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Sending emails from O365 account not working

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I can no longer send emails as of today. Instead of O365 SSO login prompt I am getting the old one for wrong password. I did not change any settings for outgoing server, and I can still receive emails with no issues.

The thing is that I have another computer and that one is 102.15.1 version, same thing, cannot send emails.

I've tried to change to OAuth2 for SMTP but no luck, not getting SSO login at all.

Anyone have an idea what's it all about?

I can no longer send emails as of today. Instead of O365 SSO login prompt I am getting the old one for wrong password. I did not change any settings for outgoing server, and I can still receive emails with no issues. The thing is that I have another computer and that one is 102.15.1 version, same thing, cannot send emails. I've tried to change to OAuth2 for SMTP but no luck, not getting SSO login at all. Anyone have an idea what's it all about?
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Chosen solution

Resolved, I switched SSL/TLS and STARTTLS couple of times, with STARTTLS as the chosen option and it seems to be working.

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Chosen Solution

Resolved, I switched SSL/TLS and STARTTLS couple of times, with STARTTLS as the chosen option and it seems to be working.