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.

[andrewngo]

Thanks. I copied libcrypto-3-x64.dll and libssl-3-x64.dll and that unblocks me for now. Appreciate it!

[rhenium]

I noticed our CI builds with Ruby 3.2 and 3.3 have been broken with a similar error message. Could this be the same issue?

https://github.com/ruby/openssl/actions/runs/11578248737/job/32231644029

C:/hostedtoolcache/windows/Ruby/3.2.5/x64/bin/ruby.exe -I./lib -ropenssl.so [...]
[...]
ruby 3.2.5 (2024-07-26 revision 31d0f1a2e7) [x64-mingw-ucrt]
<internal:C:/hostedtoolcache/windows/Ruby/3.2.5/x64/lib/ruby/3.2.0/rubygems/core_ext/kernel_require.rb>:38:in `require': 127: The specified procedure could not be found.   - D:/a/openssl/openssl/lib/openssl.so (LoadError)
	from <internal:C:/hostedtoolcache/windows/Ruby/3.2.5/x64/lib/ruby/3.2.0/rubygems/core_ext/kernel_require.rb>:38:in `require'
rake aborted!

However, builds with Ruby master don't share the issue even with OpenSSL 3.4.0:

rubyinstaller2: https://github.com/ruby/openssl/actions/runs/11578248737/job/32231645011
ruby-loco/ucrt: https://github.com/ruby/openssl/actions/runs/11578248737/job/32231645466

ruby 3.4.0dev (2024-10-28 master 83568a41af) +PRISM [x64-mingw-ucrt]
OpenSSL::OPENSSL_VERSION: OpenSSL 3.4.0 22 Oct 2024
OpenSSL::OPENSSL_LIBRARY_VERSION: OpenSSL 3.4.0 22 Oct 2024

[MSP-Greg]

@rhenium

Could this be the same issue?

Yes, it is. Both MSYS2 and MSFT/vcpkg have updated to OpenSSL 3.4.0.

CI is compiling with 3.4.0, but loading 3.3.z dll's. I don't recall seeing a 'policy' statement re OpenSSL 3.y compatibility. Is this a bug in 3.4.0? IIRC, in the past, one could compile with 3.3, and the code would run with 3.2 dlls.

To fix this will require some work in setup-ruby.

Also, is this a Windows specific issue? Obviously, the issue is related to Windows builds including their dll files.

[rhenium]

CI is compiling with 3.4.0, but loading 3.3.z dll's. I don't recall seeing a 'policy' statement re OpenSSL 3.y compatibility. Is this a bug in 3.4.0? IIRC, in the past, one could compile with 3.3, and the code would run with 3.2 dlls.

Using a newer OpenSSL version at run time than the compile time is supported, as long as the major version number matches, which is "1.0", "1.1", or "3" for OpenSSL, but downgrading likely isn't.

https://github.com/openssl/general-policies/blob/fa7152227fb5f6b576f78f5197fcd2c401bf029b/policies/versioning-policy.md#minor-release

I haven't been able to reproduce it locally, but if it's what's happening here, it seems like the problem.

Also, is this a Windows specific issue? Obviously, the issue is related to Windows builds including their dll files.

Other CI builds in ruby/openssl should be using the same OpenSSL installation for compiling and testing.

[MSP-Greg]

Did some more testing. Both Puma & EventMachine compile ext code with OpenSSL. They both passed CI where the Ruby under test bundled 3.3 dlls, but the ext was compiled with 3.4 files.

Puma passed with Ruby master builds (all 3.4), but EventMachine failed.

The issue was with OpenSSL::X509::Request#version=. With OpenSSL 3.3, the values 0, 1, and 2 are accepted. With OpenSSL 3.4, only 0 works. I verified this with the tests in test/openssl/test_x509req.rb.

Also, is this a Windows specific issue? Obviously, the issue is related to Windows builds including their dll files.

Other CI builds in ruby/openssl should be using the same OpenSSL installation for compiling and testing.

Yes. That gets rather messy. I don't recall every trying it on macOS or Ubuntu...

[rhenium]

Both Puma & EventMachine compile ext code with OpenSSL. They both passed CI where the Ruby under test bundled 3.3 dlls, but the ext was compiled with 3.4 files.

I think it can happen to work, but nothing guarantees it.

I suspect this is the change causing it to break for ruby/openssl (though I didn't actually verify it - I just found it by git diff openssl-3.3.0 openssl-3.4.0 include/openssl): https://github.com/openssl/openssl/blob/openssl-3.4.0/include/openssl/evp.h#L574

ruby/openssl uses EVP_MD_CTX_size(). In 3.4.0 header, it's redirected to a new function called EVP_MD_CTX_get_size_ex() which doesn't exist in 3.3 or earlier.

The issue was with OpenSSL::X509::Request#version=. With OpenSSL 3.3, the values 0, 1, and 2 are accepted. With OpenSSL 3.4, only 0 works. I verified this with the tests in test/openssl/test_x509req.rb.

This is separate and is due to a behavior change (a stricter error checking) in OpenSSL 3.4. ruby/openssl also had to fix a test case affected by this in #747.