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 01:59:37AM +1100, Andrew McGlashan wrote:
> Setup email on Windows XP Pro using Outlook Express as follows.
> 
> 
> General tab:
>  mail account:     testaccount
> 
>  user information:
>   name: whatever
>   email address: valid email address
> 
> Servers tab:
>  standard setup for pop but with "My server requires authenticaiton" checked
>    Outgoing mail server settings, "Use same settings as my incoming mail server"
> 
> Advanced tab:
>   Server port numbers:
>     Outgoing 465 with SSL
>     Incoming 995 with SSL
> 
> Once the above is setup okay and tested, close Outlook Express.

As far as I know, this will use SMTP over SSL.

How does your exim reply when you telnet to localhost 465? Does it
show a clear text SMTP banner?

> Install Incredimail [custom without extras checked], it should automatically take the settings from the Outlook Express setup.
> 
> 
> Now when sending an email using Incredimail, you get this popup:
>   "Failed to connect the outgoing server: 'outgoing server name'
>    Please try again later."
> 
> Clicking on "Details" gives this information:
>   "SocketError: -2146885628 , Port: 465, Protocol: SMTP.Cannot find object or property."
> 
> On the Debian mail server, you see the following in the /var/log/exim4/mainlog file:
>   "TLS error on connection from [ip.ad.dr.ess] (gnutls_handshake): A TLS packet with unexpected length was received."  

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.

If you don't see a cleartext "EHLO something", please retry with
openssl s_server instead of the socat.

Greetings
Marc

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