Programming challenges? Software archeology?
If I wanted to communicate from outside WinUAE with a running process inside WinUAE, one way to do this is to configure it (under Settings/Host/IO ports/Serial port) to expose the emulated serial port as a localhost address and port. In this folder are various attempts to read from the serial port, with varying degrees of success.
See the relevant README.md for further detail.
WinUAE has a named pipe \\.\pipe\WinUAE that can be used to communicate with the emulator. In
theory it should be possible to interact with running code using this. Commands can be sent to
control both the emulator and running state and this includes the debugger.
The Python script run.py can be used externally on Windows to send commands to this named pipe
and view the output.