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 X
• Andrew Mason Bluesky
• David Hill LinkedIn
• Judoscale- Remote Ruby listener gift
• Setting up code for your repository (GitHub Docs)
• Surviving rolling deploys when Sidekiq meets a class it doesn’t know yet (Dmitry Tsepelev blog post)
• Why a Sidekiq job class you just deployed can still be “missing” (reddit)
• Ignore programmatically (Honeybadger)
• Mastodon on Spinel (intertwingly blog)
• The Odyssey
• Alex Edelman X post 

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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 rails with a highly questionable plan to corner the personalized license plate market. Hit download now!

Links

• Chris Oliver X
• Andrew Mason Bluesky
• David Hill LinkedIn
• Judoscale- Remote Ruby listener gift
• HCL-GitHub
• Thoughtbot- AI in Focus: A new Claude Skill for Rails code audits
• Madison Kanna X (chat with co-founder of OpenCode, Dax Raad)
• Josh Pigford X
• knockoff
• Taylor Otwell X post

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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 attacking solar panels. Hit download now to hear more! 

Links

• Judoscale- Remote Ruby listener gift
• Blue Apron  (Andrew’s referral code: ANDREW4838)
• GitHub Blog: Actions steps can now be run in parallel
• Codeberg
• GitLab
• GitHub apple/container
• GitHub apple/Core AI Models
• RubyConf July 14-16, 2026, Las Vegas, NV 
• Rails World 2026, September 23-23, 2026, Austin, TX

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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 anticipation surrounding GTA VI. Hit the download button now! 

Links

• Judoscale- Remote Ruby listener gift
• Obsession 
• Toy Story 5
• Porsche reveals three one-of-one 911 models on the red carpet at the World Premiere of Toy Story 5 (Porsche Newsroom US)
• Here are the Rails World 2026 speakers (Ruby on Rails)
• Typesense side-by-side feature comparison
• Bootstrap (mise)
• mise oci 
• mise membership
• Grand Theft Auto VI
• RubyConf, Las Vegas, July 14-16, 2026
• Rails World, Austin, TX, Sept 23-24, 2026

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason 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, mail delivery cancellation, and a tiny Rails PR born from production debugging. Hit download now to hear more! 

Links

• Judoscale- Remote Ruby listener gift
• Podia
• Support only: and except: on _deliver callbacks in ActionMailer #57581
• Improve documentation/testing of abort in Action Mailer ‘before_action #57489
• Mailbin- GitHub

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

[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 Australia, other conferences coming up, and reminisce about their childhood love for trains and Thomas the Tank Engine.  The episode wraps up with Chris and Andrew sharing advice and tips on writing conference proposals (CFPs) and the value of diverse speaking styles and personalities for engaging an audience. Tune in now to hear more!

Links

• ONCE/Campfire
• debug.rb
• GitHub Copilot
• RubyConf Australia-April 11-12, 2024
• RailsConf 2024-May 7-9, 2024-Detroit, MI
• Sarah Mei-“What Your Conference Proposal is Missing”
• Ruby for All Podcast-Episode 50: The Art of Conference Speaking with Kevin Murphy
• [SFM] We like to party (YouTube)
• Ultimate Skyrim (YouTube)
• RailsConf 2023-Teaching Capybara Testing- An Illustrated Adventure by Brandon Weaver (YouTube)

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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

• Judoscale- Remote Ruby listener gift
• Minnebar
• Ruby 4.0.5 Released 
• ReviseAuth
• The Ruby on Rails Podcast

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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 agents and delivery robots. Hit download now to hear more! 

Links

• Judoscale- Remote Ruby listener gift
• Dungeon Crawler Carl 
• Dungeon Crawler Carl RPG + Unstoppable
• Maciej Mensfeld X
• Aube
• Jeff Dickey X
• en.dev
• The Hacker News- RubyGems Suspends New Signups After Hundreds of Malicious Packages Are Uploaded
• One engine, many tools—Introducing Rubydex (Rails at Scale)
• Ruby 4.0.4 Released
• Frontend Masters Workshop with Chris Oliver: Getting Started with Rails

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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 integrations. Hit download now to hear more! 

Links

• Judoscale- Remote Ruby listener gift
• Getting Started with Rails with Chris Oliver (Frontend Masters Live Interactive Workshop)
• Ruby Conferences 2026

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter

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

• Judoscale- Remote Ruby listener gift
• Dungeon Crawler Carl
• Everything we announced at Sessions 2026 (Stripe Blog)
• Scaling Sidekiq at Gusto (Medium)
• Scaling-Sidekiq -GitHub
• Nate Berkopec post on LinkedIn-Running Containers

• Chris Oliver X/Twitter
• Andrew Mason X/Twitter
• Jason Charnes X/Twitter