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On Thu, 27 Jun 2013 15:21:05 +0100
Joshua Phillips <> wrote:

> HTH,
> > 
> > i have checked for openssl library problems with
> > 
> > openssl s_client -starttls smtp -connect <servername>:<port>
> > 
> > against various mail servers, and it seems that this 
> > works fine ( receiving 250 OK )
> That s_client command uses STARTTLS (the exchange starts with
> unencrypted SMTP and then uses the STARTTLS command to start a TLS
> session). The code on Github uses SMTPS (connects using TLS straight
> away), which is considered deprecated (IIRC) and usually uses a
> different port. You'll have to modify the code to check for STARTTLS
> availability and send the STARTTLS command and receive the
> acknowledgement before doing the TLS handshake.


yes you are of course correct, i only need to delay wrapping the socket 
until after i have issued STARTTLS.  doing so in fact let me continue
with AUTH. 

i will put some code together over the weekend and make it available
somewhere for future reference.

cheers for the hint,