Le 08/04/2020 à 12:42, Gerard E. Seibert a écrit :
> postfix 3.6-20200316
> FreeBSD 11.3 p7
> OpenSSL 1.1.1f 
> 
> For several years, I was able to sent mail via Outlook. Suddenly, as of
> yesterday, it fails.
> 
> This is the log output from one attempt from postfix:
> 
> Apr  8 05:33:46 scorpio postfix/smtp[73032]: Trusted TLS connection 
> established to smtp.office365.com[40.97.124.210]:587: TLSv1.2 with cipher 
> ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits)
> 
> Apr  8 05:33:46 scorpio postfix/smtp[73032]: 48xzc94xjxz5cMW: SASL 
> authentication failed; cannot authenticate to server 
> smtp.office365.com[40.97.124.210]: invalid parameter supplied
> 
> I know this is not a postfix problem; however, I was wondering is
> anyone had any ideas as to what might have suddenly happened.
> 

I got this problem sometime ago. It was due to a difference in the NTLM
used by postfix (I think it comes from dovecot) and the one used by MS.
Adding
smtp_sasl_mechanism_filter = plain, login
made things work again

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