iMessage not sending files from my external hard drive.

Hello everyone. I had recently upgraded my MacBook Pro 15 Inch (Mid 2015) to the new MacBook Pro 16 Inch (2019). I use my MacBook for work and would send files from my external hard drive (WAV files) through iMessage. Ever since I got the new MBP, my messages would not deliver. I had found a workaround for this (Copy and Pasting to my desktop then send). Is there a reason for this? Is my hard drive not giving iMessage permission to use the files stored there?

Thank you for taking the time to read and help!

MacBook Pro 16", macOS 10.15

Posted on Jan 9, 2020 8:17 PM

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47 replies

May 11, 2020 11:34 PM in response to Castle_

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.

Jul 20, 2020 4:15 PM in response to Scott Immerman

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.

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iMessage not sending files from my external hard drive.