I'm using stunnel as a reverse proxy.  I have an smtp server smtp1 and an stunnel server proxy1.  Clients connect to and negotiate ssl on proxy1 which then connects to smtp1 via a plaintext connection.  stunnel does not reside on the client.  If I connect the client directly to smtp1 via ssl it works fine.

On Tue, Jun 5, 2012 at 12:20 PM, Pierre DELAAGE <delaage.pierre@free.fr> wrote:
Hmmm if you are using stunnel on client side (as suggested by your correction) it is that YOU DO NOT WANT TO USE SSL OPTION in OUTLOOK.

because stunnel will act as an "almost transparent' ssl tunnel.

So in outlook : uncheck ssl option and give "localhost" as your smtp server.

and adapt local port according to your stunnel conf.

Apart from that : I use stunnel on the server ONLY, with self signed certificate coming from openssl,
and outlook configured as ssl client is working.
SSLversion = all is always GOOD

works with stunnel 4.20 on linux mandriva 2008, outlook 2007

Pierre



Le 05/06/2012 20:08, James Devine a écrit :

On Tue, Jun 5, 2012 at 10:52 AM, James Devine <fxmulder@gmail.com> wrote:
I am trying to setup stunnel to ssl proxy mail to an smtp server and this seems to work fine for thunderbird but when I try using outlook 2010 to connect via ssl I get the error:

Send test e-mail message: Your server does not support the connection encryption type you have specified.  Try changing the encryption method.

For sslVersion I have the option of SSLv3 and TLSv1, all and SSLv2 do not seem to work so I'm not sure if that is the problem

Anyone else run in to this or know what I might do to resolve it?

I can get it to work if I setup ssl on the end server directly and bypass stunnel


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