I have been using Octopress since 2012, and it works fine for me in all these years. But unfortunately the project has been abandoned since January 2015, which means it depends on a lot of legacy packages, and misses a lot of fancy new features. For example, the version I was using depends on jekyll-0.11.2, while jekyll-4.0.0 was already released in August 2019.

Although I don’t bother using the legacy software and was satisfied with the feature set as long as it’s working, setting up a new environment for the legacy software becomes harder and harder. On macOS, I need to use rbenv to compile and install a specific Ruby version for Octopress: Ruby at 1.9.3-p392. As the version is very old, when using Apple’s latest compiler (Apple clang version 11.0.0) or other GCC versions which are available on HomeBrew (I have tried GCC-4.9 and GCC-9), there are warnings during compilation (see this GitHub issue for an example warning), which ensures a failed installation.

$ rbenv install 1.9.3-p392
Downloading yaml-0.1.4.tar.gz...
-> http://dqw8nmjcqpjn7.cloudfront.net/36c852831d02cf90508c29852361d01b
Installing yaml-0.1.4...
Installed yaml-0.1.4 to /usr/local/opt/rbenv/versions/1.9.3-p392

Downloading ruby-1.9.3-p392.tar.gz...
-> http://ftp.ruby-lang.org/pub/ruby/1.9/ruby-1.9.3-p392.tar.gz
Installing ruby-1.9.3-p392...

BUILD FAILED

Inspect or clean up the working tree at /var/folders/mx/mfxgb8450d97ssnd588_bg980000gn/T/ruby-build.20130222110749.98264...