Hello Noel,
As you suggest, I enabled TLS wrappermode on both senders servers and the
internal server, set  "smtp_tls_security_level =  encrypt " to senders
servers and it seems perfect now.
Thanks a lot Noel and Thank you all too!
Samuel

Le mer. 17 août 2022 à 17:42, Noel Jones <njo...@megan.vbhcs.org> a écrit :

> On 8/17/2022 10:04 AM, Sam R wrote:
> >
> > Currently I use the following settings:
> > transport_maps = hash:/etc/postfix/transport
> > domain.fr <http://domain.fr> smtp:[192.168.X.X]:465
> > This works but I get the following Postfix message:
> > SMTPS wrappermode (TCP port 465) requires setting
> > "smtp_tls_wrappermode = yes", and "smtp_tls_security_level =
> > encrypt" (or stronger)
>
> Apparently you're sending plain text mail to port 465. Standard
> practice is for port 465 to use smtps TLS wrappermode.
>
> >
> > If I put these additional settings, it doesn't work anymore because
> > the internal address of my servers doesn't match the certificate
> > that is created with the external addresses (I have a handshake failure)
>
> This likely has nothing to do with certificate verification.
>
> Apparently the internal server isn't configured for TLS
> "wrappermode" on port 465 causing the delivery to fail when you turn
> on encryption.
>
>
> You have a couple of choices...
>
> - Configure the internal server to use TLS wrappermode on port 465,
> and enable wrappermode as the log warning suggests.
>
> - Use a different port, possibly 587. Likely the two systems will
> negotiate STARTTLS and send mail encrypted.
>
>
> If you need further help, share your "postconf -nf" and "postconf
> -Mf" and the actual log lines of both successful delivery and what
> happens after you add the -o smtp_tls_wrappermode=yes
> http://www.postfix.org/DEBUG_README.html#mail
>
>
>
>    -- Noel Jones
>

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