OpenSSL interoperates with whatever SSL IIS has.  You need to read about 
  configuring IIS and its SSL stuff; Microsoft docs, not OpenSSL docs. 
You might find it easiest to pay someone (like Verisign) to sign the 
cert that you will have IIS generate.  It will take you less time to do 
that, than to figure out the openssl commands.

You do not need a key or cert on the client; you can embed the server 
cert on the client, so that clients can verify the server before sending 
info.

You can use openssl to write your custom client on mac, windows, etc. 
They will need to open a socket to the "HTTPS" port, typically 443, and 
send and receive some HTTP; typically that's pretty easy.

Hope this hhelps.
        /r$

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