Outlook and Authenticated SMTP
Every now and then I am completely taken aback by the sheer idiocy that is Outlook. Perhaps more aptly called Outbreak. This morning we were having issues with authenticated SMTP. I telnet to port 25 and it tells me:
The logs tells us outlook is trying to use NTLM, so we disable it:
This causes outlook to switch to no authentication at all. So we somewhat unwillingly turn on plain text auth:
And what do you know, it starts using LOGIN. From experience I already know outlook cannot do PLAIN either.
So you mean to tell me that outlook only supports NTLM and LOGIN?
250-AUTH GSSAPI NTLM DIGEST-MD5 CRAM-MD5
The logs tells us outlook is trying to use NTLM, so we disable it:
250-AUTH GSSAPI DIGEST-MD5 CRAM-MD5
This causes outlook to switch to no authentication at all. So we somewhat unwillingly turn on plain text auth:
250-AUTH GSSAPI LOGIN PLAIN DIGEST-MD5 CRAM-MD5
And what do you know, it starts using LOGIN. From experience I already know outlook cannot do PLAIN either.
So you mean to tell me that outlook only supports NTLM and LOGIN?
posted by ispburger at 1:17 am
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