As the "HTTP Proxy" (actually just nc -l 1080 at the moment), I receive this from Windows 2000:

GET http://glaceon.social/ HTTP/1.0
Accept: image/gif, image/x-xbitmap, image/jpeg, image/pjpeg, */*
Accept-Language: en-ie
Accept-Encoding: gzip, deflate
User-Agent: Mozilla/4.0 (compatible; MSIE 5.01; Windows NT 5.0)
Host: glaceon.social
Proxy-Connection: Keep-Alive

So, I think that all I'd need to do is:

  1. Parse the first line, determine that we're connecting to glaceon.social
  2. Remove the Proxy-Connection header
  3. Establish an encrypted connection to glaceon.social
  4. Send glaceon.social these headers unchanged (except for removing Proxy-Connection)
  5. Send glaceon.social's response back to the Windows 2000 laptop, unencrypted

HTTPS is just HTTP over a TLS-encrypted connection, right? First you set up a TLS-encrypted connection, and then you send regular HTTP headers?

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