Rishi Giri
Downgrading Ruby
[ ruby , openssl , downgrade , problem , fix ]

Due to massive procrastination, I was stuck with Ubuntu 16.04 LTS for a while, but I switched to Mint 21.2 a few days ago. There was a bit of a rush, so I didn’t think much about trying another OS before switching, and there’s no way I was going to get stuck in the world of snap packages, so I chose Mint over Ubuntu. I was using an older version of Ruby (>2.7) on my system, but since Ruby doesn’t fall under my domain of work, and everything was centered around building my website using Jekyll, I never encountered any issues. Until now.

I’m using the Parchment Theme for this site, and everything was working perfectly on the old machine. However, when I switched to Mint and started working, I faced a series of issues. I didn’t note down anything, and I’m not feeling motivated enough to reproduce the issue, so I’m going to write what I remember and what worked.

Phase Uno — Basics

$ git clone git@github.com:rhl-bthr/parchment.git
$ cd parchment
$ bundle install

el problema – Bundler could not find compatible versions for gem "bundler":

To fix –

$ gem install bundler -v '~> X.Y.Z'
$ bundle _X.Y.Z_ install

I think I faced some issues here which I don’t remember clearly; possibly, it couldn’t force RubyGems to use the version which bundle _X.Y.Z_ install specified.

I possibly deleted the Gemfile.lock and ran bundle install, and that might have worked. I’m not entirely sure because I do not exactly remember, so moving forward.

Phase Dos — Panic Findings

When I did

$ bundle exec jekyll serve

I got -

jekyll 3.9.0 | Error:  no implicit conversion of Hash into Integer
/home/rishi/.local/share/gem/ruby/3.0.0/gems/pathutil-0.16.2/lib/pathutil.rb:502:in `read': no implicit conversion of Hash into Integer (TypeError)
        from /home/rishi/.local/share/gem/ruby/3.0.0/gems/pathutil-0.16.2/lib/pathutil.rb:502:in `read'

Two things –

After googling, here are a few things I found out:

source "https://rubygems.org"

gem "jekyll"
gem "webrick"
gem "pathutil", github: "sdogruyol/pathutil", ref: '6ab144a7706c2bc5fa0dfdfa498e94ff66e944c6'

Applying patch locally -

sudo sed -i.bak 's/, kwd/, **kwd/' $(gem which pathutil)

Phase Tres — Copying Pasting

A few things that I did within a couple of minutes.

Phase Cuatro — Forgetting

  1. I forgot about one of the solutions, which was to not use the plain global Jekyll version 4. So, my Gemfile had gem 'jekyll', '4.0.0' instead of gem "jekyll", github: "jekyll/jekyll".

  2. I also forgot to add gem "pathutil", github: "sdogruyol/pathutil", ref: '6ab144a7706c2bc5fa0dfdfa498e94ff66e944c6' to my Gemfile.

As of now, I can’t say whether these approaches would have fixed the problem while I was trying out various things, but the first point is part of the solution, which I implemented last after downgrading Ruby.

Phase Cinco — RVM Clashes

Downgrading Ruby turned out to be a massive pain in the ass because I first chose rvm, which brought tons of issues.

$ rvm install 2.7.2

Now, I don’t remember in what order I faced these issues, but they all arrived.

The issue was that it couldn’t build the old Ruby versions because they relied on OpenSSL 1.1.1, whereas newer versions of Ubuntu come with OpenSSL 3.x. The approach to solve Problem 2 failed in my case, but many people mentioned that it worked for them.

None of the solutions worked because things were falling apart during compilation. I was tired at this point, so I purged the entire Ruby ecosystem from my machine. I removed rvm, rbenv, ruby-build, asdf, chruby, and ran apt purge ruby. It made me feel better, but after the purge, the urge to fix things was not over.

Phase Seis — Going For A Walk

It was already 4 am, so I decided to go for a walk. On my way back home, I stumbled upon this blog post. If only I had read the comments on this Stack Overflow post earlier, I might have found the solution sooner. But who reads everything when they’re tired and just want to fix things as soon as possible? Not me.

I installed rbenv, which seems to be the best out of all the Ruby version managers.

The setup was fairly simple -

$ git clone https://github.com/rbenv/rbenv.git ~/.rbenv

$ ~/.rbenv/bin/rbenv init

$ FPATH=~/.rbenv/completions:"$FPATH"
$ autoload -U compinit
$ compinit

Since I didn’t want to go through more frustration, especially since people still faced issues downgrading Ruby using rbenv, as mentioned here. Even though one of the maintainers commented that -

Update: newer versions of ruby-build work around the problem of the user having to manually download and install the required version of OpenSSL.
What this means when installing, for example, Ruby 2.7.5 on Ubuntu 22.04 is that ruby-build will automatically download and compile OpenSSL 1.1 and link Ruby to that instead of to the system OpenSSL.
Make sure to upgrade your ruby-build!

I decided to follow the steps mentioned in this blog post. It didn’t have any explanation, but I’ll provide details on each command for clarity:

$ wget https://www.openssl.org/source/openssl-1.1.1w.tar.gz
$ tar zxvf openssl-1.1.1w.tar.gz

$ export OPENSSL=$HOME/.openssl/openssl-1.1.1w

$ cd openssl-1.1.1w
$ ./config --prefix=$OPENSSL --openssldir=$OPENSSL

  1. --prefix=$OPENSSL — Specifies the installation directory for OpenSSL.

  2. --openssldir=$OPENSSL — Specifies where OpenSSL will store its configuration files and certificates.

$ make
$ make test
$ make install

$ rm -rf $OPENSSL/certs

$ ln -s /etc/ssl/certs $OPENSSL/certs

$ RUBY_CONFIGURE_OPTS=--with-openssl-dir=$OPENSSL rbenv install 2.7.8

The RUBY_CONFIGURE_OPTS variable specifies the options to pass to the ruby build process, and --with-openssl-dir=$OPENSSL tells ruby to use the OpenSSL installation in the directory specified by the OPENSSL variable, which we set previously.

Make sure, you’ve gem "jekyll", github: "jekyll/jekyll" in your Gemfile. That’s it.


Cheers :beer: