The direction is mail sent from an external email address to
stunnel (running on google cloud) for delivery to a postfix mailbox running
on a local network.

I posted this question on serverfault (
https://serverfault.com/questions/1145279/stunnel-smtp-tls-frontend-server-proxy-for-remote-backend-postfix),
and someone said the problem may be either stunnel strips the ip and/or the
the sender is trying to switch to TLS on postfix, not realizing the TLS
connection has already been made by stunnel.



On Sat, Oct 7, 2023 at 9:22 AM Stewart Anderson <[email protected]>
wrote:

> Client and server will both negotiate SSL.  Your server mode is presenting
> a certificate.
>
> It's not clear from your config /text which direction your traffic is
> going !!
>
> If it's incoming from Google to your postfix server then server mode is
> correct.  Stunnel will negotiate the SSL and then forward to postfix in
> clear.  If the handshake isn't happening, have you put Google's cert in
> your CA certs somewhere?
>
> What confuses it for me is the Google internal IP reference.  If you are
> getting traffic from Google then stunnel would need to be accepting on the
> host where stunnel is, so only a port is required in the accept.  This can
> be on a machine in your DMZ or behind a firewall, e.g. on or close to your
> postfix server.
>
> Hope that helps.
>
>
>
>
> Stewart
> [email protected]
>
> On 6 October 2023 05:51:14 "[email protected]" <
> [email protected]> wrote:
>
> I'm running stunnel in server mode and listening on port 587 and trying to
>> connect to a remote postfix server running on port 25.
>>
>> NB: the two servers are connected via zerortier, which may or may no be
>> relevant to the issue.
>>
>> DEBUG = 7
>>
>> [ssmtp]
>> protocol = smtp
>> accept = google_cloud_internal_ip:587
>> connect = remote_zerotier_postfix_ip:25
>> cert = /etc/stunnel/domain.pem
>>
>> I thought this would set up stunnel to handle the TLS handshake and
>> terminate the TLS connection, while proxing to the backend postfix server
>> without requiring postfix to worry about TLS. But I'm getting LOG3[0]:
>> STARTTLS expected when stunnel tries to connect to postfix. If I put
>> stunnel in client mode, then it doesn't negotiate the incoming TLS
>> (right?).
>>
>> What am I missing?
>> _______________________________________________
>> stunnel-users mailing list -- [email protected]
>> To unsubscribe send an email to [email protected]
>>
>
>

-- 
James Thornton, *http://electricspeed.com <http://electricspeed.com>*
_______________________________________________
stunnel-users mailing list -- [email protected]
To unsubscribe send an email to [email protected]

Reply via email to