How to Resend a Message “Not Delivered” from Mac Messages

May 16, 2017 - 12 Comments

Mac Messages icon

The Mac Messages app may occasionally fail to send a message correctly, when a message fails to send it is made obvious by a little red (!) exclamation point and a “Not Delivered” message under the failed iMessage or text message. But you don’t have to retype the message or just let it go, instead you can use a little trick to resend the message again on the Mac.

This works to resend any failed message from the Messages app in Mac OS, including iMessages and text message assuming SMS has been configured to be sent and received from the Mac. Here’s how you can use this neat little trick:

How to Resend a Message in Mac Messages

  1. Confirm the Mac has internet access and online connectivity
  2. From the Messages app on Mac, open the message thread with the failed message that you want to resend
  3. Click on the red (!) exclamation point indicating the message has failed to send and was not delivered
  4. How to resend a message on Mac

  5. A pop-up message will state “Your message could not be sent” click on “Try Again” to resend the message via Messages for Mac
  6. Resend a message on Mac

  7. Repeat with other messages as needed to resend, if applicable

The iMessage or text message will attempt to resend, and usually as long as the Mac has internet access the message will send successfully the second time around when you choose the “Try Again” option.

A similar trick can be done on the iPhone and iPad when messages fail to send from iOS too, again this is usually the result of inadequate internet data connectivity.

Why does a message fail to send?

There can be numerous reasons a message does not go through, but the most common reason is a blip in internet connectivity with the computer (or recipient) going offline. Also, it’ possible that iMessage itself may be down which can be checked easily, though that is rare. Sometimes there is an underlying issue with how iMessage is configured on the Mac too, but if the problem appeared spontaneously that is much less likely.

Another issue you may encounter is the erroneously appearing repeated “message not sent” errors that may show up on a Mac that hasn’t been used in a while yet shares an Apple ID with another active Mac or iOS devices with many messaging activities ongoing.

* Note that when an SMS text fails to send however you may see the (!) red exclamation point but not necessarily a “Not Delivered” message as you would with an iMessage, because SMS lacks the read receipts ability.

Have another trick for resending messages from the Mac? Let us know in the comments!


Related articles:

Posted by: Paul Horowitz in Mac OS, Tips & Tricks, Troubleshooting


» Comments RSS Feed

  1. Colin Greenland says:

    Thanks very much for posting this tip. Solved the problem for me immediately. I haven’t got an iPhone and find Messages so useful for people who depend on them, but it’s such a primitive, unhelpful piece of software. I first bought an Apple Mac because everything was so user-friendly, accessible and intuitive. Not any more, sadly.

  2. nguyen says:

    Command + Option + P + R. Fix error a Message “Not Delivered” from Mac Messages

  3. no way says:

    The ““Your message could not be sent” will automatically appear in Sierra, making this a no brainer (IOW no need for a hint”) issue. As I recall, this also automatically appears in El Crapitan and Yosemite too.

  4. Jean Paul Beauvaise says:

    Had a problem with this a few months back, all our iPads and iMac would suddenly not send or receive messages, the iPhone still did. We use Messages a lot to keep in touch with family. Have been with the same ISP for many years. Tried everything I could think of and spent a couple of frustrating hours on the phone with Apple which included factory resetting one of the iPads trying to find the solution, but that didn’t solve it either. After about three weeks of no messages I tried changing the DNS to the Google Public DNS and and much to my surprise it was fixed! I don’t know enough to know why it fixed it, just glad it did.

  5. ellen pearson says:

    Just got turned down for “already said that.” First time I’ve ever posted here. WTF?

  6. ellen pearson says:

    There is also the option of Send as Text Message. Most of my failed messages send easily as Text Messages.

    Deal with it.

Leave a Reply


Shop on and help support OSXDaily!

Subscribe to OSXDaily

Subscribe to RSS Subscribe to Twitter Feed Follow on Facebook Subscribe to eMail Updates

Tips & Tricks


iPhone / iPad



Shop on Amazon to help support this site