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Limping Along With Octopress and Catalina macOS

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I am still using the Octopress 2 framework for the website. This has been challenging as the dependencies for old obsolete software gets harder and harder to satisfy. However, it appears that I have succeed again for at least the Catalina release of macOS.

I found out I had a problem when I went to fix Disqus which had moved to https:// protocol. I found the files named disqus.html which had http:// and changed it to https:// but I was unable to regenerate the code due to a failure of the Octopress tool to run.

I use

chruby ruby-2.2.10

due to the yajl-ruby which won’t build under later rubies.

My already built ruby-2.2.10 would not run because the openssl 1.0 version that had been linked in had disappeared (either due to Catalina or my migration to a new MacBook Pro.) Rebuilding ruby with

ruby-install ruby-2.2.10

did not work nor did

ruby-install ruby-2.2.10 -- --with-openssl-dir=/usr/local/opt/openssl

did not work since the openssl was version 1.1.

After a fair bit of false steps, the successful approach was built around Chris Hobb’s December 3, 2019 solution (for RVM) posted on Stack Overflow.

First follow his steps (repeated here) to install openssl 1.0.2 by downloading openssl 1.0.2 from, and then building and installing it with

tar -xzf openssl-1.0.2t.tar.gz
cd openssl-1.0.2t
./Configure darwin64-x86_64-cc --prefix=/usr/local/opt/openssl@1.0
make test
sudo make install

and then adapting to chruby / ruby-install approach, build ruby 2.2.10

ruby-install ruby-2.2.10 -- --with-openssl-dir=/usr/local/opt/openssl@1.0

Then going to the directory where I have the blog system and having previously deleted Gemfile.lock, I re-ran the install of gems into the vendor directory.

bundle install

Of course, in making this post, I issue

bundle exec rake new_post["Limping along with Octopress and Catalina macOS"]

Catalina has moved to using zsh instead of bash for its default shell. Having taken the plunge, I found out that square brackets are used differently in zsh. I was able to escape them to continue working:

bundle exec rake new_post\["Limping along with Octopress and Catalina macOS"\]

Thanks to Qihuan Piao for this hint.

One less groan

Evidently the version of pigments used does not know about zsh so the code blocks have to be marked as bash instead of zsh.

Time to think about a supported framework. Perhaps a migration to the modern version of Jekyll or a broader research into other static site tools that allow markdown content.