On Mon, Nov 25, 2024 at 11:52:07AM +0100, Matus UHLAR - fantomas via 
Postfix-users wrote:

> This is Debian 12, postfix 3.7.11 and SSL 3.0.15.

Does Debian do anything similar to RedHat's crypto policy?

> > Note that these ciphers don't enable "forward-secrecy", they use RSA key
> > exchange:
> > 
> >    $ openssl ciphers -V -stdname -s -tls1_2 -v 'HIGH+AES+kRSA+CBC:@STRENGTH'
> >          0x00,0x3D - TLS_RSA_WITH_AES_256_CBC_SHA256               - 
> > AES256-SHA256                  TLSv1.2 Kx=RSA      Au=RSA   Enc=AES(256)    
> >            Mac=SHA256
> >          0x00,0x35 - TLS_RSA_WITH_AES_256_CBC_SHA                  - 
> > AES256-SHA                     SSLv3   Kx=RSA      Au=RSA   Enc=AES(256)    
> >            Mac=SHA1
> >          0x00,0x3C - TLS_RSA_WITH_AES_128_CBC_SHA256               - 
> > AES128-SHA256                  TLSv1.2 Kx=RSA      Au=RSA   Enc=AES(128)    
> >            Mac=SHA256
> >          0x00,0x2F - TLS_RSA_WITH_AES_128_CBC_SHA                  - 
> > AES128-SHA                     SSLv3   Kx=RSA      Au=RSA   Enc=AES(128)    
> >            Mac=SHA1
> > 
> > So, my money is on RSA key exchange being disabled in your OpenSSL,
> > unless there are other Postfix settings you've not shared that do that.
> 
> I can see these ciphers when I fed the command above with contents of
> tls_medium_cipherlist/tls_high_cipherlist

Have you tries connecting to this server with:

    $ openssl s_client -connect <hostname>:25 \
        -starttls smtp -tls1_2 -cipher 'HIGH+AES+kRSA+CBC:@STRENGTH'

Seems like determining whether the ciphers could interoperate is the
first step.

> Looking back at pcap output:
> 
> Alert Message
>     Level: Fatal (2)
>     Description: Handshake Failure (40)

That's not useful, without known which party sent the alert.

> Now I am not even sure it's problem of ciphers (don't that error produce
> different output?), can this be caused by other property?
> 
> Signature Hash Algorithms (10 algorithms)
>     Signature Algorithm: rsa_pkcs1_sha256 (0x0401)
>     Signature Algorithm: ecdsa_secp256r1_sha256 (0x0403)
>     Signature Algorithm: rsa_pkcs1_sha384 (0x0501)
>     Signature Algorithm: ecdsa_secp384r1_sha384 (0x0503)
>     Signature Algorithm: rsa_pkcs1_sha512 (0x0601)
>     Signature Algorithm: ecdsa_secp521r1_sha512 (0x0603)
>     Signature Algorithm: rsa_pkcs1_sha1 (0x0201)
>     Signature Algorithm: SHA1 DSA (0x0202)
>     Signature Algorithm: ecdsa_sha1 (0x0203)
>     Signature Algorithm: MD5 RSA (0x0101)

Let's avoid random guesses.

-- 
    Viktor.
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