conflicts Homebrew's OpenSSL and local LibreSSL

[lufia]

On my mac, Homebrew is installed at /opt/homebrew because /usr/local is used for other programs. And also, LibreSSL is installed at /usr/local.

In case of above, gem of Ruby that built with rbenv crashes:

$ rbenv install
ruby-build: use openssl from homebrew
Downloading ruby-2.6.0.tar.bz2...
-> https://cache.ruby-lang.org/pub/ruby/2.6/ruby-2.6.0.tar.bz2
Installing ruby-2.6.0...
ruby-build: use readline from homebrew
Installed ruby-2.6.0 to /Users/lufia/pkg/rbenv/versions/2.6.0

$ gem install bundle
dyld: lazy symbol binding failed: Symbol not found: _SSL_CTX_set_min_proto_version
  Referenced from: /Users/lufia/pkg/rbenv/versions/2.6.0/lib/ruby/2.6.0/x86_64-darwin18/openssl.bundle
  Expected in: flat namespace

dyld: Symbol not found: _SSL_CTX_set_min_proto_version
  Referenced from: /Users/lufia/pkg/rbenv/versions/2.6.0/lib/ruby/2.6.0/x86_64-darwin18/openssl.bundle
  Expected in: flat namespace

SSL_CTX_set_min_proto_version is declared in LibreSSL's /usr/local/include/openssl/ssl.h, but Homebrew's OpenSSL don't have.

I tried to build ruby without ruby-build:

$ cd ruby-2.6.0
$ CFLAGS='-I/opt/homebrew/opt/openssl/include' make

Then, gem don't crash.

How to do give priority to /opt/homebrew/opt/openssl/include ?

[mislav]

You can try something like

RUBY_CONFIGURE_OPTS="--with-openssl-dir=`brew --prefix openssl`" rbenv install 2.6.0

However, the ruby-build: use openssl from homebrew line of output in what you reported above suggests that ruby-build tried to use that openssl dir automatically. I'm not sure what exactly is the problem here.

[lufia]

I tried RUBY_CONFIGURE_OPTS=... but result still crash.

If /usr/local/include/openssl is not exist, then rbenv install builds correct binary.

$ cd /usr/local/include
$ sudo mv openssl _openssl
$ rbenv install 2.6.0
$ gem install bundle
Fetching bundle-0.0.1.gem
Successfully installed bundle-0.0.1
Parsing documentation for bundle-0.0.1
Installing ri documentation for bundle-0.0.1
Done installing documentation for bundle after 0 seconds
1 gem installed

[hsbt]

How to do give priority to /opt/homebrew/opt/openssl/include ?

Use or google DYLD_LIBRARY_PATH.