This is a two part process.  First check to see if the server supports TLS by doing the following:

• telnet mail.server.com 25
  220 mail.server.com ESMTP PostFix
• ehlo testing
  250 mail.server.com
  250-PIPELINING
  250-SIZE 10240000
  250-VRFY
  250-ETRN
  250-STARTTLS
• quit

Once you have determined that starttls is a supported command do this:

openssl s_client -starttls smtp -crlf -connect mail.server.com:25

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I am currently working at a large retailer charged with creating a test process for all print drivers that will be used in there print environment.  Rather than reinvent the wheel I checked out some great articles Microsoft had using AppVerifier.  After setting up AppVerifier your expected to run tests, aka create your print queues, print content, and check out what happens.  Unfort I didn't want to produce reams of content if I could aviod it. 

The idea was to create what appeared to the windows server as a jetdirect that actually just tossed out the assembled bits.  I used my linux box to create a print queue that wrote to /dev/null and modified xinetd to pass the jobs from port 9100 to the print queue.  Walla, a virtual jetdirect without the mess.

• Created a queue writing to /dev/null 
• Create a file /etc/xinetd.d/jetdirect
  service jetdirect
  {
  socket_type = stream
  protocol = tcp
  wait = no
  user = lp
  server = /usr/bin/lp
  server_args = -d -o raw
  groups = yes
  disable = no
  }
• Service xinetd restart
• Test it out

Now windows thinks its printing to a valid jetdirect and I can do all my testing without wasting paper!

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