Yesterday I found that outlook couldnt connect to the mail server while I was working on installing Postfix with STARTTLS on a Plesk server. I could see the following errors in the error log file:
postfix/smtpd[1929]: warning: SASL authentication failure: realm changed: authentication aborted
postfix/smtpd[1929]: warning: SASL DIGEST-MD5 authentication failed: authentication failure
This is while Thunderbird was working fine. The error appears to be from outlook that couldnt send the account credentials using DIGEST-MD5 encryption. The following workaround could be applied:
Edit /usr/lib64/sasl2/smtpd.conf and update:
mech_list: CRAM-MD5 PLAIN LOGIN
Edit /etc/postfix/main.cf and update:
smtpd_sasl_security_options = noanonymous
and finally run:
service postfix restart
service saslauthd restart
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