On Mon, Aug 02, 2021 at 02:29:14PM +0000, Eric Shields | Mass Transit Honchkrow 
wrote:

> So when I send an email, it doesn't get past the SYN_SENT stage of the
> TCP handshake. In addition, it does not leave my NAT device.
> 
> I currently have my domain's DNS record pointing to the endpoint, but on
> the computer itself, it is pointing to the private IP of the address. It
> sends the private IP out rather than the WAN IP despite adding source
> NAT rules.

Debugging your firewall NAT configuration is not a Postfix topic, and is
best discussed on a firewall-specific list.

You don't need to use Postfix to test outbound connections, just use
"telnet", "nc", ...

> The output of postconf -n:
> inet_interfaces = $myhostname

Why not "all"?

> relayhost = [165.22.191.194]:587

Is this correct?

    $ posttls-finger "[165.22.191.194]:587"
    posttls-finger: Connected to 165.22.191.194[165.22.191.194]:587
    posttls-finger: timeout while reading server greeting

> smtp_bind_address = [wg0_private_ip]

Is this correct and necessary?  Typically the right IP address is
chosen automatically...

-- 
    Viktor.

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