"Message Send Failure" in macOS Messages App

Hi nathan_h,

Welcome to Apple Support Communities. We understand that you're having an issue with sending iMessages to other iPhone users from your Mac. We'd like to help.

Just to confirm, you're experiencing this issue on your MacBook Pro but do not have this same issue with your iPhone or other Mac. Is that correct?

If so, let's focus on your MacBook Pro. Have you closed Messages on your Mac and restarted it? If not, those steps can help in situations like this. Follow these steps to get that done:

Force an app to quit

1. Take either of these actions:

* Press these three keys together: Option (or Alt), Command, Esc (Escape).*

* Or choose Force Quit from the Apple menu  in the corner of your screen.

2. A Force Quit window opens. Select the app that you want to quit, then click Force Quit.

You can even force the Finder to quit, if it stops responding: Select Finder in the Force Quit window, then click Relaunch.

Then, go ahead and restart:

Manually restart

1. Press and hold the power button on your Mac until it shuts off.

2. After a moment, press the power button again to start your Mac. You may lose unsaved changes in open documents.

Hope that helps. Let us know.

Take care!

Hello nathan_h,

Thanks. You might want to try turning off Text Message Forwarding, restarting all devices involved, and turning it back on.

Forward SMS/MMS text messages from your iPhone to your Mac or iPad

If that also doesn't help, and since your settings seem fine and the other troubleshooting didn't help, please contact Apple Support to have them dig more into this with you.

Contact Apple Support

Thanks.