[ruby-core:110842] [Ruby master Bug#19115] OpenSSL fails to autoload (macOS)

["alanwu (Alan Wu)" <noreply@ruby-lang.org>]

Issue #19115 has been updated by alanwu (Alan Wu).


I've submitted a [PR](https://github.com/ruby/ruby/pull/6756) to fix this issue and I thought I'd also post some updates.

Here is a script to summarize the mechanics of the bug:

```ruby
puts RUBY_DESCRIPTION # ruby 3.2.0dev (2022-01-20) [wasm32-wasi]

autoload :Ripper, 'ripper' # can resolve to ripper.so, which is builtin
p [autoload?(:Ripper), defined?(Ripper), Object.const_defined?(:Ripper)]
# => [nil, nil, false]

# Compare with a library that's an .rb file
autoload :Abbrev, 'abbrev' # can resolve to ripper.so, which is builtin
p [autoload?(:Abbrev), defined?(Abbrev), Object.const_defined?(:Abbrev)]
# => ["abbrev", "constant", true]
```

It's specific to builds configured with `--with-static-linked-ext`.
Since WASM builds use this option you can reproduce the issue in a browser!

https://try.ruby-lang.org/playground/#code=puts+RUBY_DESCRIPTION+%23+ruby+3.2.0dev+(2022-01-20)+%5Bwasm32-wasi%5D%0A%0A%23+Setup+an+autoload+for+a+constant+to+load%0A%23+a+statically+linked+extension%0Aautoload+%3ARipper%2C+'ripper'+%23+can+resolve+to+ripper.so%2C+which+is+builtin%0Ap+%5Bautoload%3F(%3ARipper)%2C+defined%3F(Ripper)%2C+Object.const_defined%3F(%3ARipper)%5D%0A%23+%3D%3E+%5Bnil%2C+nil%2C+false%5D%0A%0A%23+Compare+with+a+library+that's+an+.rb+file%0Aautoload+%3AAbbrev%2C+'abbrev'+%23+can+resolve+to+ripper.so%2C+which+is+builtin%0Ap+%5Bautoload%3F(%3AAbbrev)%2C+defined%3F(Abbrev)%2C+Object.const_defined%3F(%3AAbbrev)%5D%0A%23+%3D%3E+%5B%22abbrev%22%2C+%22constant%22%2C+true%5D&engine=cruby-3.2.0dev

For native builds, the issue impacts RubyGems can make it think OpenSSL
is unavailable even though it is. The error is the same as mentioned in [Bug #18876]:

```
ERROR:  While executing gem ... (Gem::Exception)
    OpenSSL is not available. Install OpenSSL and rebuild Ruby (preferred) or use non-HTTPS sources
```

Also, some corrections for my mistakes in [Bug #18876].
I thought `defined? AutoloadConst` would trigger loading but it's supposed
to behave more like checking whether loading is necessary.
I also thought the issue was fixed on master but it was actually due to me
not including Ripper in my test build which made `ripper` resolve to `ripper.rb`
when the issue could only reproduce with `.so` features like `ripper.so` that are statically linked.


----------------------------------------
Bug #19115: OpenSSL fails to autoload (macOS)
https://bugs.ruby-lang.org/issues/19115#change-100198

* Author: thomthom (Thomas Thomassen)
* Status: Open
* Priority: Normal
* ruby -v: 3.1.2, 3.2.0dev
* Backport: 2.7: UNKNOWN, 3.0: UNKNOWN, 3.1: UNKNOWN
----------------------------------------
Related discussion: https://bugs.ruby-lang.org/issues/18876

We are seeing OpenSSL failing to autoload with the Ruby build we've been using. (We first observed this when using `Gem.install` that relies on autoload of OpenSSL). Our last working build was Ruby 2.7.2 with similar config.

This causes RubyGems' `HAVE_OPENSSL` constant to be incorrectly initialized, and subsequent calls to `Gem.install` fails. There might be other scenarios that fail as a result of that, but we've not managed to identified that.

```
 module Gem
   HAVE_OPENSSL = defined? OpenSSL::SSL # :nodoc:
```

Our Ruby 3.1.2 config:

```
'--prefix=/Users/user/.conan/data/ruby/3.1.2/sketchup/stable/build/bd95825b99dcb274d0e577fbdc953653a9ea0fb9' 
'--with-openssl-dir=/Users/user/.conan/data/openssl/1.1.1q/sketchup/stable/package/93ae0b0e7eebe0611c04d3e0d9bbf49fbce92332' 
'--with-libyaml-dir=/Users/user/.conan/data/libyaml/0.2.5/sketchup/stable/package/a56a950abed2e10dbdc26845400f0a034d97c454' 
'--disable-install-doc' 
'--disable-install-rdoc' 
'--enable-shared' 
'--enable-load-relative' 
'--with-static-linked-ext' 
'--without-debug' 
'--without-gdbm' 
'--without-gettext' 
'--without-irb' 
'--without-mkmf' 
'--without-rdoc' 
'--without-readline' 
'--without-tk' 
'--bindir=${prefix}/bin' 
'--sbindir=${prefix}/bin' 
'--libexecdir=${prefix}/bin' 
'--libdir=${prefix}/lib' 
'--includedir=${prefix}/include' 
'--oldincludedir=${prefix}/include' 
'--datarootdir=${prefix}/share' 'cflags=-mmacosx-version-min=10.14 -fdeclspec' 'cxxflags=-mmacosx-version-min=10.14 -fdeclspec' 'LDFLAGS=-mmacosx-version-min=10.14 -fdeclspec'
```

We also tested with latest build from master (November 8th 2022):

```
./ruby -ve 'p RbConfig::CONFIG["configure_args"]'
ruby 3.2.0dev (2022-11-07T19:35:21Z master b14f133054) [x86_64-darwin20]
" '--prefix=/Users/vmehta/ruby/ruby-master/' '--with-openssl-dir=/Users/vmehta/.conan/data/openssl/1.1.1q/sketchup/stable/package/f2d937af1fa19d5fc4095849a65d1927e9e75ae7/' '--with-libyaml-dir=/Users/vmehta/.conan/data/libyaml/0.2.5/sketchup/stable/package/3fc084e254210603a5c5aece184b2d45e2509b30' '--disable-install-doc' '--disable-install-rdoc' '--enable-shared' '--enable-load-relative' '--with-static-linked-ext' '--without-debug' '--without-gdbm' '--without-gettext' '--without-irb' '--without-mkmf' '--without-rdoc' '--without-readline' '--without-tk'"
```

Using an RVM of Ruby 3.1.2 this appear to work as expected. But using out configuration, that we've used for the Ruby 2.x versions are now failing. We haven't been able to figure out the reason for this.



-- 
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