Macbook not sending pictures in IMessage anymore

My brand new MacBook Pro is not sending pictures in iMessage. normal text no problem - all up to date.... what can i do?

has anybody found a solution for this long standing problem?

MacBook Pro TouchBar and Touch ID, iOS 12.1

Posted on Nov 27, 2018 8:00 AM

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Posted on Apr 8, 2019 6:24 AM

Here’s how i fixed it.


  1. Sign out from iMessage
  2. Finder, Go > Library (Hold option)
  3. Locate Messages folder
  4. delete everything ends with .db
  5. restart the computer
  6. open iMessage and sign in again


Hopefully they fix this issue soon :-/

174 replies

Apr 11, 2020 6:39 PM in response to jpdemers

FloatingZack,


FileVault is not turned on.

iPhone XS iOS 13.4

MBP 15" 2018 macOS Catalina 10.15.4


This really is a PITA for sending images via the messaging app on my MBP. I can not say when the issue started (which update) but I can tell you; If I move the image to the internal Mac HD the images sends every time, never fails.


If the image is on one of my external drives via USB, it never sends, ever. I have been using this procedure for several months now and it is the only way I can attach an image to a text message.


I agree that it is probably a settings issue. I have brought it up to Apple twice and they have no idea what I'm talking about.


Yes, it bugs the crap out of me, but not enough to sell my MBP and buy a Windows platform.


Apr 21, 2020 5:23 AM in response to Comcat70

I had the same problem.


The problem was an active blacklist on my router. Here I had blocked a few Google addresses.


After I had cleaned up the list a bit, a synchronization for iCloud and iMessage (sending again images) was possible.


Is it very likely that something is going through google due to the increased data volume on the Internet?

Jun 25, 2020 3:17 PM in response to Comcat70

https://macreports.com/cannot-send-or-receve-messages-on-your-mac-fix/comment-page-3/?unapproved=109815&moderation-hash=8844eb3d3f11a9b188ada09b6980845e#comment-109815


6- Your problem may be because of your date and time settings. Lets resolve this. Click Apple menu > System Preferences > and then Date & Time; select the Time Zone tab and the “Set date and time automatically” checkbox, if it is already selected, unselect and wait a few seconds and reselect again. You may need to enter the admin password if the checkbox is dimmed.

Jan 28, 2021 8:28 AM in response to mcasabar

This was exactly my problem. As long as the pictures / files are on the "system"-hard drive everything is fine. The behaviour just starts when I took a picture from a another disk (for example network drive, SD-card, second internal drive, external usb drive).


Thats very anoying when you have to play arround with large amount of files and had to copy it first to the first hard drive.


Does anyone know why iMessage don't send from other drives?

Has it something to do with file system?

Has it something to do with right management?


Wasn't able to do further tests.

But can tell, that my second internal drive is APFS (Encrypted) formated, like my system hard drive - so I would largely rule that out.

Apr 2, 2021 1:21 PM in response to Comcat70

iMessage Photo problem:


I too have had the inability to send a photo as small as 67 KB through messaging with my 2014 MACBook Pro running Big Sur 11.2.3. The message board helped immensely!


As suggested I tried shutting down messaging and restarting it - no luck! Then as suggested by another I transferred the pic from my external drive (WD My passport for MAC) to my internal hard drive documents folder. YES, it worked I was able to send an important pic to my contractor!!!


I have all Apple products, phone, iPads, and two computers, Apple really should have fixed this problem as soon as they became aware of it or at least sent out a temporary fix to all original owners!

Jul 3, 2020 7:14 AM in response to pungme

Quote: “Here’s how i fixed it.


  1. Sign out from iMessage
  2. Finder, Go > Library (Hold option)
  3. Locate Messages folder
  4. delete everything ends with .db
  5. restart the computer
  6. open iMessage and sign in again


Hopefully they fix this issue soon :-/“



so this approach causes you to lose all message archives?? Is there any way to restore files or conversations?

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Macbook not sending pictures in IMessage anymore

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