Ruby on Rails developer to maintain a Mastodon-based community app (ongoing)

Overview We run The Highlander, a local community news and reading app for a rural community in Ontario, Canada. It is a fork of Mastodon, the open-source social platform, adapted into an unfederated local reading experience. The developer who built it has moved on (amicable - he had a full time job offer). We are looking for someone to take over: first to get the app onto a supported, patched version, then to keep it running and healthy on an ongoing basis. This is not a from-scratch build. It is maintenance and stewardship of an existing Rails codebase with custom changes on top. That is the skill we are hiring for. The app The custom work on top of Mastodon includes: An all-reader home feed: public posts go to active readers rather than relying on the follow graph No federation or ActivityPub network behaviour An installable PWA Content categories, with reader-facing category filters and opt-in category push notifications A custom Poster role and category-management permissions for admins Custom onboarding, branding, and email copy The stack Ruby on Rails: core app, REST API, admin UI, background jobs PostgreSQL, Redis, Sidekiq Node.js streaming API React and Redux frontend Deployed with Docker Compose on a managed VM (Elestio), auto-deployed from a GitHub branch Where things stand We would rather be straight with you than have you discover this in week one: The fork is on Mastodon 4.6.0-alpha.1 and has never been synced with upstream since development started in November 2025. It is a pre-release alpha and has none of the upstream security patches from the last eight months. There are no scheduled backups. We have a verified manual snapshot off the server (database, media, secrets) and a backup script in the repo, but nothing automated and no tested restore. The previous developer had full production access. We may want the production secrets rotated, and we want your read on whether that is worth the disruption. The repo is documented reasonably well: README, development setup, and an operations doc covering a production incident we have already had. We will share it with shortlisted candidates. First project A defined piece of work to start, so we both find out how this goes before committing to anything ongoing: Configure proper scheduled backups Restore our existing backup into a clean environment and prove the app comes up. We have never tested it. Bring the app onto a current, supported, patched Mastodon release without breaking our custom features Document what you did, and what state you found things in Item 2 first: it is quick and it closes our worst risk. Ongoing after that Track upstream Mastodon security releases and merge them into the fork Respond when the app breaks Monthly health check Occasional small features. We expect to want some in roughly three months, but the near-term job is stability, not new work. What you need Required: Strong, demonstrable Ruby on Rails experience Real experience working inside a large existing codebase, ideally an open-source fork. You will be spending more time reading code than writing it. Solid Docker and Docker Compose, and comfort on a Linux server. Our worst production incident so far was an infrastructure problem, not an app problem. Rails skill alone is not enough. PostgreSQL, and an understanding of Redis and Sidekiq beyond basic CRUD Ability to explain technical decisions in plain language. We are not developers. Nice to have: Mastodon experience specifically PWA, service worker, and web push Enough React and Redux to work on the frontend What we are not looking for Please do not apply if your plan is to rebuild the app from scratch or move it off Mastodon. We are not doing that at this stage. To apply Tell us: Your experience maintaining a fork, or working inside a large codebase you did not write. Be specific: what was it, what did you do. In two or three sentences, how you would approach merging an upstream Mastodon security release into a fork that carries custom modifications. What goes wrong, and how do you handle it. Your hourly rate and rough weekly availability. Start your reply with the word "Highlander" so we know you read this. Shortlisted candidates will get our operations documentation and a short paid trial task before we commit to anything.