Comment by anthk

MinC for XP and up: (MinC is not Cygwin, you get cc, ncurses, ksh, git and some goodies).

https://minc.commandlinerevolution.nl/english/home.html

IronTCL for XP and up

https://minc.commandlinerevolution.nl/english/home.html

Updated SSL/TLS certs, again for XP and beyond:

https://legacyupdate.net/

Tiny Pascal-like language targetting DOS, CP/M and Unix:

https://t3x.org/t3x/0/index.html It's no Free Pascal but it can do good stuff with very little:

https://t3x.org/t3x/0/programs.html

JimTCL, a tiny TCL with bundled TLS, JSON, Sqlite3 and, optionally, some SDL2 support:

https://github.com/msteveb/jimtcl https://jim.tcl-lang.org/home/doc/www/www/index.html

You can compile JimTCL with MinC under XP, and maybe T3X0 too. With JimTCL you can build a quick TCL expect clone, some netcat clone too with TLS can be done in minutes too, really good for debugging or to create a simple IRC/Email/Gopher/Gemini client in text mode.