Help with Authenticated SMTP

[JonThompson]

I attempted to turn Authenticated SMTP (MD5) on for a client. It worked for the first day, then we started to get occasional problems where emails would not be authenticated. The client would quit Mail and open it, and it would sometimes resolve itself. This is occurring on several computers using Mail and/or Entourage v.X.

I would really like to turn on Authentication, rather than the IP-based system that is active now, but it needs to be stable.

[JonThompson]

I am running 10.3.4. I am looking in the logs without seeing anything strange. In fact, I don’t see any entry for denied access, except when a username is wrong due to a mistype.

Could it be an issue with how the keychain stores MD5, which causes the client to error before even attempting to connect?

[Author]

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