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I used to send emails to unsecured SMTP servers using nc.exe utility (Windows port of NetCat) and now I need to send the same emails to a secured SMTP server (TLS). What additional parameters do I need to specify in nc.exe or body of the email message to enable secure communication?

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With netcat, it's more-or-less impossible*.

You need a utilty which supports tls/ssl - you can try with snetcat or any other netcat clones.

*you have to do a ssl handshake first, exchange keys, encrypt, send, and then decrypt recieved data

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up vote 1 down vote accepted

The following article explains how to achieve this with the combination of stunnel/blat

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