Issue #13080 has been updated by Nobuyoshi Nakada.


From https://bugs.ruby-lang.org/attachments/6316/bad_mkmf_2.4.log#L229, your ssl library has references to GDI32.dll. I'm not sure why rand_win.c needs it though.
Probably you need `--with-openssl-config` option for a proper pkg-config file.

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Bug #13080: [mingw regression] broken openssl extension in 2.4.0p0
https://bugs.ruby-lang.org/issues/13080#change-62293

* Author: Jon Forums
* Status: Open
* Priority: Normal
* Assignee: 
* Target version: 
* ruby -v: ruby 2.4.0p0 (2016-12-24 revision 57163) [i386-mingw32]
* Backport: 2.2: UNKNOWN, 2.3: UNKNOWN, 2.4: UNKNOWN
----------------------------------------
When building using slightly modified rubyinstaller build recipes and a msys2/mingw64-6.2.0 (32bit) toolchain, the build fails to create the openssl extension when using openssl 1.0.2j or 1.1.0c.

~~~
$ ruby --version
ruby 2.4.0p0 (2016-12-24 revision 57163) [i386-mingw32]
$ ruby -ropenssl -e "puts OpenSSL::OPENSSL_VERSION"
C:/Users/Jon/Documents/RubyDev/ri-git/sandbox/ruby21_mingw/lib/ruby/2.4.0/rubygems/core_ext/kernel_require.rb:55:in `require': cannot load such file -- openssl (LoadError)
        from C:/Users/Jon/Documents/RubyDev/ri-git/sandbox/ruby21_mingw/lib/ruby/2.4.0/rubygems/core_ext/kernel_require.rb:55:in `require'
~~~

Attached are the failing openssl mkmf.log and Makefile files from the 2.4.0p0 build.

I can provide good versions of the files from a 2.3.3p224 x32 build using openssl 1.0.2j if needed.

---Files--------------------------------
bad_mkmf_2.4.log (21.9 KB)
bad_Makefile_2.4 (6.22 KB)


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