I've tried logging out and back into my Apple ID account on my Mac, but some (not all) messages are showing the red exclamation point and "Not Delivered", but when I go to the same thread on my phone the message shows up as delivered. I've also checked some of them with one of the people I was chatting with and they are being delivered.

This behavior started 2 or 3 weeks ago.

one message with "! Not Delivered" and another with "Delivered"

  • 1
    I do not have the same problem, but Messages.app on HighSierra is at least a little buggy. Sometimes I will send a text message through my Mac and it will go to the bottom, but when the other person replies it will go above my sent message. It will happen many times in a row, causing all my text messages to appear below the other person's. That's with text messages anyways. – cmarangu Feb 21 '18 at 17:48
  • after about a month (total) this stopped happening. I didn't do anything to solve it. – dwightk Mar 20 '18 at 16:47
  • lol. did you update your macOS? – cmarangu Mar 20 '18 at 18:56
  • nope... nothing changed except the Not Delivered messages went away (well, they stopped appearing for new messages... the old ones are still there) – dwightk Mar 20 '18 at 19:01
  • As for me the text messages are still in their glitched out order. I haven't texted from Messages.app recently, though. – cmarangu Mar 20 '18 at 19:08

What are the chances? I just helped someone with this an hour ago. This worked for her.

It appears that the messages database is corrupted. The only fix is to remove all messages.

From here with edits

  • Quit out of Messages for Mac

  • Go to Finder

  • Hit Command+Shift+G to bring up the “Go To Folder” window

  • Enter ~/Library/

  • Move the Messages folder to Trash

  • Restart the Computer

  • Open Messages (Nothing should be there) and Test

If it works, great! Otherwise comment back here.

Note: This will delete all messages from your Mac

| improve this answer | |
  • @TylerNZ If this helped you please upvote it by pressing the upward arrow to the left of the answer. – JBis Aug 1 '18 at 19:49
  • This is working so far on 10.13.6 – Tom Aug 20 '18 at 13:54
  • I read "Restart" as restart the messages application. It definitely means restart the computer! – Bill Shirley Sep 24 '18 at 15:50
  • 1
    @BillShirley Fixed. – JBis Sep 24 '18 at 16:13
  • This happens constantly to me ... never knew how to fix it! Thanks :) – drfence Dec 12 '18 at 15:51

This solution worked for me by Ralph Johns from Messages says "Not delivered" on Apple Support Communities. It seems to be the same problem as described here.

AS a test deselect the iPhone Number as a Receive Item (it will close the Drop Down for Start Conversation From) so that the Mac can only Send (And Receive) from the Apple ID

Now start a New Message.
in the "to" spot type in your iPhone Number in full including the country code.
(The My Details are not called up if you try your name as you are not expected to call yourself).

Before send go to the iPhone > Settings > Messages > Send and Receive and deselect the Apple ID (don't log it out just deselect it).
This bit will stop any Sync copy showing up from the Send of the Apple ID on the Mac.

Now send an iMessages from the Mac.

Does the iPhone Receive it ?
If not then the Apple ID is not logging in properly on the Mac.
As a first Step try Logging out (Sign Out button) on the Mac version. Quit the app before relaunching the app and signing back in again.

Repeat the test above. If it still does not work then use this Users Tip When the iMessages account will not Login
There is no way to speed up the last section where you have to contact Apple Support and get yourself moved up the chain of Responders until one can look at the Server and tell if your Apple ID when used from the Mac for iMessages is blocked. (your serial number is used for a device specific login so only one device can be block meaning the ID works in other places and devices).
You then still have to wait for the Engineers to reset your ID.

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  • Another USELESS downvote without a helpful explanation on an answer that apparently actually worked. – WGroleau Aug 29 '18 at 13:22

In my case I needed to Settings->Messages->Text Message Forwarding on the iPhone and deselect old devices there, plus select and confirm new one (the one I had trouble with).

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  • This worked for me. I set up a new mac desktop and couldn't send iMessage to non-iPhone users. It was saying Not Delivered. Then I went to my iPhone and selected the new desktop under "Text Message Forwarding". Then I was able to send SMS to non-iPhone users from Desktop – pcantalupo Feb 13 at 14:31

After loooooong time, I rebooted my mac and now looks like the "Not Delivered" messages issue is gone.

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  • Same happened to me recently. Just magically fixed itself after some period of time. – drfence Mar 20 '19 at 17:58
  • And this continues ... it comes and goes. – drfence May 24 '19 at 19:59

Deleting the Messages folder in ~/Library is a bit heavy handed. Since I don't have this issue in all of my conversations, I decided to simply try deleting the problematic Conversation. It appears to be working fine now.

Update: The dreaded "Not Delivered" has returned. Trying deleting the Messages folder this time.

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