I have a PHP web application this is failing to relay emails via SMTP/TLS through an opensmtpd-5.4.2_4,1 server. Same webapp relays emails to same opensmtpd server no problem when using SMTP with no encryption.

OpenSMTPD server log entries:

5:46:11 email smtpd: smtp-in: New session d524ae92d73bc34c from host 192.168.0.10 [192.168.0.10] 15:46:11 email smtpd: smtp-in: Bad input on session d524ae92d73bc34c: 500 5.5.1 Invalid command: Pipelining not supported
15:46:11 email smtpd: smtp-in: Closing session d524ae92d73bc34c

On PHP webapp server

root # ldd /usr/local/lib/php/20131226/openssl.so
/usr/local/lib/php/20131226/openssl.so:
        libssl.so.6 => /usr/lib/libssl.so.6 (0x801222000)
        libcrypto.so.6 => /lib/libcrypto.so.6 (0x801478000)
        libc.so.7 => /lib/libc.so.7 (0x80081b000)

Maybe the webapp, which depends on php56-openssl is using the (old!) stock version of OpenSSL on FreeBSD 9x OpenSSL 0.9.8y, and that's why it's failing?
--
Seth
I <3 nicely trimmed email replies

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