As it turns out, Outlook and Outlook express can't do STARTTLS,
they need to do SSL from the get-go. This usually means that the server must listen on a different port for outlook clients (port 465 perhaps), if you've chosen SSL.
So, could it be that your windows clients are not talking to port 25 at all? but instead are talking to a different port on the bellsouth servers?
I'm just trying to suggest a possibility.
Anand Buddhdev wrote:
On Thu, Jun 24, 2004 at 09:17:41AM -0400, Bowie Bailey wrote:
220 mail.bellsouth.net ESMTP server (InterMail vM.5.01.06.08 201-253-122-130-108-20031117) ready Wed, 23 Jun 2004 18:28:26 -0400
EHLO default
250-imf00aec.mail.bellsouth.net
250-HELP
250-PIPELINING
250-DSN
250-8BITMIME
250 SIZE 26214400
Interesting. I get the same response from all their servers, but I'm currently using authentication when I send mail directly from my Windows box. Is it possible that the server accepts authentication, but doesn't advertise it?
Well, that would indeed be quite silly. How would any clients know to authenticate if AUTH isn't advertised?
Are you _sure_ your windows boxes are authenticating? Try doing a tcpdump of the connection between your windows box and the server to see what exactly is going on. I don't know enough about windows mail clients, but perhaps your mail client is falling back to an unauthenticated connection when it can't use SMTP AUTH.
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