On Monday 04 December 2017 13:19:41 Giovanni Bechis wrote:
> On 11/10/17 17:46, Joel Sing wrote:
> [...]
> 
> > I suspect this is going to be difficult to track down without being able
> > to see what is on the wire (tcpdump or 'smtpd_tls_loglevel = 3' in
> > postfix) or being able to reproduce/trigger TLS sessions from the client.
> 
> postfix log file with 'smtpd_tls_loglevel = 3' attached.
>  Thanks & Cheers
>   Giovanni

Looking at this more closely, it is actually a different problem from the
originally reported issue (wrong version number):

Dec  4 13:09:30 thor postfix/smtpd[91646]: connect from 
sonic301-3.consmr.mail.bf2.yahoo.com[74.6.129.42]
Dec  4 13:09:31 thor postfix/smtpd[91646]: setting up TLS connection from 
sonic301-3.consmr.mail.bf2.yahoo.com[74.6.129.42]
Dec  4 13:09:31 thor postfix/smtpd[91646]: 
sonic301-3.consmr.mail.bf2.yahoo.com[74.6.129.42]: TLS cipher list 
"aNULL:-aNULL:HIGH:MEDIUM:+RC4:@STRENGTH"
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:before/accept 
initialization
...
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 read client hello B
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 write server hello A
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 write certificate A
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 write key exchange A
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 write server done A
...
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 flush data
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:SSLv3 read client 
certificate A
Dec  4 13:09:31 thor postfix/smtpd[91646]: read from 4F66840F900 [4F6048AA003] 
(5 bytes => -1 (0xFFFFFFFFFFFFFFFF))
Dec  4 13:09:31 thor postfix/smtpd[91646]: read from 4F66840F900 [4F6048AA003] 
(5 bytes => 5 (0x5))
Dec  4 13:09:31 thor postfix/smtpd[91646]: 0000 15 03 03 00 02                  
                 .....
Dec  4 13:09:31 thor postfix/smtpd[91646]: read from 4F66840F900 [4F6048AA008] 
(2 bytes => 2 (0x2))
Dec  4 13:09:31 thor postfix/smtpd[91646]: 0000 02 2e                           
                 ..
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL3 alert read:fatal:certificate 
unknown
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept:failed in SSLv3 read 
client key exchange A
Dec  4 13:09:31 thor postfix/smtpd[91646]: SSL_accept error from 
sonic301-3.consmr.mail.bf2.yahoo.com[74.6.129.42]: 0
Dec  4 13:09:31 thor postfix/smtpd[91646]: warning: TLS library problem: 
error:14037416:SSL routines:ACCEPT_SR_KEY_EXCH:sslv3 alert certificate 
unknown:/usr/src/lib/libssl/ssl_pkt.c:1205:SSL alert number 46:
Dec  4 13:09:31 thor postfix/smtpd[91646]: lost connection after STARTTLS from 
sonic301-3.consmr.mail.bf2.yahoo.com[74.6.129.42]
Dec  4 13:09:31 thor postfix/smtpd[91646]: disconnect from 
sonic301-3.consmr.mail.bf2.yahoo.com[74.6.129.42] ehlo=1 starttls=0/1 
commands=1/2

In this case the client hello has been received and the server
hello/certificate/key exchange/done has been sent, before the other side
responds with a "certificate unknown" alert - this suggests that the TLS
client is actually expecting to do some form of certificate verification
and this is failing. 

Was this working prior to OpenBSD 6.2?

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