[ruby-core:109044] [Ruby master Bug#18876] OpenSSL is not available with `--with-openssl-dir`

Issue #18876 has been updated by alanwu (Alan Wu).

Status changed from Open to Feedback

Since `bundle-env ruby -ropenssl` works, I suspect it has something to
do with `--env-shebang`. Maybe the `gem` command isn't running with
the Ruby you want. Try running `RUBYOPT=-v bundle-env gem` and
comparing that with `ruby -v` (without `bundle-env`). You might
also want to try `RUBYOPT=-vd` to surface any errors while loading
OpenSSL; it looks like RubyGems loads it using an `autoload`:
https://github.com/rubygems/rubygems/blob/master/lib/rubygems/openssl.rb

----------------------------------------
Bug #18876: OpenSSL is not available with `--with-openssl-dir`
https://bugs.ruby-lang.org/issues/18876#change-98192

* Author: Gloomy_meng (Gloomy Meng)
* Status: Feedback
* Priority: Normal
* ruby -v: 3.1.1
* Backport: 2.7: UNKNOWN, 3.0: UNKNOWN, 3.1: UNKNOWN
----------------------------------------
i try use ruby + gem in my macos app with .a framework, i need install ruby in a custom location.
so i make & make install openssl with this configure:
``` shell
/usr/bin/perl Configure --prefix="......./local/dependencies" no-shared zlib darwin64-x86_64-cc
```

then make & make install ruby with this configure:
``` shell
/bin/sh configure --prefix /Users/xxxxx/xxxx/local/bundle --with-openssl-dir="/Users/xxxxx/xxxx/local/dependencies" --enable-load-relative --with-static-linked-ext --disable-install-doc --with-out-ext="xxxxxx"
```

------

because i need to isolated environment, so i make `bundle-env` file for run shell. and i uploaded bundle-env file 

------

and update gem by local

``` shell
destroot/bundle/bin/bundle-env gem install downloads/rubygems-update-3.3.15.gem --no-document --env-shebang
```

at last, run install alway got exception: 
``` shell
destroot/bundle/bin/bundle-env gem install xxxxxxx --version="xxxxxx" --no-document --env-shebang
ERROR:  While executing gem ... (Gem::Exception)
    OpenSSL is not available. Install OpenSSL and rebuild Ruby (preferred) or use non-HTTPS sources
```

at the same env, i tried some command, and i got the right version what i make install 

``` shell
destroot/bundle/bin/bundle-env ruby --version     // ruby 3.1.1p18 (2022-02-18 revision 53f5fc4236) [x86_64-darwin21]
destroot/bundle/bin/bundle-env gem --version      // 3.3.15
destroot/bundle/bin/bundle-env ruby -ropenssl -e 'puts OpenSSL::OPENSSL_VERSION'   // OpenSSL 1.1.1i  8 Dec 2020

```

------
i found and uploaded `ext/openssl/mkmf.log` and 




---Files--------------------------------
bundle-env (852 Bytes)
mkmf.log (215 KB)


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