Remote Ruby

Jeff Dickey is back on Remote Ruby, and he's been busy! Andrew and Chris catch up with Jeff to discuss the latest improvements to mise, including precompiled Ruby builds, automatic tool updates, and dotfile management. Jeff also introduces some of his newest projects, including packslip, a new standard designed to make software distribution more secure, and jactionlint, his modernized GitHub Actions linter. The conversation explores everything from managing secrets with fnox and cleaning up m...

On this episode, Chris, Andrew, and David dive into the rapidly changing world of AI-assisted development, Ruby performance, and the future of building software. They kick things off with AI-powered coding workflows before exploring the Campfire benchmarking controversy and the exciting possibilities of Roundhouse, which could dramatically improve Ruby application performance. Andrew shares his experience launching a new AI agent inside Podia, including the challenges of getting its MCP integ...

Fresh off Rails World 2026, Chris, Andrew, David, and returning guest John Athayde unpack the surprisingly emotional conversation surrounding AI, Ruby, Rails, and the future of programming. What starts as a discussion about Spinel, Roundhouse, Rust, and Rails performance quickly turns into a much bigger question: what happens to developers when writing code is no longer the main job? They dig into AI-assisted development, changing ideas around craftsmanship and creativity, the growing importa...

Recorded live from Rails World 2026, Andrew, Chris, David, Jason Charnes, and eventually Andy Croll, unpack the strange mood surrounding this year’s conference. Much of the conversation centers on DHH’s keynote and the increasingly agent-driven future of software development: if AI can write, debug, and even understand the code for us, what happens to the value of frameworks, developer expertise, documentation, and even Ruby itself? They also dig into Hotwire, Active Search, Herb, Active Job ...

Andrew and Chris are back with a packed episode covering everything from Rails World anticipation and Rails 8.2 to security, Ractors, AI-assisted development, and some ambitious new Ruby tooling. They dig into RubyGems recent spam-publishing incident and Trusted Publishing, look at Shopify’s push toward Ractor-safe Rails, and explore Roundhouse, a project experimenting with compiling Rails applications into entirely different target languages. They also talk about using Claude for project pla...

Chris, Andrew, and David are back with a conversation that starts with Rails World plans. They break down APIs, webhooks, and persistent connections, using everything from thermostats to Stripe to explain how systems communicate and recover when things go wrong. From there, Chris shares what caught his eye in PlanetScale’s new Postgres sharding work, before the conversation shifts heavily toward AI-assisted programming, where the tools are surprisingly capable one minute and making baffling a...

Ryan Castillo returns to the show to catch everyone up on what’s changed since his last appearance…and a lot has changed. Ryan explains why he and his co-founder moved on from their web application firewall Wafris and built Knowatoa, a platform focused on helping companies understand how their brands appear in AI-powered search. From there, the conversation expands into GEO and AI search visibility, multi-agent coding workflows, AI skills as the future of content, and when developers should o...

This week, Chris, Andrew, and David dig into a packed mix of Rails news, developer tooling, and the increasingly complicated role AI is playing in everyday coding. They talk about Herb making its way into Rails, the realities of Rails upgrades and stacked PRs, new approaches to Git hosting and object storage, and how Rails is being evaluated in the age of AI agents. They also get into improvements coming to Action Text, Podia’s approach to “flavored” Markdown, the never-ending frustrations of...

Andrew and David catch up on everything from wild weather and the upcoming Rails World conference to Andrew’s latest deep dive into MCPs (Model Context Protocols). Andrew shares what he’s learned while building an MCP for a Rails side project, including choosing the official Ruby MCP SDK, discovering the limitations of resources versus tools, and wrestling with OAuth and Doorkeeper authorization. They also look ahead to Rails World in Austin, highlighting talks on Active Search, Ractors, Herb...

Ernesto Tagwerker joins Chris, Andrew, and David, to talk about how AI is changing Rails development, consulting, and the way teams approach upgrades and maintenance. They discuss using Claude Code for Rails upgrades, the risks of relying too heavily on AI-generated tests and code, and why strong development standards are becoming even more important. The conversation also explores code quality, open AI models, team consistency, and how developers can use AI to work more efficiently without g...

In this episode, Chris, Andrew, and David dig into their latest experiences building with Claude, from massive diffs and unnecessary view specs to the challenge of catching subtle mistakes in AI-generated code. Andrew shares what went into launching Podia’s new Shop experience, Chris breaks down a serious Rails Active Storage security vulnerability, and David earns a developer rite of passage by accidentally bringing production to its knees. Along the way, they talk Redis 6, smarter Active Re...

Irina Nazarova and Vladimir Dementyev from Evil Martians return to preview the second annual SF Ruby Startup Conference and share what they learned from bringing the event to life for the first time. They discuss the conference’s new focus on ambitious builders, the importance of creating meaningful connections for attendees, and why Ruby on Rails remains a powerful foundation for startups tackling difficult, real-world problems. The conversation also explores open-source innovation, AI-assis...

Chris, Andrew, and David begin with summer heat, home cooling problems, and an IPv6 issue preventing Andrew from playing Battlefield 6. The conversation quickly heads down a Raspberry Pi rabbit hole, with projects ranging from smart-home automation and MagicMirror dashboards to local AI transcription. David then recaps RubyConf in Las Vegas before the group discusses design patterns, the changing conference landscape, and how AI is reshaping programming education, software development, and th...

This week, Andrew and Chris swap stories from the front lines of Ruby development, from wrangling GitHub Actions and speeding up CI to keeping old Ruby versions alive on brand-new servers. They also unpack a tricky Sidekiq deployment issue, explore the promise of compiling Ruby apps into standalone executables, and reflect on how AI is making once-impossible infrastructure problems a little easier to solve. Hit download now to hear more! Links Chris Oliver XAndrew Mason BlueskyDavid Hill Link...

Chris, Andrew, and David dig into the practical realities of modern development, from building faster server images with Packer and untangling database schema problems to deciding when refactoring, code coverage, and quality tools are actually useful. They also share where AI coding assistants are saving real time, where they still create confusion, and why good judgment remains just as important as the tools themselves. The episode wraps with the conversation going completely off the r...

In this episode, Chris, Andrew, and David kick things off with a very Remote Ruby style detour through Costco, Blue Apron, leftovers, Blackstone grills, and cast iron pans. Then, Andrew explains his Stripe subscription migration scare and major GitHub Actions workflow improvements that sped up Podia’s CI by 20–30%. They dive into Apple’s new on-device AI tooling, container alternatives on macOS, and the state of conferences, GitHub, AI infrastructure costs, solar power, and even crows attacki...

Chris returns from Greece and catches up with Andrew and David on travel, conferences, movies, and the latest developments in the Rails community. They dig into the newly announced Rails World lineup, the possibilities of Active Search, alternatives to Elasticsearch, extending Action Text and Lexi, a tricky ruby-vips dependency update, and mise’s rapidly expanding machine bootstrap tools. They wrap up with open source funding, RubyConf preparations, rising tech prices, and the massive anticip...

Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter

Chris, Andrew, and David catch up after a missed week of recording and quickly dive into the kind of deeply practical Rails work that only comes from real production pain. Andrew shares the massive subscription and billing migration happening at Podia, including Stripe edge cases, legacy plan preservation, and stress-test tooling built from live scenarios. Chris then goes deep on a Hatchbox email cancellation flow that turns into a Rails internals rabbit hole around Action Mailer callbacks, m...

[This episode from February 2024 was never published and recently discovered] In today’s episode, Andrew kicks things off with a rant about tackling developer experience tasks at Podia, wrestling with GitHub actions, and Heroku deployment woes. Then the conversation takes a turn to the importance of debugging, the power of bash scripting, and the challenges of naming in programming, with Chris mentioning DHH’s insights from a live stream. They discuss Chris’s travel plans for RubyConf in Aust...

Chris and David cover a lot of ground in this episode, starting with Chris’s experience teaching a Rails workshop for Frontend Masters in Minneapolis. Along the way, they dive deep into Rails authentication, Devise, Authlogic migrations, Chris’s ReviseAuth gem, password security, session handling, and the hard tradeoffs of maintaining open source tools. The episode wraps with big podcasting news: David is taking over The Ruby on Rails Podcast! Hit download now to hear more! Links ...

Chris, Andrew, and David kick things off with a detour through Dungeon Crawler Carl, Rails World tickets, and conference travel before diving into developer tooling, package manager security, and the latest Ruby ecosystem updates. The conversation covers everything from Hotwire-style UI patterns and pnpm/Corepack setup to Jeff Dickey’s new package manager, the RubyGems malicious package attack, Ruby 4.0.4, Shopify’s Rubydex, Claude/Codex chatter, and the increasingly strange future of AI agen...

In this episode, Chris, Andrew, and David are back together with David starting out giving a recap of Blue Ridge Ruby and his renewed motivation to contribute to open source. The group discusses the value of smaller single-track conferences to hallway conversations, and lightning talks. The conversation then shifts into real-world Rails and Stripe lessons, including workshop prep, validation decisions, webhook recovery, subscription edge cases, and the growing complexity of payment integratio...

Chris and Andrew catch up after Andrew’s whirlwind “vacation-ish” road trip before diving into Stripe’s latest announcements, usage-based billing, merchant-of-record pricing, Rails file upload quirks, Active Storage image handling, Sidekiq queue strategy, and the future of RubyGems. They also discuss browser form behavior, preserving and deleting attachments, image variant performance, and how to think more clearly about background job priorities. Hit download now to hear more! Links Judoscal...

On this episode of Remote Ruby, Chris, Andrew, and David kick things off with dentist trauma, gold star stickers, and fiber internet. The conversation centers on Rails direct routes, why they can be more powerful than helpers, the upcoming Rails World CFP and ticket rush, how AI is becoming more practical inside real engineering teams, a reminder to fill out the Rails survey, and Chris’s continued work expanding the Rails Getting Started Guide into a more realistic e-commerce tutorial with wi...

Chris, Andrew, and David open with some classic confusion over what day it is then dive into Podia’s gradual rollout of a major new app version, including how the team is handling migration, feature flags, dogfooding, and eventual cleanup. From there, the discussion turns to underrated Rails routing features like direct routes and resolve routes, a newly merged Rails query command, observability improvements through Hatchbox’s AppSignal integration, and the ongoing pain of CSS build tooling i...

This BREAKING NEWS episode is a candid reaction to Ruby Central’s latest shakeup, with Chris, Andrew, and David unpacking leadership departures, financial strain, the cancelled gala, and what all of it says about the organization’s direction. The conversation moves beyond the headlines into bigger questions about trust, transparency, community values, conference strategy, RubyGems sustainability, and whether Ruby Central can rebuild credibility by involving more of the community in what happe...

Chris and David welcome guest John Athayde, who runs the branding and UX consultancy, Meticulous. They dive into John’s unusual path through the Rails world as a designer, front-end developer, consultant, author, and UX thinker. The conversation moves from early Rails history and The Rails View into a broader discussion about why designers need to understand implementation, how AI is changing product and UI work, where component-based design is headed, and why browser support is still one of ...

This episode of Remote Ruby opens with stories of exhaustion from a sleepless week. Then, Chris, Andrew, and David spend most of the episode unpacking two big themes: trust and governance in open source, and the growing mess of software security and AI-assisted development. They dig into the new Ruby Central write-up on the RubyGems/Bundler fracture and question whether it actually clarifies the path forward, then pivot into the Axios npm compromise, supply-chain risk, and how fragile modern ...

On this episode, Chris, Andrew, and David bounce from Ruby and Rails security updates into the messy realities of caching, UI architecture, and browser support. They break down the latest Zlib-related Ruby CVE, Dalli updates, Rails security and bugfix releases, and what maintenance windows mean in practice. Then, they swap stories about Redis, Memcached, observations about GitHub’s reliability amid massive Claude attributed code activity, and the kinds of performance problems that only show u...

Chris, Andrew, and David catch up on health, sleep deprivation, and the new Invincible season and Fallout. David shares some RubyConf CFP submissions news and this year’s broad conference themes. They discuss Andrew finishing difficult authentication work, touching on OAuth/SSO complexity and pricing, the idea of products built more for bots than humans, and where AI is proving useful, especially for debugging and research. The conversation eventually widens into a more skeptical look at the ...

On this episode, Andrew’s buried in messy authentication work spread across legacy code, Chris recounts a frustrating GitHub Actions debugging session, and David explains the mental drain of working across both Vue 2 and Vue 3 in the same application. They talk about using workflow run triggers, scheduled builds, and GitHub’s new Agentic Copilot workflows such as CI Doctor, Automatic Code Simplifier, and issue/PR management, while lamenting low-quality AI-generated PRs and paid AI code review...

Chris and David welcome back Adam McCrea from Judoscale, to discuss the uncertainty around Heroku after Salesforce’s announcement that it would stop taking new enterprise customers. Adam shares how the news landed in real time during a founder’s retreat, and the conversation expands into what Heroku’s apparent “maintenance mode” means for developers, pricing, autoscaling, platform alternatives, and the broader challenge of building durable developer businesses in the AI era. They also touch o...

Chris, Andrew, and David welcome special guest Jeff Dickey (jdx), creator of mise, discussing his background rewriting the Heroku CLI from Ruby to Node due to Ruby distribution/sandboxing issues. The conversation digs into why language CLIs are hard to distribute, the tradeoffs between shims vs PATH-based version switching, why tasks can be the “clean” solution, and Jeff’s Rust-first tooling philosophy. They also dive into his other projects: usage (CLI docs/completions), Pitchfork (dev...

Cameron Dutro returns to the show to introduce LiveComponent, a new library that adds client-side state and targeted re-rendering to Rails ViewComponent using Hotwire + Stimulus with minimal JavaScript. Chris, Andrew, and Cameron dig into why he built it, how it serializes component state and models, how updates flow from events to fast server-rendered HTML morphs, where it shines compared to plain Turbo/Stimulus, and how optional React support can help with migration and interoperability. Hi...

Andrew and David hold down the fort without Chris and catch up on what they’ve been watching and reading, before welcoming back Joe Masilotti, the show’s most listened to guest from last year. They talk about Hotwire Native’s momentum, why “Bridge Components” are the unlock for truly native features, Joe’s push toward SwiftUI compatibility, the messy reality of in-app purchases, and how his “PurchaseKit” aims to simplify the whole Apple/Google webhook maze. We also hear about Joe’s new podcas...

On this episode of Remote Ruby, Chris, Andrew, and David dive into the newly released Claude Opus 4.6 and share their frustrations and solutions for debugging a turbo stream issue in Rails. They discuss a range of debugging challenges they've faced, including Rails credentials decryption errors and handling unexpected URL parameters in Pagy. The conversation shifts to the Ruby Gala, a fundraising event tied to RubyConf, highlighting its purpose, structure, and some notable people being honore...

In this episode, Chris, Andrew, and David kick off with humorous stories about coding experiences across different languages, and then they welcome back guest Kevin Newton who shares his journey from Shopify to Meta. Then, Kevin discusses the intricacies of Ruby and Python, particularly the challenges and trade-offs in their runtime implementations. The conversation then shifts to the development and adoption of the Prism parser in Ruby, highlighting its impact on various projects. Lastly, Ke...

In this episode, Blue Ridge Ruby organizers Jeremy Smith and Joe Peck join Andrew, Chris, and David to talk about the conference returning in 2026. They explain why it’s different (single-track, long breaks, and memorable community activities), what they’ve learned from running it, and how folks can help (speaking, sponsoring, and attending). The discussion also highlights the importance of community and in-person interactions in the tech industry, offering insights into how these events supp...

In this episode, Chris, Andrew, and David dive into details about refactoring with SQL, updates on new Ruby versions, and share their views on various developer tools including Mise, Overmind, and Foreman. They also touch on standardizing tools within their teams, the benefits of using Mise for Postgres, and the efficiency of task scripts. The conversation also covers encoding issues, Basecamp Fizzy SSFR protection, and rich-text editors like Lexxy and its application in Basecamp. Additionall...

In this episode of Remote Ruby, Chris, Andrew, and David have conversations from New Year's resolutions and monitor specifications, to the sustainability challenges of open source projects like Tailwind CSS. They discuss the pros and cons of various hardware, upgrading to Ruby 4.0, recent issues in software projects, and the evolving landscape of AI's impact on productivity tools. They also touch on gaming experiences with Arc Raiders and the never-ending monitor hunt. Hit download now to hea...

In this episode of Remote Ruby, Chris, Andrew, and David humorously discuss the rapid increase of 'wrapped' features in various apps, recount personal experiences with food apps, and then dive into their favorite conference moments of the year. They also explore the concept of UI affordances and its importance in web design and give a preview of upcoming conferences in 2026, and a brief discussion on modern CSS and JavaScript elements. Hit download now to hear much more! Links Chris Oli...

Chris, Andrew, and David are back together, and the conversation starts out with TV talk, Fallout hype, why some shows overstay their welcome (Prison Break), and the “season one magic” problem (Reacher). Then there’s a big shoutout to Marco’s Rails Luminary win, and a deep dive into AI rabbit holes: self-hosting LLMs, Mac minis, and the looming reality of both token costs and RAM shortages. They discuss the Ruby releases (3.4.8 + Ruby 4.0 preview3), highlighting practical fixes, previewing fe...

In this episode, Chris and David Hill catch up on wild winter temperature swings, then dive into what Chris has been refactoring in Jumpstart to reduce merge pain, cut dependencies, and make upgrades smoother. The conversation branches into AI-assisted coding pitfalls and where AI shines, new web security headers that could simplify CSRF handling, and a promising new “old school Heroku on steroids” platform from Evan Phoenix called Miren, plus a few Hatchbox deployment learnings along the way...

Chris and Andrew kick things off with some weather whiplash and snowblower talk before introducing a new guest on the show, long-time Rubyist David Hill. They chat about fast food and favorite shows, David’s accidental path into Ruby and Rails, and various projects he’s worked on, including an AED management application. The discussion also touches on the new open-source release of Basecamp's Kanban board, Fizzy, and some innovative CSS techniques used in the project. The conversation wraps u...

Andrew kicks off at 8 a.m. with six Docker containers running, and he and Chris dive into what modern Rails development looks like inside dev containers—covering Rails’ own images and features, using Mise and Playwright instead of Selenium, and why OrbStack has replaced Docker Desktop on their Macs. They talk through the trade-offs of running services in containers, the quirks of Kamal’s new local registry, and how Chris is turning all of this into a practical SaaS building series that shows ...

Andrew returns from SF Ruby with a lot more than conference swag! He brings a clear snapshot of where Ruby, Rails, and AI are headed right now. In this episode, he and Chris walk through the most impactful talks from SF Ruby, share highlights of engaging discussions with other developers and friends, reminisces about nostalgic tech items, and explores insightful conversations on the future of Rails, startup culture, AI's impact on programming, developer anxiety, and they share product ideas f...

In this episode of Remote Ruby, Chris and Andrew have a lively conversation with Brendan Buckingham and Ryan Frisch from the Rails Business Podcast. They discuss their experiences and journeys with Ruby on Rails, starting from their early encounters with the technology to hosting a specialized Rails podcast. Critical technical topics are covered, including managing Stripe API data integrity, upgrading Rails applications, and using modern JavaScript tools like Turbo Frames and Turbo Streams. B...

In this episode, guest Nate Berkopec joins Chris and Andrew to discuss the current state and cultural controversies surrounding Ruby Gems, Bundler, and open-source projects in general. The conversation dives into the split within the Ruby community, the complexities of maintaining key projects, and the challenges of funding and sustaining open-source work. Nate shares his experiences with Puma and his philosophy on community-driven contributions and project ownership. The episode also explore...

In this episode of Remote Ruby, Chris and Andrew catch up with Chris discussing the arrival of a new baby and the challenges of balancing work and parenting. Then, they dive into the complexities of dealing with OpenSSL 3.6 issues on their development environments, exploring various debugging attempts and ultimately finding a workaround. The conversation also touches on the ongoing drama within the Ruby community, expressing concerns about its impact and the need for unity. Additionally, they...