Jekyll openssl and webrick errors after upgrading to Ruby 3

• Table of Contents

Goal

After setting up the blog after a long break, I installed the latest ruby 3.0.1 locally and ran bundle install, only to be greeted with a pile of errors. I'm documenting the errors I encountered in hopes it helps others trying to install Jekyll in a modern environment.

Approach

This post is written for users who already have a basic understanding of Jekyll project setup or have previously completed an installation.

Tools used

• rvm
• ruby 3.0.1
• zsh
• bundle
• jekyll

Error 1

In file included from binder.cpp:20:
./project.h:119:10: fatal error: 'openssl/ssl.h' file not found
#include <openssl/ssl.h>
        ^~~~~~~~~~~~~~~
1 error generated.
make: *** [binder.o] Error 1

make failed, exit code 2

Gem files will remain installed in /Users/kahlo/.rvm/gems/ruby-3.0.1/gems/eventmachine-1.2.7 for inspection.
Results logged to /Users/kahlo/.rvm/gems/ruby-3.0.1/extensions/x86_64-darwin-20/3.0.0/eventmachine-1.2.7/gem_make.out

An error occurred while installing eventmachine (1.2.7), and Bundler cannot continue.
Make sure that `gem install eventmachine -v '1.2.7' --source 'https://rubygems.org/'` succeeds before bundling.

Fix

1. brew reinstall openssl

   The first result I found while searching suggested that openssl might be installed incorrectly.

2. Set the PATH — reference link

   Configuring the PATH for openssl was suggested as another solution.

3. gem install eventmachine -- --with-openssl-dir=/usr/local/opt/openssl@1.1

   This last approach is what worked for me. Installing the eventmachine gem while explicitly pointing it to the openssl directory lets it install cleanly. After that, run bundle install or bundle update.

Error 2

~/.rvm/gems/ruby-3.0.1/gems/jekyll-4.2.0/lib/jekyll/commands/serve/servlet.rb:3:in `require': cannot load such file -- webrick (LoadError)

I thought everything was installed and ran bundle exec jekyll serve — only to hit an error saying webrick was missing.

Fix

bundle add webrick

webrick needs to be installed separately because it was removed from Ruby's default bundled gems starting with Ruby 3.0.0.

Result

Installation complete

After getting everything sorted, I was able to run bundle exec jekyll serve and bring up the Jekyll blog locally. Coming back to blogging after a long time apparently requires a cold-sweat tax. Ha.

References

• eventmachine github issue
• jekyll 실행 시킬 때 `require': cannot load such file -- webrick (LoadError) 오류가 난다면