Unable to require openssl when initialling rails - ruby-on-rails

Question

I have the error below when installing rails on osx maverick. OpenSSL has been installed already. Does anyone know how to fix this issue?
$ gem install rails
ERROR: While executing gem ... (Gem::Exception)
Unable to require openssl, install OpenSSL and rebuild ruby (preferred) or use non-HTTPS sources

Answer 1

You may need to update your OpenSSL CA Bundle, per these instructions from chruby about Ruby 2.1.2 which state:
Install 2.1.2
Note: MRI 2.1.2 requires OpenSSL >= 1.0.1.
wget http://cache.ruby-lang.org/pub/ruby/2.1/ruby-2.1.2.tar.bz2
tar -xjvf ruby-2.1.2.tar.bz2
cd ruby-2.1.2
./configure --prefix=/opt/rubies/ruby-2.1.2
make
sudo make install
Note: OS X users must update their OpenSSL CA cert bundle and properly set ./configure --with-opt-dir to compile against Homebrew's libraries:
wget http://cache.ruby-lang.org/pub/ruby/2.1/ruby-2.1.2.tar.bz2
tar -xjvf ruby-2.1.2.tar.bz2
cd ruby-2.1.2
./configure --prefix="$HOME/.rubies/ruby-2.1.2" --with-opt-dir="$(brew --prefix openssl):$(brew --prefix readline):$(brew --prefix libyaml):$(brew --prefix gdbm):$(brew --prefix libffi)"
make
sudo make install
For me, it was enough to just update my OpenSSL CA cert bundle via Homebrew and then reinstall Ruby using ruby-install
brew tap raggi/ale
brew install openssl-osx-ca
ruby-install ruby 2.1.2
After I performed the above steps, the issue stopped presenting itself.

Answer 2

For me... I had tried installing ruby 2.1.2 with ruby-install (since I use chruby for my ruby version manager). I had tried manually installing openssl with homebrew, etc. But I still couldn't get ruby-install to successfully build ruby 2.1.2. I've also had similar issues in the past with installing rubies and ruby-build worked then so I gave I gave it a shot here and it worked! As I understand it, ruby-build is the installer used by rbenv.
What I did was:
rm -rf ~/.rubies/ruby-2.1.2 (This is where my ruby installs are installed at.)
brew remove --force openssl
brew install ruby-build
restart console to be safe
ruby-build 2.1.2 ~/.rubies/ruby-2.1.2
And success! ruby-build seems to be much smarter than ruby-install at successfully installing weird dependencies. I'm done with ruby-install at this point -- it's given me too many problems! (brew remove --force ruby-install)

Answer 3

I've had a similar issue.
A fix to rvm was introduced just yesterday, and it was not yet merged with rvm master branch, so this is how you do it:
rvm get branch /bugfix/3923_set_osx_brew_openssl_compiler_config
rvm install 2.4.0
gem install rails
If that works for you, go to the issue and tell the developer how much you appreciate his effort:

Answer 4

Recently I was struggling with ruby installations due to the recent auto-update in openssl version from 1.0 to 1.1.
I found out that the ruby version < 2.4 does not work with openssl version > 1.0.
I was not even able to revert back the openssl to 1.0 version because other libs has dependencies on it.
No other solution except the one given below worked for me:
brew install rbenv/tap/openssl#1.0
rvm reinstall 1.9.3-p551 --with-openssl-dir='/usr/local/opt/openssl#1.0'
gem update --system
Now my ruby runs with openssl 1.0 whereas all other libraries are running on the default openssl version 1.1.

Answer 5

secure server is the reason of this issue. You can Install it by using this command:
gem install rails --source http://rubygems.org
by default its using https://rubygem.org as the source for the gem.
$ gem install rails ERROR: While executing gem ... (Gem::Exception) Unable to
require openssl, install OpenSSL and
rebuild ruby (preferred) or use non-HTTPS sources
so we can specify a source, http//:rubygems.org which is a non-HTTPS source.