Since you're able to use smtplib my suggestion is invalid (I didn't
read carefully enough last time)

Once I faced this problem, and the ehlo output did not have AUTH
(which means AUTH was not enabled on the mail server), and all I did
was remove mail.settings.login line and it started working. Maybe this
will help.

-- Adi

On Jul 27, 8:13 pm, Adi <aditya.sa...@gmail.com> wrote:
> Have you tried using telnet to verify your server and mail are
> correctly configured?
>
> Try this:
>
> c:\> telnet 192.168.200.43 25
> ehlo
> mail from:the...@h**********a.com
> recpt to: t...@h***********a.com
> data
> This is a test message
>
> The recipient should be something valid. If this sends out email from
> your Windows server then the smtp relay is working. In that case
> please attach ehlo output. If this doesn't send out email, then the
> problem is not with your web2py code, but with your mail setup
> somewhere.
>
> -- Adi
>
> On Jul 27, 7:29 pm, Andrew Buchan <andyha...@gmail.com> wrote:
>
>
>
> > Massimo,
>
> > 192.168.200.43 is a different windows box setup as a domino server, and the
> > smtplib example in original post works fine connecting to that server. The
> > windows box hosting the web2py application will not normally be connected to
> > the internet, so I can't go using google's smtp.
> > If I recall from the event log on domino (which I do not have access to
> > myself), the connection seems to be established but then dropped. Perhaps
> > the header is not in a correct format?
>
> > Andrew.
>
> > On Tue, Jul 27, 2010 at 3:06 PM, mdipierro <mdipie...@cs.depaul.edu> wrote:
> > > Is 192.168.200.43:25 the windows box itself or an external unix box?
> > > In the first case, do you have an email server running on windows?
> > > On unix this works because you have postfix but windows does not come
> > > with one.
> > > You may want to use an external smpt server like google.
>
> > > On Jul 27, 9:00 am, Andrew Buchan <andyha...@gmail.com> wrote:
> > > > Thanks, but I tried that, along with a number of other port settings,
> > > > using smtp as prefix etc... Has anyone els managed to get this working
> > > > from a windows server?
>
> > > > On Jul 22, 12:11 pm, Vasile Ermicioi <elff...@gmail.com> wrote:
>
> > > > > > mail.settings.server= '192.168.200.43:25'
>
> > > > >  add port

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