iMessage not sending files from my external hard drive.

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.

Bug report sent. Thanks for the link!

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

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 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.

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.

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.

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.