stunnel Windows install notes Cross-compiling stunnel from source with MinGW (optional): 1) Install the mingw32 cross-compiler on a Unix/Linux machine. On Debian (and derivatives, including Ubuntu): sudo apt-get install gcc-mingw-w64-i686 On Arch Linux: sudo pacman -S mingw-w64-gcc 2) Download the recent OpenSSL and unpack it: tar zvxf ~/openssl-(version).tar.gz mv openssl-(version) openssl-(version)-i686 cd openssl-(version)-i686/ 3) Build OpenSSL. For 32-bit Windows: ./Configure \ --cross-compile-prefix=i686-w64-mingw32- \ --openssldir=/opt/openssl-mingw mingw shared make sudo make install sudo cp ms/applink.c /opt/openssl-mingw/include/openssl/ For 64-bit Windows: ./Configure \ --cross-compile-prefix=x86_64-w64-mingw32- \ --openssldir=/opt/openssl-mingw64 mingw64 shared make sudo make install sudo cp ms/applink.c /opt/openssl-mingw64/include/openssl/ 4) Download and unpack stunnel-(version).tar.gz. 5) Configure stunnel: cd stunnel-(version) ./configure 6) Build Windows 32-bit and/or 64-bit executables: cd src make mingw make mingw64 Building stunnel from source with MinGW (optional): Building on a Windows machine is possible, but not currently supported. Building stunnel from source with Visual Studio (optional): TODO Installing stunnel: 1) Run installer to install the precompiled binaries, or copy the stunnel.exe or tstunnel.exe executable located in the /stunnel-(version)/bin/mingw/ directory into the destination directory on a Windows machine, and copy OpenSSL DLLs: libeay32.dll, libssp-0.dll and ssleay32.dll into the same directory, if necessary. 2) Read the manual (stunnel.html). 3) Create/edit the stunnel.conf configuration file.