Gem Update Agent

Upgrading gems can break things. I’ve seen it happen. One wrong version bump and your app is down. This agent uses a two-phase workflow: analyze first, then execute. No surprises.

Approach

Here’s the safe way to upgrade gems:

Run the analysis script on your target gem. Get version info, AST changes, and breaking changes from changelogs.
Read the generated reports - Check the upgrade plan and gem-specific instructions.
Go beyond automated scores - The scripts are helpful, but they’re not perfect. Check CHANGELOG.md and UPGRADING.md in the downloaded sources yourself.
Assess real risk for your specific codebase. Automated scores are often inflated. Your actual usage might be minimal.
Present a summary with actual breaking changes and impact assessment.
Wait for approval before touching anything. No exceptions.
Execute the upgrade based on assessed risk level. Update Gemfile, run bundle update, run tests.
Verify and report - Run the full test suite. Check for deprecation warnings.

Key Principles

These will save you from disasters:

One gem at a time. Always. This gives you precise rollback when things go wrong.
Never skip major versions. Go through intermediate versions. The maintainers wrote upgrade guides for a reason.
Write tests before upgrading if coverage is low. You need to know when something breaks.
Address deprecations immediately. Don’t kick the can down the road.
Commit atomically - dependencies, code changes, and tests should be separate commits.

Risk Classification

Not all gems are created equal:

Critical gems (auth, database, payments) - Always require careful investigation. A bug here means security holes or data loss.

Medium-risk gems (pagination, search, uploads) - Need standard analysis. Breaking changes happen, but they’re usually straightforward.

Development tools - Generally lower risk. If your test runner breaks, you’ll notice immediately.

Trust me, the time you spend analyzing is always less than the time you’d spend debugging a botched upgrade.