- 1 hour 4 minutesEpisode 367 - Ryan Castillo
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 or shouldn’t delegate work to AI. Chris also gets candid about Hatchbox’s recent pricing increase, the financial pressure behind the decision, and why talking directly with customers may be just as important as shipping the next feature. Hit download now!
Links
- Chris Oliver X
- Andrew Mason Bluesky
- David Hill LinkedIn
- Judoscale- Remote Ruby listener gift
- Ryan Castillo X
- Ryan Castillo LinkedIn
- Knowatoa
- Wafris
- Hatchbox
- How I Use Cursor by @poteto
- Skills from A Smart Bear by Jason Cohen
- Rocky Mountain Ruby-September 28-29, 2026, Boulder, Colorado
- Rails World, Sept 23-24, 2026, Austin, Texas
- Upcoming Ruby Events Calendar
Honeybadger is an application health monitoring tool built by developers for developers.
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Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.11 September 2026, 12:00 pm - 1 hour 2 minutesRails World Prep, Herb in Rails, Stacked PR Headaches and New Ruby Tooling
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 HTML email, and why tools like ArchSpec and Rubydex could become especially useful as more code is generated by LLMs. Hit download now to hear more!
Links
- Chris Oliver X
- Andrew Mason Bluesky
- David Hill LinkedIn
- Judoscale- Remote Ruby listener gift
- Rails World-Sept 23-24, 2026, Austin, TX
- Add Herb as an HTML -aware ERB implementation #58552 (GitHub pull request)
- turbopuffer
- Agents on Rails: The LLM Benchmark Project (Rails Foundation)
- Agents on Rails : The First Benchmark Report
- Tiptap
- ArchSpec
- Rubydex
Honeybadger is an application health monitoring tool built by developers for developers.
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Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.4 September 2026, 12:00 pm - 33 minutes 16 secondsMCP Implementations and Rails World Preparations
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, Action Text, Solid Cable, custom Rails generators, and appropriately enough MCPs.
Links:
Judoscale- Remote Ruby listener gift
The Ruby on Rails Podcast-Episode 548-MCP + Generators with Andy Andrea and Rachael Wright-Munn
Rails World- Sept 23-24, 2026, Austin, Texas
Sponsors:
Honeybadger
Honeybadger is an application health monitoring tool built by developers for developers.
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Make your deployments bulletproof with autoscaling that just works.28 August 2026, 1:00 pm - 54 minutes 20 secondsErnesto Tagwerker
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 giving up the experience and judgment that good software still requires. Start listening now!
Links
- Chris Oliver X
- Andrew Mason Bluesky
- David Hill LinkedIn
- Judoscale- Remote Ruby listener gift
- Ernesto Tagwerker LinkedIn
- Ernesto Tagwerker GitHub
- FastRuby.io
- OmbuLabs
- Remote Ruby-Episode 100!! Upgrading Rails with Ernesto Tagwerker
- Blastoff Rails 2026- Fewer Tests, More Confidence by Ifat Ribon (YouTube)
- Rails Upgrade Assistant Skill (OmbuLabs Claude Code Skill)
- FastRuby-Our Rails Upgrade Methodology as Claude Skills
- Mutant-GitHub
- Philly.rb Meetup
- Philly.rb X
Honeybadger is an application health monitoring tool built by developers for developers.
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Make your deployments bulletproof with autoscaling that just works.
Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.21 August 2026, 12:00 pm - 48 minutes 15 secondsShipping Podia’s New Shop, AI Code Woes, and a Major Rails libvips CVE
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 Record queries, testing philosophy, and why sometimes the fastest solution is still jumping into the code yourself. Hit download now to hear more!
Links
- Chris Oliver X
- Andrew Mason Bluesky
- David Hill LinkedIn
- Judoscale- Remote Ruby listener gift
- RSpec View specs
- Podia- Learn more about the Shop feature and how to get started
- Spider-Man: Brand New Day
- The Odyssey
- Daredevil (TV Series)
- The Bear (TV Series)
- rails–forensics–CVE–2026-66066
Honeybadger is an application health monitoring tool built by developers for developers.
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Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.14 August 2026, 12:00 pm - 1 hour 17 minutesSF Ruby 2026 with Irina and Vladimir
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-assisted development, hidden pockets of Ruby adoption, and how the community can help the next generation of companies confidently build and grow with Rails. Hit download now!
Links
- Chris Oliver X
- Andrew Mason Bluesky
- David Hill LinkedIn
- Judoscale- Remote Ruby listener gift
- Irina Nazarova LinkedIn
- Vladimir Dementyev LinkedIn
- Evil Martians
- San Francisco Ruby Startup Conference- November 10-12, 2026, San Francisco, CA
- Garry Tan X
- SF Ruby News Feed
- SF Ruby Job Board
- Using Rails – Companies using Ruby on Rails
Honeybadger
Honeybadger is an application health monitoring tool built by developers for developers.
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Make your deployments bulletproof with autoscaling that just works.
Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.7 August 2026, 12:00 pm - 41 minutes 32 secondsBig Wins For RubyConf and Grandma
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 the economics of building products. Hit download now!
Links
- Chris Oliver X
- Andrew Mason Bluesky
- David Hill LinkedIn
- Judoscale- Remote Ruby listener gift
- Brockovich AI Data Center Reporting
- Raspberry Pi
- Rails World, Austin, TX, Sept 23-24, 2026
- SF Ruby, San Franciso, CA, Nov 10-12, 2026
- MagicMirror2
Honeybadger
Honeybadger is an application health monitoring tool built by developers for developers.
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Make your deployments bulletproof with autoscaling that just works.
Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.31 July 2026, 12:00 pm - 52 minutes 8 secondsA Deep Dive into GitHub Actions
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
Honeybadger
Honeybadger is an application health monitoring tool built by developers for developers.
Judoscale
Make your deployments bulletproof with autoscaling that just works.
Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.24 July 2026, 12:00 pm - 52 minutes 46 secondsDont Steal Our Business Idea
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
Honeybadger
Honeybadger is an application health monitoring tool built by developers for developers.
Judoscale
Make your deployments bulletproof with autoscaling that just works.
Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.17 July 2026, 12:00 pm - 39 minutes 44 secondsThe Great Falcon Defense and CI Innovations
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
Honeybadger
Honeybadger is an application health monitoring tool built by developers for developers.
Judoscale
Make your deployments bulletproof with autoscaling that just works.
Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.10 July 2026, 12:00 pm - 59 minutesChris Is Back And Ready To Rant
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
3 July 2026, 12:00 pm - More Episodes? Get the App