Three Rubyists having conversations and interviewing others about Ruby and web development.
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Ernesto 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! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftErnesto Tagwerker LinkedInErnesto Tagwerker GitHubFastRuby.ioOmbuLabsRemote Ruby-Episode 100!! Upgrading Rails with Ernesto TagwerkerBlastoff 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 SkillsMutant-GitHubPhilly.rb MeetupPhilly.rb XHoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Shipping 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! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftRSpec View specsPodia- Learn more about the Shop feature and how to get startedSpider-Man: Brand New DayThe OdysseyDaredevil (TV Series)The Bear (TV Series)rails–forensics–CVE–2026-66066HoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
SF 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!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftIrina Nazarova LinkedInVladimir Dementyev LinkedInEvil MartiansSan Francisco Ruby Startup Conference- November 10-12, 2026, San Francisco, CAGarry Tan XSF Ruby News FeedSF Ruby Job BoardUsing Rails – Companies using Ruby on RailsHoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Big 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!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftBrockovich AI Data Center ReportingRaspberry PiRails World, Austin, TX, Sept 23-24, 2026SF Ruby, San Franciso, CA, Nov 10-12, 2026MagicMirror2HoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
A 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!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftSetting 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 OdysseyAlex Edelman X post HoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Dont 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!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftHCL-GitHubThoughtbot- AI in Focus: A new Claude Skill for Rails code auditsMadison Kanna X (chat with co-founder of OpenCode, Dax Raad)Josh Pigford XknockoffTaylor Otwell X postHoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
The 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! LinksJudoscale- Remote Ruby listener giftBlue Apron (Andrew’s referral code: ANDREW4838)GitHub Blog: Actions steps can now be run in parallelCodebergGitLabGitHub apple/containerGitHub apple/Core AI ModelsRubyConf July 14-16, 2026, Las Vegas, NV Rails World 2026, September 23-23, 2026, Austin, TXHoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Chris 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! LinksJudoscale- Remote Ruby listener giftObsession Toy Story 5Porsche 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 comparisonBootstrap (mise)mise oci mise membershipGrand Theft Auto VIRubyConf, Las Vegas, July 14-16, 2026Rails World, Austin, TX, Sept 23-24, 2026Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Blastoff Rails Recap and Ruby Central Revamp
Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Navigating Subscription Overhauls and Payments
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! LinksJudoscale- Remote Ruby listener giftPodiaSupport only: and except: on _deliver callbacks in ActionMailer #57581Improve documentation/testing of abort in Action Mailer ‘before_action #57489Mailbin- GitHubHoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
[The lost episode 259] All Right, Rant Time - Debugging
[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!LinksONCE/Campfiredebug.rbGitHub CopilotRubyConf Australia-April 11-12, 2024RailsConf 2024-May 7-9, 2024-Detroit, MISarah 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/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Revise Auth and Podcasting Plans
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! LinksJudoscale- Remote Ruby listener giftMinnebarRuby 4.0.5 Released ReviseAuthThe Ruby on Rails PodcastChris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Rails World Tickets, New JavaScript Package Managers, and Security Worries
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! LinksJudoscale- Remote Ruby listener giftDungeon Crawler Carl Dungeon Crawler Carl RPG + UnstoppableMaciej Mensfeld XAubeJeff Dickey Xen.devThe Hacker News- RubyGems Suspends New Signups After Hundreds of Malicious Packages Are UploadedOne engine, many tools—Introducing Rubydex (Rails at Scale)Ruby 4.0.4 ReleasedFrontend Masters Workshop with Chris Oliver: Getting Started with RailsHoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Blue Ridge Ruby Insights & Experiences
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! LinksJudoscale- Remote Ruby listener giftGetting Started with Rails with Chris Oliver (Frontend Masters Live Interactive Workshop)Ruby Conferences 2026HoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake 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.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
Stripe Changes, File Upload Quirks, Scaling Sidekiq
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!LinksJudoscale- Remote Ruby listener giftDungeon Crawler CarlEverything we announced at Sessions 2026 (Stripe Blog)Scaling Sidekiq at Gusto (Medium)Scaling-Sidekiq -GitHubNate Berkopec post on LinkedIn-Running ContainersChris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter