This probably exists already, but I am considering making software that lets you connect a classic OS such as Windows 95 or very early Linux with modern HTTPS or SSH by acting as a translation layer to convert the connection to HTTP or insecure Telnet.
I'm probably going to write this using Java 1.0.2, which allows for you to use it on the mass majority of 32-bit operating systems. Is there any reason not to do this beyond "the usecases are very limited?"