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

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



5. 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!