Hi! Microsoft switch personal Outlook.com accounts to OAuth 2.0 for SMTP. If Thunderbird is still pointing at the old smtp-mail.outlook.com endpoint, it never offers the OAuth2 choice and every send attempt falls back to a method Microsoft now rejects, so you see the “SMTP authentication error.” Switch the SMTP host to smtp.office365.com, re-selecting STARTTLS + OAuth2, and let Thunderbird open the Microsoft sign-in window should fix the issue on all supported versions of Thunderbird .
I cannot send emails via SMTP on third-party software
Hi.
When I log in to my account via a third-party software, in this case Thunderbird, I cannot send emails via SMTP.
I can receive emails, so I know the IMAP is well configured. Sending emails also works on the web. It's just a SMTP problem.
For SMTP, I tried both:
- smtp-mail.outlook.com, port 587, STARTTLS, Oauth2
- smtp.office365.com, port 587, STARTTLS, Oauth2
- which is a configuration I found in the forums.
I have a personal subscription, so I don't know which would apply. In any case, none of them work. I always get a SMTP authentication error.
I tried removing and adding the account again, to no avail. This happens in 2 different PCs.
Note: this email account is a legacy account ending in @netcabo.pt, which used to be email accounts provided by a Portuguese ISP, back in the day. Nowadays, they are Microsoft/Outlook email accounts, keeping the domain.
Outlook | Web | Outlook.com | Settings
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Jeronimo Fuerte 16,785 Reputation points Independent Advisor
2025-08-08T00:54:55.8933333+00:00