On Wed, May 14, 2025 at 01:36:09AM +1000, Matthew J Black via Postfix-users 
wrote:

> But what do you get with 'openssl s_client -starttls smtp -connect
> mail.peregrineit.net:587' - cause I get :

The difference is that OpenSSL defaults to sending an SNI extension with
the server hostname, while Postfix does not.  With posttls-finger it is
possible to specify an SNI name to include in the TLS client hello:

    $ posttls-finger -cC -F /etc/ssl/cert.pem -lsecure 
"[mail.peregrineit.net]:587" |
        openssl x509 -subject -dates -noout
    subject=CN=peregrineit.net
    notBefore=Apr  4 05:28:03 2025 GMT
    notAfter=Jul  3 05:28:02 2025 GMT

    $ posttls-finger -s mail.peregrineit.net -cC -F /etc/ssl/cert.pem -lsecure 
"[mail.peregrineit.net]:587" |
        openssl x509 -subject -dates -noout
    subject=CN=peregrineit.net
    notBefore=Jan 10 07:36:43 2025 GMT
    notAfter=Apr 10 07:36:42 2025 GMT

So, it seems your server has an SNI-dependent certificate configuration,
likely via "tls_server_sni_maps", which store your private key and
associated certificate chain, and need to be updated via "postmap -F".

Had you posted "postconf -nf" output, this would have been apparent.

-- 
    Viktor.
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