Jerry: > $ ldd /usr/local/libexec/postfix/smtp > /usr/local/libexec/postfix/smtp: ... > libssl.so.8 => /usr/local/lib/libssl.so.8 (0x800b2f000) > libcrypto.so.8 => /usr/local/lib/libcrypto.so.8 (0x800c93000)
That looks like the right OpenSSL version. Can you connect from the same FreeBSD box to the same hotmail server with "openssl s_client"? $ openssl s_client -starttls smtp -connect 65.55.96.11:25 Somewhere in the output will be a protocol version, something like: SSL-Session: Protocol : TLSv1 Cipher : RC4-MD5 If "openssl s_client" fails, try adding the protocol: $ openssl s_client -tls1 ... Meanwhile I'll set up openssl-1.01a on a box that has access to remote port 25. Wietse