iMessage not sending files from my external hard drive.

Have you tried adding Messages to System Preferences -> Security & Privacy -> Full Disk Access ?

This may fix the issue, until it is resolved by Apple.

I just spoke to an Apple Support rep and they told me that this is a know limitation with Catalina. That sending files from an external drive is "no longer supported" (!) and that the file should be imported in other ways, such as from Photos, etc!

Frankly, I don't buy this explanation. This just smells like a BUG. I can't imagine what difference it makes that the file is located on a different path. As long as the disk/volume is mounted and the permissions are correct, there should be no technical difference in accessing the file to be sent. And if Messages can't access the file it should just report it immediately (before attempting to send it).

Even if there is, indeed, a good technical reason why files on external drives shouldn't be sent through messages, then the right thing to do is disallow any actions that attempt it. For instance, dropping the file onto the Messages window should fail immediately with a message telling the user that the image can't be sent from that external drive. Attempting to use the share menus should do the same.

Not telling the user beforehand and just letting the action fail, inexplicably, after a few minutes is very frustrating for the user and just not "The Apple Way". Besides, there's no way to figure out why it failed, even after the fact!

Here's hoping that the Messages team pays attention to this. The Apple Support Rep recommended opening an issue at https://www.apple.com/feedback/messages.html. If they get enough people reporting this maybe they'll have to acknowledge it or, better still, fix it. So if you have two spare minutes, just open that link and file a report with your feedback.

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..

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

On my system the following applies:

The desktop directory is from the internal drive, which is default for all systems, unless specified differently in System Preferences.

If the picture or video file(s) are copied from an external drive to the desktop it will still initially not send successfully. I have found the following solution to work (at least on my system).

1. Copy the file(s) from the external drive to the desktop.
2. Log out of your account.
3. Log back in which seem to refresh the permissions,
4. Send the file(s). Since the file(s) reside on the internal drive everything works as expected.

As I said above, our best bet is to open a ticket for this. If each one of use does the same, the engineering team will see that it's not just one person. So please go here and create a feedback ticket for Messages:

https://www.apple.com/feedback/messages.html

Just explain the issue that you're having with files located on external drives. It takes less than a minute.

Make sure you report the problem officially https://www.apple.com/feedback/messages.html

Indeed. No pictures or videos from any external drive It’s a known issue according to support, but sadly enough not deemed important enough to fix.

Hello Castle_,

I understand you're not able to send WAV audio files via Messages on your MacBook Pro. I recommend trying out relevant steps in this support article below. If you can’t send or receive messages on your Mac.

Reach back out if you need continued support with this.

Take care.

I have the exact same issue - I was using MB Pro 2015 and upgraded to the new 16" MB Pro. Ever since then, I'm unable to send files located on *external drives* via iMessage, regardless of the file type. When I copy the file on the local SSD (i.e. in downloads or desktop folders, etc.) it works.

I have my Lacie external SSD connected directly to one of the TB3 ports. Permissions are OK, I can read & write, but it seems iMessage thinks differently. Never ever had this problem before with any of my other Macs.

This is obviously a bug and quite an annoying one. Apple, please fix this!

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 have the same problem, only I am sending (very) small jpg's

My imac starts blowing it's fans like mad as well.

This is right after I updated to Catalina.

I updated permissions on the external drive to "everyone" no difference. Very odd.

Cheers,

Mark

Same: cannot send images using iMessage if the image is located anywhere other than the system drive. Drag image from external drive -> iMessage no dice. Drag image from Desktop -> iMessage no problem. :(

macOS 10.15.4 (Catalina)

FYI, I reported this bug months ago after Apple support told me my external hard disk was bad (LOL). They later acknowledge an issue but provided no estimate for resolution. I can't believe this is still not fixed.