Legacy Rescue & Rails Upgrades
Un-stick a stalled Rails app — upgrade it, pay down the debt, and make it safe to ship again.
Legacy Rescue & Rails Upgrades gets a stalled Rails app moving again: version upgrades, dependency and security remediation, test-coverage backfill, and performance work — done in small, reviewable steps, never a big-bang rewrite. It's for teams stuck on an old Rails version, buried in tech debt, or afraid to deploy an app that still makes money. It's led by an engineer with 15+ years of software experience and 13+ years of Rails specifically — the person who's spent a career keeping production Rails safe to ship.
What problem does this solve?
The app makes money, and nobody wants to touch it. You're pinned to an old Rails version, the dependencies throw security warnings, the test suite is thin or red, and every deploy is a gamble someone would rather not take. The team works around the codebase instead of in it. You've been quoted a rewrite — expensive, risky, and a year where nothing new ships. What you actually need is to make the app you already have safe to change again, without betting the business on a from-scratch gamble.
How we approach it
1. Diagnose first — a real read of the codebase: version gap, dependency and security risks, test coverage, and the slow spots. 2. Stabilize the ground — backfill tests around the code we're about to touch, so change is safe. 3. Upgrade incrementally — Rails and Ruby moved forward in small, reviewable steps, each one shippable on its own. 4. Remediate — dependencies and known vulnerabilities, N+1s and slow queries. 5. Hand back an app you can deploy on a Friday. No big-bang rewrite, ever — the app keeps running and earning the whole time.
What you get
- A written assessment: current version, the upgrade path, risks, and priorities - Rails and Ruby version upgrades, done in reviewable increments - Dependency updates and security-vulnerability remediation - Test-coverage backfill around the code being changed - Performance fixes — N+1 queries, slow endpoints, database bottlenecks - Incremental modernization toward current Rails conventions - An app that's safe to deploy again — and a clear path for what's next
How long does it take?
Best started with a Diagnostic audit to map the work, then incremental fixed-scope steps or an ongoing retainer — your call. Never a big-bang rewrite.
Make it safe to ship again
Some apps aren't broken — they're frozen. They still make money, but the team is afraid to deploy, the Rails version is years behind, and the dependencies light up with warnings. A rewrite feels like the only way out, and it's the most expensive, riskiest one.
There's a better path: modernize the app you already have, in small reviewable steps, until you can deploy it on a Friday without holding your breath.
The credibility behind the work
This offering doesn't lean on a case study — it leans on a career.
Fifteen-plus years shipping software. Thirteen-plus years of Rails specifically, dating back to when RSpec and Cucumber were the daily tools for TDD and BDD. A full arc from Senior Engineer to Web Architect to Engineering Manager to Head of Engineering at a fintech — IOU Financial, ranked #14 in American Banker's Best Places to Work in Fintech 2025. Modernizing and stewarding production Rails at scale is the throughline: engineering roles at Adobe (Dynamic Tag Management), Box, Popmenu, and Manheim (Cox Automotive) — the kind of large, long-lived codebases where careful upgrades and paying down debt is the job.
Legacy rescue is a whole category among the shops we admire — it's FastRuby's entire business, and an explicit line at Test Double, BigBinary, and Planet Argon. It's real, in-demand work, and it's squarely in the wheelhouse of someone who's spent a career keeping production Rails healthy.
No big-bang rewrites
The method is deliberately unglamorous: diagnose, stabilize with tests, upgrade one reviewable step at a time, remediate the security and performance problems, and hand back an app that's safe to change. The app keeps running and earning the whole time. You never bet the business on a year-long rewrite that might not land.
How the engagement runs
The best starting point is a Diagnostic — a fixed-fee audit that maps the version gap, the risks, and the upgrade path, so you know the shape of the work before committing to it. From there it's incremental, fixed-scope steps, or an ongoing retainer if you'd rather we stay on and keep the app current for good.
Frequently asked questions
- How old is too old? Can you upgrade a really out-of-date app?
- Old is normal for this work — that's the whole point. We move the app forward one reviewable step at a time rather than jumping versions blindly, so even a large gap is a series of safe increments instead of one terrifying leap. The Diagnostic tells us exactly what the path looks like before you commit.
- Why not just rewrite it?
- Because a rewrite means a year where nothing new ships, a working app thrown away, and every old bug rediscovered the hard way. Your app already knows things about your business that no spec captures. We modernize what works and pay down what doesn't — in small steps — so it keeps earning the whole time.
- Who's actually doing this work?
- A senior engineer with 15+ years shipping software and 13+ years of Rails specifically — and a full leadership arc from Senior Engineer to Web Architect to Head of Engineering at a fintech (IOU Financial, #14 in American Banker's Best Places to Work in Fintech 2025). Stewarding production Rails at scale — at Adobe, Box, and Cox Automotive — is exactly this work. TDD/BDD discipline from the start.
- How do you keep upgrades from breaking things?
- Tests first. Before touching code, we backfill coverage around what we're about to change, so a regression shows up in CI instead of in production. Every upgrade lands as a small, reviewable change you can ship and verify on its own — not one giant merge you have to take on faith.
- Do you offer this as ongoing help, or just a one-time fix?
- Either. Some teams want a focused, fixed-scope upgrade and then to take it from there; others want us to stay on and keep the app current. That's what OctaneCare is for — ongoing maintenance, security updates, and the next upgrade before it becomes an emergency.
Ready to talk about Legacy Rescue & Rails Upgrades?
Tell us about your project and we'll help you figure out the right starting point.