[Exim] Re: TLS versus SMTPS

On Mon, 08 Dec 2003 21:13:24 -0500, James P. Roberts wrote:

> Howdy Kind Folks,
>
> I've hit a snag trying to support M$ Outlook Express (OE), under Win XP
> Home, using both encryption and authentication. The objective is to
> *require* encryption *prior* to authentication.
>

[snip]

> Now, on an old Win98 box, OE behaves "correctly." (And for once, the OE
> smtp.log was useful). On first EHLO to port 25, Exim advertises TLS but
> not AUTH. OE does STARTTLS; this succeeds, then OE does a 2nd EHLO.
> Now, since the connection is encrypted, Exim advertises AUTH. OE
> obliges, and message is accepted for relay. Great. But could M$ leave
> well enough alone? Oh no...
>
> OE under Win XP can't handle this. (Haven't found the smtp logging
> feature, I suspect there isn't one in XP home edition). If I have it
> connect to port 25 directly, Exim never logs a thing; OE fails to send,
> leaves message in outbox, with an error like: '(0x800CCC64) ...failed to
> send... blah blah'.
>

Before you go any further, do you have Norton Antivirus on the XP machine?
If so, and it is set to scan outgoing mail, it intercepts the SMTP port
and feeds it to it's own SMTP server. Problem is, it can't do SSL, so it
barfs at the STARTTLS command. Turn it off.

Dave Hill

--
Dave Hill
Systems Administrator, Newnham Research Ltd
Tel: +44 1223 690771