Cross Compiling OPENSSL from WSL/Linux to Windows
Flags for the different binaries need to be overwritten when generating the Makefile with Configure
https://github.com/openssl/openssl?tab=readme-ov-file
./Configure --static -static --prefix=/opt/Cross-openssl/win64 --openssldir=/opt/Cross-openssl/win64 mingw64 CC=x86_64-w64-mingw32-gcc RC=x86_64-w64-mingw32-windres AR=x86_64-w64-mingw32-ar RANLIB=x86_64-w64-mingw32-ranlib
Ref:
https://github.com/openssl/openssl/issues/9922