Can't send any outgoing e-mail from the Apple Mail app on MacBook Pro (M1)

[Ompopo]

So my father have been having a lot of trouble for the last 2-3 weeks where he is suddenly not able to send any e-mails from the Mail app on his MacBook Pro (M1) running macOS 12.5.0. When he tries to send an e-mail he just get a window saying "Can't send message with the servant Hotmail" (might not be right in English as he gets the message in Norwegian) and ask him to try to send it from another outgoing e-mailserver (see image attached).

He has only two accounts connected, his iCloud from his Apple-ID and his Hotmail which is added through Microsoft Exchange.

Have there been any updates or anything here lately that might have caused this? Since it worked earlier but suddenly stopped.

I have tried to remove his Hotmail e-mail from the Accounts-pane in System Preferences, but even when I add it from scratch (choosing Microsoft Exchange) it still won't work.

I've also tried to Google an answer, but I can't seem to find anything. Or I'm using the wrong words/phrases while searching as English is not my native tongue.

 

[ivanwi11iams]

If he logs into his Hotmail account via a browser, it works fine?
Also, I was under the impression that Microsoft were convincing Hotmail users to switch/update their email to Outlook. Wondering if that is now in affect, and he merely needs to remove the account on the MBP, and re-add it as @outlook.com versus hotmail.com...

 

[Ompopo]

If he logs into his Hotmail account via a browser, it works fine?
Also, I was under the impression that Microsoft were convincing Hotmail users to switch/update their email to Outlook. Wondering if that is now in affect, and he merely needs to remove the account on the MBP, and re-add it as @outlook.com versus hotmail.com...

Yeah, he have no problems at all if he logs in through a web browser or on his iPhone. It’s only on his MacBook Pro he has this problem with not being able to send e-mails.

But he has the same problem if he tries to send an e-mail using his @icloud.com e-mail as well, receiving the samme message (sorry for not writing that more clearly in the opening post, I see now it might be read as him only having trouble sending from his @hotmail.com address).

 

[Apple_Robert]

I am guessing that he may have iCloud Relay turned on. If that is the case, trying to turning if off and then see if the problem goes away.

 

[ivanwi11iams]

Also, to confirm, is the WIFI/LAN working on that MBP, i.e., is the internet REALLY working?

 

[Ompopo]

I am guessing that he may have iCloud Relay turned on. If that is the case, trying to turning if off and then see if the problem goes away.

I’ve tried turning iCloud Relay off now, then I restarted the laptop, but still the problem persists

Also, to confirm, is the WIFI/LAN working on that MBP, i.e., is the internet REALLY working?

WiFi is working with no problems at all. The Mail app is downloading all e-mail receives and he can read and open them, just not reply to any. And all other apps and Safari work with no problems.


So thanks for trying, but still it is not possible to send e-mails through the Mail app from either my father’s Hotmail or iCloud e-mail.

 

[ivanwi11iams]

Are you in the same location he is? If so, and you have a MBP, add the account to your MBP. Does it work then? Failing that, can you take the MBP to your place and test it there? Does it work?

In short, you're testing it via another internet connection. Wonder if there is a port or something blocking it on his network...

 

[Ompopo]

Are you in the same location he is? If so, and you have a MBP, add the account to your MBP. Does it work then? Failing that, can you take the MBP to your place and test it there? Does it work?

In short, you're testing it via another internet connection. Wonder if there is a port or something blocking it on his network...

Oh, good idea. He is coming over on a visit in an hour so I’ll ask him to bring the laptop so we can test it on my WiFi 😊 Thanks for the tip, I’ll update when we have tried 👍