Upgrading OpenSSL ----------------- I. Additional Requirements 1) Install perl and nasm from Cygwin. If necessary, add the bin directory to end of %PATH%. It has to be at the end so that link.exe comes before /usr/bin/link. PATH=%PATH%;C:\cygwin\bin II. Compiling OpenSSL from source 2) Grab and extract the latest sources from openssl.org 3) Create C:\OpenSSL for installation mkdir C:\OpenSSL 4) Open the Visual Studio 2013 Developer Command Prompt 5) cd to the OpenSSL source directory 6) Configure OpenSSL perl Configure --prefix=C:\OpenSSL VC-WIN32 ms\do_nasm.bat Note #1: The slash after the C: in the configure line is significant Note #2: You can safely ignore "Compilation failed" messages from do_ms 6a) Configure OpenSSL to build with DEP, ASLR, and SAFESEH: perl -pi -e "s|/debug|/NXCOMPAT /DYNAMICBASE /SAFESEH| if /^LFLAGS/" ms\ntdll.mak 7) Compile and Install OpenSSL nmake -f ms\ntdll.mak install III. Making OpenSSL available to Nmap 8) Copy C:\OpenSSL over /nmap-mswin32-aux/OpenSSL. rsync -rvC --delete /cygdrive/c/OpenSSL/ nmap-mswin32-aux/OpenSSL/ Note #1: The trailing slashes/ are important to rsync! Note #2: You should do this from within cygwin because rsync gets confused with drive letter syntax.