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by Daniel Berger.
Original Post: Building openssl for Ruby with Visual Studio
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Yet another "how to build" post mostly for my own reference, but you may find it useful.
Building the openssl lib for Ruby with Visual Studio is a bit of a pain. First, you'll need to install openssl itself (which you can build from source if you have Perl installed) or use their precompiled stuff. To build openssl itself from source, do this:
This assumes a 32-bit build, but you get the idea. Once that's done, you'll need to cd to the ext/openssl directory of wherever your Ruby source code is. Before you begin you will need to hand edit the extconf.rb file and change line 40 from "if $mingw" to "if File::ALT_SEPARATOR". This ensures that the gdi and wsock32 libs are linked properly.
With that done, run "ruby extconf.rb --with-openssl-dir=c:/usr/local", or wherever you installed openssl. Once that's complete you have to pause again and hand edit the generated Makefile because it's missing a declaration for $(top_srcdir). Look near the bottom and you'll see this line:
Then run "nmake" followed by "nmake install". Once that's done you can test it out by firing up irb and typing 'require "openssl"' to ensure you don't get an error.
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