Migrating From Octopress 2 to Octopress 3

I recently upgraded this blog to Octopress 3, as part of rebuilding (and Docker-ifying) my blog Jekyll build environment. This post is a guide of my upgrade experience and to talk about various workarounds I needed to make to get everything working.

Introduction to Octopress 3

With Octopress 2, the paradigm I used was to fork the canonical Octopress Git repository and maintain all my posts and theme files as a branch forked off of the Octopress "master" branch. I then periodically ran git merge octopress/master to pull upstream core Octopress infrastructure changes into my custom branch.

As mentioned in the official "Octopress 3.0 Is Coming" announcement, there were various downsides to the Octopress 2 paradigm. The main pain-point revolves around how Octopress 2 is basically just the skeleton of a Jekyll blog that you need to fork and modify – which means that when you want to take upstream changes of the Octopress 2 infrastructure, you need to merge those upstream changes into your local forked branch and work through any merge-conflicts. Sometimes easy, sometimes time-consuming.

With Octopress 3, all of this has been re-thought so that your site is a Jekyll site first-and-foremost and all the extra Octopress "goodies" are delivered via gems which can be used as Jekyll plugins. That creates a nice clean separation between your site content versus the Jekyll site-building tools. Neat!

Octopress 3 is Dead, Long Live Octopress 3 …?

Side note: it's unclear what the future of Octopress 3 is.

Octopress 3 development was active and vibrant circa 2015, but all the activity in the Octopress plugin repositories seemed to tail-off towards the beginning of 2016. It's a shame, but I understand how these things sometimes go – priorities change, and life comes first.

I opted to embrace Octopress 3 as-is because I was a big Octopress 2 fan and I really like the Octopress 3 vision. Also, I wanted the small quality-of-life features which Octopress added above-and-beyond the default Jekyll scaffolding.

But I did run into some small bumps along the way – more on that later.

Setup Docker

I created a docker-compose.yml file to compartmentalize Jekyll build environment:

version: '3'
image: jekyll/jekyll:latest
BUNDLE_PATH: /srv/bundle
- 4000:4000
- .:/srv/jekyll
- data-bundle-cache:/srv/bundle

Some key points:

  • Use the standard jekyll/jekyll:latest Docker image.
  • Use a persistent Docker volume as the $BUNDLE_PATH to avoid needing to re-download and re-install all the Gemfile gems for each docker-compose run container.

Using Docker containers means everything is compartmentalized and that it's easy to bootstrap my blog build environment onto another machine. Containers for the win.

Setup a New (Octopress 3-Flavored!) Jekyll Site

Create a new directory for your brand-new Jekyll site:

$ mkdir blog
$ cd blog

Copy your docker-compose.yml file into the new directory.

Use docker-compose run to start a shell into a new Docker container:

$ docker-compose run --rm --service-ports jekyll /bin/sh

Install the Octopress gem:

# gem install octopress
Fetching: titlecase-0.1.1.gem (100%)
Successfully installed titlecase-0.1.1
Parsing documentation for octopress-3.0.11
Installing ri documentation for octopress-3.0.11
Done installing documentation for titlecase, octopress-deploy, octopress-hooks, octopress-escape-code, redcarpet, octopress after 1 seconds
6 gems installed

Use the octopress new command to create a new Octopress-flavored Jekyll site:

$ octopress new -f .
Running bundle install in /srv/jekyll...
Bundler: Don't run Bundler as root. Bundler can ask for sudo if it is needed, and
Bundler: installing your bundle as root will break this application for all non-root
Bundler: users on this machine.
Bundler: The dependency tzinfo-data (>= 0) will be unused by any of the platforms Bundler is installing for. Bundler is installing for ruby but the dependency is only for x86-mingw32, x86-mswin32, x64-mingw32, java. To add those platforms to the bundle, run `bundle lock --add-platform x86-mingw32 x86-mswin32 x64-mingw32 java`.
Bundler: Fetching gem metadata from https://rubygems.org/...........
Bundler: Fetching version metadata from https://rubygems.org/..
Bundler: Fetching dependency metadata from https://rubygems.org/.
Bundler: Resolving dependencies...
Bundler: Fetching public_suffix 3.0.0
Bundler: Installing public_suffix 3.0.0
Bundler: Using bundler 1.15.3
Bundler: Fetching jekyll 3.5.1
Bundler: Installing jekyll 3.5.1
Bundler: Fetching jekyll-feed 0.9.2
Bundler: Installing jekyll-feed 0.9.2
Bundler: Fetching minima 2.1.1
Bundler: Installing minima 2.1.1
Bundler: Bundle complete! 4 Gemfile dependencies, 22 gems now installed.
Bundler: Bundled gems are installed into /srv/bundle.
New jekyll site installed in /srv/jekyll.
Added Octopress scaffold:
+ _templates/
+ draft
+ page
+ post

(Tip: You'll need to pass the -f flag to octopress new because you're trying to install into a directory which already exists)

Edit the Gemfile (created during octopress new) and minimally add the baseline Jekyll and Octopress gem dependencies:

source "https://rubygems.org"
gem 'jekyll'
group :jekyll_plugins do
gem 'octopress'

At this point, you have a brand-new empty Jekyll site with a few extra Octopress-flavored bits (like the _templates directory), and you can run normal Jekyll commands like 'jekyll serve', jekyll build, etc.

Managing Jekyll Plugin Gems

Jekyll supports several ways of managing gem-based plugins.

I opted to manage all my gem plugins via a Bundler group in the Gemfile file. This just seemed the most straight-forward approach. It also seemed like a good idea to track both the Gemfile file and counterpart Gemfile.lock file via source-control (e.g. Git), but your mileage may vary.

There are several neat Octopress 3 gem plugins, but I found that several of the plugins didn't work out-of-the-box with Jekyll 3.x (because most of the plugins haven't been maintained in over a year now). But thanks to the community-effect of GitHub, several other folks have fixed the Jekyll incompatibility problems and submitted pull requests. You can install the patched version of the various Octopress 3 gems by specifying an explicit git: remote URL (and the specific branch:) for that particular gem in your Gemfile.

Here is the final Gemfile I ended-up with, with various patched Octopress gems:

source "https://rubygems.org"
gem 'jekyll'
group :jekyll_plugins do
gem 'jekyll-paginate'
gem 'jekyll-redirect-from'
gem 'jekyll-sitemap'
gem 'octopress'
gem 'octopress-code-highlighter', git: 'https://github.com/randycoulman/code-highlighter.git', branch: 'handle-multiline-spans' # Fix for multi-line <span>'s (gh:octopress/code-highlighter #8)
gem 'octopress-codeblock'
gem 'octopress-codefence', git: 'https://github.com/mkleucker/codefence.git', branch: 'fix-warning-deprecated' # Fix Jeykll 3 compatibility (gh:octopress/codefence #17)
gem 'octopress-image-tag'
gem 'octopress-ink', git: 'https://github.com/iphoting/ink.git', branch: 'jekyll-3' # Fix Jekyll 3 compatibility (gh:octopress/ink #65)
gem 'octopress-linkblog', git: 'https://github.com/andrewdavidbell/linkblog.git', branch: 'jekyll3' # Fix Jekyll 3 compatibility (gh:octopress/linkblog #7)
gem 'octopress-quote-tag', git: 'https://github.com/NickTomlin/quote-tag.git', branch: 'master' # Fix Jeykll 3 compatibility
gem 'octopress-solarized'

Migrating Content

You'll need to copy over whatever parts you need from your old Octopress 2 site to your new Octopress 3 site:

  • Copy all your posts: source/_posts -> _posts
  • Copy all your other pages
  • Copy all your images: source/images -> images
  • Copy any theme files: source/_includes -> _includes, etc, etc.

Installing a Theme

The original Octopress 2 theme was baked into the Octopress 2 git branch.

You could probably migrate over the old Octopress 2 theme from your old Octopress 2 site, but now that we're using plain-vanilla Jekyll 3 that means we can use any of the plethora of Jekyll-based themes. So I went hunting for a new theme.

I ended-up choosing the Pixyll theme because it was clean and modern.

I "installed" the Pixyll theme by:

  1. Cloning the Pixyll theme from its GitHub repo to a separate directory.
  2. Manually copying over the files I wanted from the Pixyll directory into my Octopress 3 site.
  3. Tracking the pristine Pixyll theme files in a baseline commit.
  4. Personalizing the theme files as I wanted.

I opted to create a "baseline" commit of the Pixyll theme (along with making note of what Git revision # from the Pixyll repo I was forking at) to (in theory) make it easier to take and review upstream changes to the Pixyll git branch: create a local Git branch off that baseline commit, copy in any upstream changes to the Pixyll theme, and then git merge forward onto my local master branch and work through any merge conflicts.

Here are some of the customizations & personalizations I made along the way:

  • Updated _config.yml to set various site flags which the Pixyll theme respects.
  • Updated _includes/footer.html to include my name and copyright.
  • Updated _includes/head.html to add the {% css_asset_tag %} Liquid tag, which was needed to get the octopress-solarized plugin to take effect (via the octopress-asset-pipeline plugin).
  • Various tweaks to CSS styling.


Here are some helpful posts which laid out the vast majority of the migration process:

Happy upgrading!