Upgrading from Rails 2.3.8 to 4.0

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This is a multi-step process, and depending on the size of your application, it can take a long time. At each step, you’ll want to test your application for bugs and problems and broken gems (because they are most certainly going to crop up). I have included links for the most complicated steps. Here is the path of least pain:

Update to Rails 2.3.18.

Update to Ruby 1.9.3.

Update to Rails 3.0.

Update to Rails 3.1.

Update to Rails 3.2.latest.

Update to Ruby 2.0.latest.

Update to Rails 4.0.

Update from Rails 4.0 to Rails 4.1.

Update from Rails 4.1 to Rails 4.2.

Update from Rails 4.2 to Rails 5.0.

Update from Rails 5.0 to Rails 5.1.

Bonus: If you have a large application, this is going to take a long time. If you have a large team, long-running branches become a huge headache because of recurring merge conflicts. One strategy for mitigating this is to dual boot your application with both versions of Rails so that you can have the new version running on your master branch, rather than on a long-running branch of its own.

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