Drew Calcott wrote: > Has anyone come across this before? I had a search through the archives / FAQ > and was unable to see anything directly related.
It has some really weird behaviour and expects strange things at the server greeting. I never got around to figuring out exactly what it was doing, but I did find a way for it to talk to an exim box without having a cow but still doing what I wanted. Connecting on a TLS on connect port doesn't seem to work. Best guess - Outlook expects that the connection will be plaintext and then once it sends a command it will head into TLS mode (as far as I can tell). TLS on connect doesn't work like this so ... eh. Pretty sure outlook is in the wrong. Only allowing authentication to encrypted connections doesn't work either as Outlook will NEVER attempt to authenticate if it didn't see a listing of valid AUTH types in the initial server greeting it got before heading into STARTTLS. It doesn't matter that they are present in the second EHLO - I didn't actually check if Outlook sends a second one anyway. In outlook - setting "This server requires TLS" makes it fail. Never looked into it but it might be something similar to TLS on connect stuff. In the end I had the following settings in outlook and exim: exim: Advertise AUTH to everyone on the submission port (587), encrypted or not and used ACLs to prevent unencrypted use of AUTH even though this still allows people to send their credentials in plain text if something is misconfigured. Advertise tls on 587, kill the TLS on connect port. Outlook: turn off anything that requires encryption, and set everything to use TLS if available. plonk in the username and password into the "my server needs authentication with these details" type box. Overall, a bit of a fight. Even after all that, Outlook will occasionally ignore the TLS entirely and just try to authenticate without TLS. Closing down Outlook and restarting it seems to magically fix this and it wont happen again for a week or two. Good luck :) I just swap people over to Thunderbird if they have too many problems. -- ## List details at http://lists.exim.org/mailman/listinfo/exim-users ## Exim details at http://www.exim.org/ ## Please use the Wiki with this list - http://wiki.exim.org/
