"Message Send Failure" in macOS Messages App Since Upgrading to Big Sur

Yes, while there are tonnes of highly knowledgable people who use Apple products and can circles around some of the people at Genius bars, they aren't unfortunately the people designated as Community Specialists. Frankly, I have no clue how their chosen. They have a pulse? They have a warm body? They were given a troubleshooting guide by Apple and follow it cluelessly?

The reply to your issue is ridiculous. Create another account? Really! ?

Here's one ACTUAL solution that should solve your problem and the many others who appear to share a similar problem.

When you upgrade your phone or mac, yes, sometimes some settings do get changed which sort of breaks how your were doing things. In this case, I believe that the solution to your problem is that your iPhone has been changed to no longer forward your text messages to your Mac. As a result, when you try to send or expect to receive texts from non iPhone users, you can only do it on your iPhone. Your Mac gives a poor message "Not Delivered" ... It sounds like it tried right ?

1. Go to your iPhone, and open the Settings app.
2. From the main page of the Settings app, scroll down and find "Messages". Click on it.
3. On this screen, scroll down until you see "Text Message Forwarding".
4. To the right, you will see if it is setup to forward messages to any of your other Apple devices (iPad, Mac). There will also be a disclosure arrow ">". Tap on it.
5. The screen you are on will say "Allow these devices to send and receive text messages from this iPhone".
6. Turn on the function for any devices like your Mac for which you want your regular text messages to go and from which you want to be able to send text messages to non-iPhone contacts.

And that's it! Now, it is true that this may not be the solution to your problem, but given that this occurred right after the update and that you can still send messages to iPhone contacts, I'm guessing it's likely the solution.

I hope this solves the problem for you and the many others who experience this. I expect it will keep happening on major updates so perhaps this will help future users. I'm sorry I didn't see your message sooner... I usually don't come here but stumbled upon your question.

Found a solution that worked for me on this discussion -> https://discussions.apple.com/thread/7528581

Close all applications, specifically Messages

Reboot

Spotlight search for Keychain Access

Search in Keychain Access for - com.apple.facetime

Right click on and delete - com.apple.facetime: registrationV1 *** Note: I also deleted registrationV2 ***

Reboot

Launch Messages

I'm having the same issue with my MacBook Pro (13-inch, 2019, Four Thunderbolt 3 ports). I can send messages to some contacts but not others. The weird thing is I can send messages on my iPhone to all contacts, even the ones I'm having trouble with on my Mac.

Justin_Canada wrote:

1. Yes, while there are tonnes of highly knowledgable people who use Apple products and can circles around some of the people at Genius bars, they aren't unfortunately the people designated as Community Specialists. 1 -They were given a troubleshooting guide by Apple and follow it cluelessly?

2 - The reply to your issue is ridiculous. Create another account? Really! ?

1 - for legal reasons they must follow published guidelines for troubleshooting. We, as end users like yourself, can recommend what we've learned or tried ourselves with no legal tie to Apple.

2 - What better way to see if there are 3rd party software that is contributing to the problem. A new, vanilla admin account will tell you that. It's a great troubleshooting tool.

absolutely NOT helpful. I have the same issue with some of my contacts and I have already tried everything from your list. I logged out from imessage on all devices, turned it off and on again. It simply doesn't work. It was OK before I updated to Big Sur.

Any other suggestions?

Hey evan169,

We're glad you thought to ask Apple Support Communities about the trouble you're having messaging certain contacts from your Mac. If you haven't already, complete all steps here, including checking your date and time settings: If you can’t send or receive messages on your Mac

If those steps don't help, let's narrow this down by creating a new user account to see if you're able to send messages there. Just in case, here's how to create that new account: Set up users, guests, and groups on Mac

Let us know how it goes.

Take care.

Have you installed the latest system update? You're at macOS 11.1 and 11.6 is available. Try updating the system first and see if the problem persists.

I have the exact same issue and it's driving me nuts!

Identical issue here.

I have been having this issue since last November or whenever Big Sur came out. Super annoying. Good news though! The new MacOS and iOS versions together fix this issue! Update!!!

Yes.!!

the new update has worked for me also!! perfect!!

I have same/similar issue. Certain contacts work and others don't. Software on phone and MacBook are all up to date as of 5/9/21. Any ideas are appreciated.

I am also having this issue. MacBook Pro running Big Sur. 11.4

Help, I am having the exact same issues. Have you resolved your issues since this posting? Except I have a mac air so not sure if pro and air make a difference.

thanks