Windows 10 MSYS2 openssl-3.4.0 "LoadError - The specified procedure could not be found."

[andrewngo]

Not able to require 'openssl' on Windows after updating the MSYS2 openssl library. I'm able to install it and I see the openssl.so file but it still doesn't run.

Packages (18) bsdtar-3.7.7-1  curl-8.10.1-1  gawk-5.3.1-1  info-7.1.1-1  libcurl-8.10.1-1  libexpat-2.6.3-1
              libgnutls-3.8.7-1  liblzma-5.6.3-1  libnghttp2-1.64.0-1  libopenssl-3.4.0-1  libreadline-8.2.013-1
              libsqlite-3.46.1-1  msys2-keyring-1~20241007-1  msys2-launcher-1.5-2  nano-8.2-1  ncurses-6.5.20240831-2
              openssl-3.4.0-1  xz-5.6.3-1

Packages (1) mingw-w64-x86_64-openssl-3.4.0-1

ruby -ropenssl -e 'puts OpenSSL::OPENSSL_VERSION'
>>
<internal:C:/Ruby32-x64/lib/ruby/site_ruby/3.2.0/rubygems/core_ext/kernel_require.rb>:85:in `require': 127: The specified procedure could not be found.   - C:/Ruby32-x64/lib/ruby/gems/3.2.0/gems/openssl-3.2.0/lib/openssl.so (LoadError)
        from <internal:C:/Ruby32-x64/lib/ruby/site_ruby/3.2.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
        from C:/Ruby32-x64/lib/ruby/gems/3.2.0/gems/openssl-3.2.0/lib/openssl.rb:13:in `<top (required)>'
        from <internal:C:/Ruby32-x64/lib/ruby/site_ruby/3.2.0/rubygems/core_ext/kernel_require.rb>:85:in `require'
        from <internal:C:/Ruby32-x64/lib/ruby/site_ruby/3.2.0/rubygems/core_ext/kernel_require.rb>:85:in `require'

Computer info

 ruby -v
ruby 3.2.3 (2024-01-18 revision 52bb2ac0a6) [x64-mingw-ucrt]

gem list openssl

*** LOCAL GEMS ***

openssl (3.2.0, default: 3.1.0, 3.0.1)

[System.Environment]::OSVersion.Version

Major  Minor  Build  Revision
-----  -----  -----  --------
10     0      20348  0

[MSP-Greg]

Try using mingw-w64-ucrt-x86_64-openssl. You listed mingw-w64-x86_64-openssl, which is the wrong package for Ruby 3.2.3, which shows x64-mingw-ucrt...

[andrewngo]

Both seem to be installed. Is there a way to force the package?

I use these commands to install it

call %ruby_dir%\bin\ridk exec pacman -Sy
call %ruby_dir%\bin\ridk install 2 3

and then pacman shows the following:

C:\tools\msys64\usr\bin\pacman.exe -Q | findstr openssl

libopenssl 3.4.0-1
mingw-w64-ucrt-x86_64-openssl 3.4.0-1
mingw-w64-x86_64-openssl 3.4.0-1
openssl 3.4.0-1

C:\tools\msys64\usr\bin\pacman.exe -Ss | findstr openssl
clangarm64/mingw-w64-clang-aarch64-openssl 3.4.0-1
clangarm64/mingw-w64-clang-aarch64-python-pyopenssl 24.2.1-2
mingw32/mingw-w64-i686-openssl 3.4.0-1
mingw32/mingw-w64-i686-python-pyopenssl 24.2.1-2
mingw64/mingw-w64-x86_64-openssl 3.4.0-1 [installed]
mingw64/mingw-w64-x86_64-python-pyopenssl 24.2.1-2
ucrt64/mingw-w64-ucrt-x86_64-openssl 3.4.0-1 [installed]
ucrt64/mingw-w64-ucrt-x86_64-python-pyopenssl 24.2.1-2
clang32/mingw-w64-clang-i686-openssl 3.4.0-1
clang64/mingw-w64-clang-x86_64-openssl 3.4.0-1
clang64/mingw-w64-clang-x86_64-python-pyopenssl 24.2.1-2
msys/libopenssl 3.4.0-1 (libraries) [installed]
msys/openssl 3.4.0-1 [installed]
msys/openssl-devel 3.4.0-1 (development)
msys/openssl-docs 3.4.0-1

[MSP-Greg]

I could repro the issue.

I haven't been in OpenSSL for a few months. It appears that OpenSSL 3.4 and 3.3 have some differences.

If I rename the OpenSSL dll's in Ruby's bin/ruby_builtin_dlls folder and copy the OpenSSL dlls from MSY2's ucrt64/bin into the Ruby folder, ruby -ropenssl -e 'puts OpenSSL::OPENSSL_VERSION works and shows OpenSSL 3.4.0 22 Oct 2024.

If you don't want to copy the dlls, you can get the OpenSSL 3.3.x packages from https://repo.msys2.org/mingw/ucrt64/. You'll have to uninstall Ruby OpenSSL 3.2.0 and reinstall it.