iMessage not sending files from my external hard drive.

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 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.

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.

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.

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

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!

Same problem here, very frustrating! I’ve always sent files via external drive to iMessage. I do not store my photos on The Apple photo app, only ones taken with my iPhone. Sincerely hope this issue is corrected soon.

I am experiencing the same issue on my iMac. If I drag a photo from my external drive into Messages, I get a "not delivered" message. If I copy it onto my desktop and then drag it into Messages, it works.

Add me to the list! Bizarre problem. Permissions all look good. ~600KB JPEG (JPG) images on my external USB3 Hard Drive (formatted as APFS) always fail to send through Messages. The thin blue progress bar at the top moves slowly and eventually gets stuck. After a few minutes I get the message that the message Failed to Send and the dreaded red exclamation icon appears next to the image thumbnail on the messages window.

Annoying workaround: If I copy the image file to my MBP's internal SSD drive the image gets sent immediately, no problem.

I tried to find some relevant message in the console but it's hard to tell what's relevant, or if there's something useful there.

Apple MacOS Catalina devs, please take a look. I can consistently reproduce this with my external hard drive.

the best thing about i-message is that I can use it from muliple devices. if this doesn't work we migvht as well give up on imessage and start using whatsapp/whatsapp desktop. (which degrades image quality)

NOT COOL APPLE! please fix this!!

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)

Same problem also I guess ANY person with an external disk has the same issue.

How hard can it be to solve something like this the use to work fine and just suddenly stopped ?

Solutions like reinstall MacOS is not a solution its a massive problem for people that use their Mac for work.

Its like suggesting buying a new car because the tire is flat....come one Apple you can find a solution to this

and make our work life easier , basically how it used to work nothing more than that...

You're right, mate. Just did it.

Besides of that, I'm sure Apple knows very well about this soooo annoying issue, it just isn't a priority for them. I have no other explanation why they even don't bother to respond here with some BS like "We are investing on this, stay tuned..."

But Apple isn't the same company as we know it from the Steve J times... this is what happens when tech companies are run by accountants and marketing cuties instead of clever people, who burns with technology and strives for tech. excellence and perfection. Sad times...

Same here – although I can't send ANY file from ANY location (internal or external hard drives, flash drives, whatsoever). And it doesn't matter the size of the file: tried to send a 50MB PDF to my girlfriend, didn't send; tried to send a 4MB HEIC image, didn't send; tried to send a 10KB PDF, didn't send. Awful.

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.