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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