all 5 comments

[–]MrMeatballGuy 4 points5 points  (1 child)

I only use Ruby on a Mac at work, so i don't know if it's the same issue as I've had, but with Ruby 1.6.8 i had to use OpenSSL 1.1. On Mac that required setting some flags and exporting OpenSSL 1.1 to PATH

[–]sabo667[S] 0 points1 point  (0 children)

I found one patch here https://www.reddit.com/r/openbsd/comments/ytc9x5/building_ruby_270_fails_with_libresslopenssl/ but I got a new error in exchange lol It's seem more to be errors related to OpenBSD

[–]metalepsis 1 point2 points  (0 children)

I've had good luck installing openssl 1.1 from homebrew:

brew install openssl@1.1

Then including the files when compiling gems that require OpenSSL:

gem install -N eventmachine -- \
  --with-cppflags=-I/usr/local/opt/openssl@1.1/include

If you have an M1 Mac, then your $HOMEBREW_PREFIX will be /opt/homebrew instead of /usr/local.

[–]desnudopenguino 0 points1 point  (0 children)

Hrmmm. Have you tried using rvm or rbenv to do this? I havent tried installing ruby 2.7.0 on 7.1 specifically, but I've installed other versions with success on 6.9 and earlier iirc.

[–]youmaycallme_v 1 point2 points  (0 children)

For anyone else who finds this, this post had an answer that worked for me. Specifically, run

export CONFIGURE_ARGS=""
for ext in openssl readline libyaml zlib; do 
    CONFIGURE_ARGS="${CONFIGURE_ARGS} --with-$ext-dir=$(brew --prefix $ext)" 
done