media. Lots of clients expect to get smaller files through messages. Incredible that Apple refuses to fix a pretty critical issue.

Support is awful these days. I had a rude response with a faulty explanation that I had 3rd party apps installed such as photoshop. Complete nonsense. I do t think Apple realize how much their brand is being hurt by the Current poor Software development and customer service. Eventually we will move on to another more reliable product.

It would be great if Apple took this issue seriously and fixed the issue. It is critical for pro users as we have external drives with media and clients expect to be able to communicate through messages.

I have the same problem. Any attempt to send a photo or video file from iMac via iMessage fails to go through. Even in the Photos App, I can click the box with up arrow icon, choose Messages, and it will fail. The recipient gets a downloading icon, but nothing goes through. Please fix!

Still happening its been happening for a while , "make a new account" was the only suggestion I got from customer service , which did not work. Even if it did, you can't fix the imesssage problem by putting your customers migrating all their files and settings to a new account? That's just not practical or logical.

The crazy thing is that it USED to work perfectly on any file from any location , how can Apple break something that works and then don't have the solution or at least being able to roll back whatever internal MacOS problem is causing this.

When you advertise iMessage as the best messaging service but you can use it for nothing else than text from your computer its just plain wrong...

A few months or years down the line from now if all these little issues (there are more) don't get resolved there is no point for people paying the premium super high prices Apple demands for the Apple ecosystem.

I would recommend that anybody having this issue go directly to apple‘s feedback site, and specifically choose macOS and iMessage, submit this as a bug report like I have, and the more people who do so may have an impact on getting a fix. They know of the issue and I am a bit confused as to why they haven’t fixed it, even with this most recent update.

It is perfectly clear that they are well aware of this problem - many of us submitted their bug reports. What I find very disappointing is Apple's behavior of complete ignorance and silence - they even don't bother responding to the bug reports.

Besides that sh*tty behavior, which simply is completely wrong, it seems this isn't something easy to get fixed and this may has something to do with the new 16" MB Pro's new security architecture (Apple Watch derived chip?). Everyone that I know who is using the 16 Pro is having this problem with no exception. The previous models doesn't suffer from this "bug".

Otherwise I see no reason why this isn't fixed yet.

I wholeheartedly agree with you on the frustration, but I disagree about the hardware. This is happening to anybody using this version of macOS… I have three Macs, and two of them are from 2015… They all have the same issue as are several colleagues with IMacs.

I believe this a new ‘feature’ as messages is running under catalyst and therefore sandboxed from accessing files on external disks. If you see the timeout error in the console it’s a sandbox error.

I think this bug is here to stay if that’s the case

If that is the case, that is very unfortunate and seemingly senseless given the fact that they let you put the photos library on external drives. If it is a security feature, it would make a lot more sense to make it an optional one IMHO.

Yes. The problem is permissions. It’s clear by now how bad Catalina is, especially on larger systems. It’s fundamentally an unstable platform at this point. Crashes on start up. Issues with the latest Intel chips. Apple techs are aware and can reproduce the issue, but no fix so far. On top of if Avid systems are having to skip entire versions due to bugs on MacOS. It’s like the early 2000’s all over again.

Now we've seen the announcements from WWDC, I'm much more convinced this is actually by design and not a bug at all..the messages and other system apps are limited on their sandbox access to local disks only for security reasons.. I just setup an automator script to move the files, then add to Message... annoying but it is what it is..

Easy or not is irrelevant bits a fundamental feature of the MacOS to be able to use Messages. Not being able to drop images from an external drive is inexcusable IMO. It sadly shows that Apple no longer had the focus or resources to fix fundamental bugs in their software. I’m not leaving the platform, but Apple has been heading in the wrong direction for Pro users in the last 5 years.

To be honest, I'm not sure how Apple has had this many problems. It is very disappointing as the reason for Apple is to have a very high functioning ecosystem. The people they created Macbooks for are the ones getting slighted. After speaking to 2 different CSR's in a support chat, neither one of them had even heard of it and simply wanted to suggest that I recover my macbook.

If i can't use this feature... might as well just use Dropbox for everything. In that case, windows may be competitive. It's just a shame to see so many bugs and problems. I have had tons of problems ever since Catalina. Crashing and refusing to force quit items. Screens not syncing. Etc.

Please fix this soon Apple.

Bug report sent. Thanks for the link!

Paying link forward: https://www.apple.com/feedback/messages.html