Fix Repeated “Your message could not be sent” Messages Error on Mac

Apr 7, 2017 - 18 Comments

Your message could not be sent error on Mac Messages

Mac users may encounter a pop-up error originating from the Messages app in Mac OS which informs them “your message could not be sent”. Often when this error dialog appears, it’s seemingly out of nowhere or when a Mac wakes from sleep or has rebooted.

While it’s possible to encounter the “your message could not be sent” error for legitimate sending failures, or because iCloud or iMessage is down (very rare), it’s also possible the error can appear due to a syncing issue in which case there is nothing to adjust, and the solution in that case is a bit goofy.


The full text of the error you might see, as well as the three options is: “There was an error sending the previous message. Would you like to send it again? Ignore – Open Messages – Resend Message” You can choose ignore, and the error likely comes right back immediately. You can choose Open Messages, and you will also usually see the same error again. If you choose “Resend Message” if there wasn’t a failed message, you may end up re-sending an old message, or nothing may happen at all. Clear as mud, right? Anyway since this is a bit of a nuisance, here is what you should do if you experience this on a Mac.

1: Check iMessage & iCloud Settings

Before anything else, make sure iMessage settings and iCloud are enabled as expected on the Mac. It’s possible to encounter this error message when an iMessage or text message has actually failed to send from the Mac, in which case you can almost always resolve the issue by double-checking Messages app preferences and making sure the Mac is configured to send messages, text messages, and has iCloud enabled and logged in.

  • Check the “iCloud” system preference panel and make sure iCloud and Messages are enabled and logged in as expected.
  • From the Messages app, pull down the “Messages” window and choose Preferences, and make sure account settings are configured and enabled as expected.

2: The Repeatedly Cilck “Ignore” Solution

Yes, it’s just as dumb as it sounds! If you continuously encounter the “Your message could not be sent” error when turning a Mac on after it has been off for a while, or waking a Mac from sleep after it has been asleep for a while, the error could be due to a curious syncing issue with the Messages app, and not an actual message send failure. The solution in this case is to repeatedly ignore the dialog window, which seems to reappear for about the total number of messages which need to sync with another iOS device or Mac using the same Apple ID.

So, what do you do? Click the “Ignore” button. Click it many times. The dialog window keeps reappearing, so keep clicking “Ignore”. Yes I know, this sounds goofy because it is goofy.

Endless iMessage error popups on Mac

Eventually, the error message goes away, presumably because all of the unsynced iMessages will have synced properly between all same-Apple ID Apple devices and things will work again as expected.

Do you have another solution to this error? Perhaps you know another cause? Let us know in the comments.

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Posted by: Paul Horowitz in Mac OS X, Troubleshooting

18 Comments

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  1. junebeetle says:

    You can just hold ESC or Spacebar (if you have the full keyboard control on).

  2. Sandy says:

    Is osxdaily purely concerned with Mac issues now or are you still doing articles relating to iOS?

    • Paul says:

      This is an article about resolving a problem on the Mac which relates to syncing messages with other Macs or iOS devices.

      We have articles about iOS frequently, including the day prior as well as today…

    • Kevin says:

      Sandy, I think you’re missing the point of the website. It’s called OSXdaily. You know what OSX means don’t you or does a tutorial need to be created for just you?☺️😳

  3. Zeek says:

    Pop-up window Force Quit Application

    Select Messages

    Select Force Quit in this and the following pop-up.

    Nuke the damn thing from orbit. Easier on the hands.

  4. Jim Roberts says:

    I keep getting this w/ *email* msgs. I had several attachments. The weird thing is I started to resend and the person stated she had received my message and all the attachments (7) for our organization.

  5. Marcus says:

    I have the same issue! Since I updated my iPhone to 10.3.1 and my Mac to 10.12.4, I cannot send regular text messages from my Mac or my iPad. I still RECEIVE text messages on both the Mac and iPad, and iMessage works great, but I cant send text messages from these two devices (which I could before). Very annoying!

    • JohnW says:

      This is my issue as well. Services worked prior to this last update and now I am having Messages issues (on my mac only) with those who do not have iPhones.

      • MalcolmB says:

        Same here. I don’t have an “ignore” option, just “cancel” and “try again”

        In Messages, it says my iCloud account is enabled, but I don’t see Messages in the roster for iCloud in System Preferences. Should Messages be listed in the iCloud system panel?

  6. Rod Dalitz says:

    It’s a shame, Apple used to “just work” but now I frequently see a mismatch in the number is unread emails. Syncing ought to be easy enough.

  7. Luke L. says:

    I have this messages issue repeatedly on both of my Macs. Thanks for the tips.

  8. LVC says:

    Actually — you have it all wrong!!!! fix is simple. You need to turn on SMS RELAY on iPhone. Go to Settings > Messages > Text Forwarding > allow devices (listed) to send and receive text messages from “this” iPhone.

    Problem solved.

  9. Dan says:

    LVC has the fix. I had this same issue continuously and didn’t realize I had not enabled forwarding on my MacPro – Once I did, the issue stopped for me too. Much better than repeatedly pressing “Ignore” only to have to KEEP doing it every time the machine wakes up. (until the next ‘update’ ??) We’ll see…

  10. Brad says:

    I have Text Forwarding set to on, and I’ve tried turning it off and back on etc. Also factory resetting both iPhone and iMac.

    But the current beta version of the OS lets me receive text/imessages on my desktop/laptop, but not send. Everything still works on iPhone and iPad.

    I’ve submitted a few bug reports. Glad to hear others are experiencing this issue.

  11. Jessica says:

    I started having this issue a few months ago. It only happens when I am sending a photo or video. If I delete the photo or video from the message on the mac (that failed to send) the error message stops coming back… but happens every time I send or receive any kind of media.
    I tried deleting my messages library from the library folder and that didn’t work. I also tried turning off and on the message forwarding as suggesting above. Not sure what else to do!

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