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

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