<p>Upgrading a Rails application is one of those things that always sounds simple in theory: update your Gemfile, run a few commands, and you’re done.</p>
<p>But if you’ve actually gone through a Rails upgrade like me, you know it’s rarely that straightforward.</p>
<p>My first real attempt at a major upgrade taught me some lessons the hard way, and I wish I had known a few things before diving in. Hopefully, this article can save you some of the frustration I went through.</p>
<h2>1. It’s Not Just About the Rails Version</h2>
<p>When people talk about a Rails upgrade, it often sounds like a single step: moving from Rails 6 to Rails 7, or soon, from Rails 7 to Rails 8. But the truth is, upgrading Rails is less about the framework itself and more about the entire ecosystem around your app.</p>
<p>Gems, database drivers, front-end dependencies - all of these have to play nicely together with your chosen Rails version. I learned quickly that Rails version compatibility is a puzzle you can’t ignore. You might have one outdated gem that blocks the entire upgrade until you either update it, replace it, or fork it.</p>
<h2>2. Small Steps Beat Giant Leaps</h2>
<p>My biggest mistake was trying to jump directly from Rails 5.2 to Rails 7 in one go. Spoiler: it didn’t work. Too many things had changed in between, and I spent more time untangling errors than making progress.</p>
<p>What I wish I had done instead: follow a proper <a href="https://www.railsup.io/blogs/the-ultimate-rails-upgrade-guide-for-2025?utm_source=community&amp;utm_medium=organic&amp;utm_campaign=traffic" target="_blank" rel="noopener nofollow">Rails upgrade guide</a> that recommends upgrading version by version. Going from 5.2 → 6.0 → 6.1 → 7.0 might sound tedious, but it keeps the process manageable. Each step introduces smaller, more understandable changes, and you can run tests in between to make sure nothing breaks.</p>
<h2>3. Tests Are Your Best Friend (Or Worst Enemy)</h2>
<p>If you have a good test suite, a Rails upgrade feels challenging but doable. Without tests, you’re walking blind. My early upgrade attempt lacked enough test coverage, and I kept wondering whether the app was really stable after fixing an error.</p>
<p>Before starting any upgrade, I recommend shoring up your test suite. Even basic integration tests can give you peace of mind. That way, when you bump the Rails version and rerun tests, you’ll immediately know where things broke.</p>
<h2>4. Gem Compatibility Is the Hidden Boss Level</h2>
<p>The single biggest source of headaches? Gems. Some of them weren’t maintained anymore, others hadn’t been updated for newer Rails versions, and a few had subtle changes that caused weird bugs in production.</p>
<p>I spent hours searching through GitHub issues to figure out if a gem was safe to use with Rails 7. What I didn’t know back then is that tools like <a href="https://www.railsup.io/?utm_source=community&amp;utm_medium=organic&amp;utm_campaign=traffic" target="_blank" rel="noopener nofollow">RailsUp</a> exist to scan your Gemfile and flag potential compatibility problems before you even start upgrading. Having that visibility upfront saves a ton of time and frustration.</p>
<h2>5. Documentation Isn’t Just for Beginners</h2>
<p>I used to think I didn’t need to read release notes closely. Big mistake. The Rails team does a great job documenting breaking changes, deprecations, and new features in every release.</p>
<p>For example, Rails 7 introduced changes around encrypted attributes and default configurations that would have been easier to handle if I had read the docs first. Instead, I stumbled into them one by one. Now, whenever I plan a Rails upgrade, I make it a point to read the official release notes and even skim community upgrade guides to see what others have run into.</p>
<h2>6. Downtime and Rollback Planning Matter</h2>
<p>During my first upgrade attempt, I deployed to production without a rollback plan. Unsurprisingly, something broke, and I spent a frantic night patching things. Lesson learned: always plan for rollback.</p>
<p>Set up feature flags, deploy to staging, and make sure you can revert quickly if things go sideways. A Rails upgrade isn’t just a development task, it’s also about protecting your users from unnecessary downtime.</p>
<p>Despite the challenges, my experience of upgrading to Rails 7 was worth it. Performance improvements, Hotwire, and better defaults made the effort worthwhile. The app felt more modern, and we were in a better position to adopt Rails 8 when it arrives.</p>
<p>But what I wish I had realized earlier is that the Rails upgrade process isn’t just about chasing new features - it’s about keeping your app healthy and future-proof. Every version you skip only makes the eventual upgrade harder.</p>
<h2>Takeaway</h2>
<p>If you’re preparing for a Rails upgrade, here’s the short version of what I wish I knew:</p>
<ul>
<li>
<p>Upgrade step by step, don’t skip versions.</p>
</li>
<li>
<p>Strengthen your test suite before you start.</p>
</li>
<li>
<p>Check <a href="https://www.railsup.io/?utm_source=community&amp;utm_medium=organic&amp;utm_campaign=traffic" target="_blank" rel="noopener nofollow">Rails version compatibility</a> for all your gems.</p>
</li>
<li>
<p>Read the release notes like your upgrade depends on it (because it does).</p>
</li>
<li>
<p>Always have a rollback plan.</p>
</li>
</ul>
<p>Upgrading Rails can feel overwhelming at times, but it doesn’t have to be a nightmare. With the right preparation, the process can be smooth, and you’ll end up with a faster, more secure, and future-ready application.</p>
<p><a href="https://app.daily.dev/manofthematch" data-mention-id="xILwaA6T9reJWtElo1Tw7" data-mention-username="manofthematch" translate="no">@manofthematch</a></p>


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Rails upgrades require careful planning and incremental steps rather than jumping versions. Key considerations include gem compatibility checks, comprehensive test coverage, reading release notes thoroughly, and having rollback plans. The process involves upgrading the entire ecosystem, not just Rails itself, with tools available to scan for compatibility issues before starting.

What I Wish I Knew Before Rails Upgrade #ruby #rails