From: Grzegorz Adamiak <gadamiak@docucollab.com>
  To  : <masqmail@marmaro.de>
  Date: Tue, 26 May 2009 22:16:26 +0200

Re: [masqmail] Error: unexpected response from TLS/SSL wrapper

--- markus schnalke [2009-05-26 21:13]:
> What about the first ``250 PIPELINING'' line? Does it get removed my
> the stderr redirect? Is it a copy'n'paste fault?

It's simply not there.

> Normally, there should be a 220 greeting line. Maybe that gets read by
> openssl before doing STARTTLS :-?
> 
> In your first message, you wrote:
> 
>> * /usr/bin/openssl s_client -connect smtp.gmail.com:587 -starttls
>>   smtp -quiet -CApath /etc/ssl/certs/ 2>/dev/null
>>
>>   This results in timeout error as nothing is returned by OpenSSL.
> 
> Seems as if Masqmail should try to say ``EHLO'' and see if a reply
> comes then. (Because the greeting message was already read by openssl
> and does not come to Masqmail.)
> 
> Unfortunately, I don't have deep knowledge in this field. It's all
> just guessing :-/

Neither do I. Anyway, I'm lucky Google accepts connections on 465 too.

>> BTW, why the "Return-Path" header in messages from list points to your 
>> address instead of the list's one?
> 
> Don't know ;-) I changed something now ... we'll see.

Sorry, my mistake. Your Return-Path was OK. It should point to your 
address, as it's used to return mail if it fails to be delivered.

I thought about "Reply-to", which is absent and should point to maillist 
address (<masqmail@marmaro.de>). See RFC5322, 3.6.3. "Destination 
Address Fields", <http://www.rfc-editor.org/rfc/rfc5322.txt>;.

-- Grzegorz