Bug#459323: exim4: Incredimail problem sending email using Exim4 SMTP over SSL / TLS error on connection from [ip.ad.dr.ess] (gnutls_handshake): A TLS packet with unexpected length was received.

[Marc Haber]

On Sun, Jan 06, 2008 at 10:51:21PM +1100, Andrew McGlashan wrote:
> Marc Haber wrote:
> > How does your exim reply when you telnet to localhost 465? Does it
> > show a clear text SMTP banner?
> 
> www:/tmp# telnet localhost 465
> Trying 127.0.0.1...
> Connected to localhost.
> Escape character is '^]'.
> Connection closed by foreign host.
> 
> 
> [had to press ctrl-c to get the last line]

Ok, that looks like your exim is indeed doing smtp-over-SSL on tcp/465.

> > Please let's find out whether Incredimail does really really use SMTP
> > over SSL. On your exim server, run
> >
> > $ echo "220 " | socat TCP4-LISTEN:4465 -
> >
> > and configure incredimail to use "Outgoing 4465 with SSL". Then try
> > sending a message.
> >
> > When you see a cleartext "EHLO something" on the socat shell,
> > Incredimail is trying to do ESMTP STARTTLS, which will need a
> > differently configured exim than Outlook Express does.
> 
> 
> www:/tmp# echo "220 " | socat TCP4-LISTEN:4465 -
> L3
> À       @dbcÎêÕ¢ÅETݳܺÔPuTTYwww:/tmp# PuTTY

I am rather confused by the PuTTY string here. But it surely doesn't
look like cleartext SMTP.

Greetings
Marc

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