On Thu, Nov 23, 2023 at 07:48:33PM +1100, duluxoz via Postfix-users wrote:
> Hi All,
> 
> This may be a stupid Q, but we're getting a `postfix/tlsproxy[89206]: TLS
> handshake failed for service=smtp peer=[104.199.96.85]:25` error in our logs
> when trying to relay via an SMTP Relay Service (both Mailjet and
> Brevo/SendInBlue). Could our issue be related to this LE issue?

No, failure to complete the TLS handshake is not related to any issues
with the certificates.  That said, the handshake works for me:

    posttls-finger: Untrusted TLS connection established to
        104.199.96.85[104.199.96.85]:25: TLSv1.3 with cipher
        TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange X25519
        server-signature RSA-PSS (2048 bits) server-digest SHA256
    posttls-finger: > EHLO straasha.imrryr.org
    posttls-finger: < 250-smtpin.mailjet.com
    posttls-finger: < 250-PIPELINING
    posttls-finger: < 250-SIZE 15728640
    posttls-finger: < 250-VRFY
    posttls-finger: < 250-ETRN
    posttls-finger: < 250-AUTH PLAIN LOGIN DIGEST-MD5 CRAM-MD5
    posttls-finger: < 250-AUTH=PLAIN LOGIN DIGEST-MD5 CRAM-MD5
    posttls-finger: < 250-ENHANCEDSTATUSCODES
    posttls-finger: < 250-8BITMIME
    posttls-finger: < 250-SMTPUTF8
    posttls-finger: < 250 CHUNKING
    posttls-finger: > QUIT
    posttls-finger: < 221 2.0.0 Bye

Unclear why your tlsproxy is having issues.  Perhaps the same problem as
Patrick was having with SELinux?  Don't configure any client
certificates on your end, or don't enable SELinux?

-- 
    Viktor.
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