Navigating the Labyrinth of Webhooks and APIs

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 architectural decisions the next. They also explore how AI is changing Chris’s work on Jumpstart and Hatchbox, improving Rails actionable errors, tackling years-old Android bugs, and potentially reshaping how open source projects are maintained. Press download now! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftIntroducing Neki (PlanetScale blog post)The lifecycle of a sharded Postgres query (blog post)PlanetScale BlogRails is built for AI. Agents on Rails: Stage 2. Can a model ship a feature? (Posted by Svyatoslav Kryukov, Artur Petrov, Alexander Baygeldin)Surfguard-GitHubOmacheeMeat ProxyHoneybadgerHoneybadger 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

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! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftRyan Castillo XRyan Castillo LinkedInKnowatoaWafrisHatchboxHow I Use Cursor by @potetoSkills from A Smart Bear by Jason CohenRocky Mountain Ruby-September 28-29, 2026, Boulder, ColoradoRails World, Sept 23-24, 2026, Austin, TexasUpcoming Ruby Events CalendarHoneybadgerHoneybadger 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

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!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftRails World-Sept 23-24, 2026, Austin, TXAdd Herb as an HTML -aware ERB implementation #58552 (GitHub pull request)turbopufferAgents on Rails: The LLM Benchmark Project (Rails Foundation)Agents on Rails : The First Benchmark ReportTiptapArchSpecRubydexHoneybadgerHoneybadger 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

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:Chris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftThe Ruby on Rails Podcast-Episode 548-MCP + Generators with Andy Andrea and Rachael Wright-MunnMCP serverMCP Ruby SDK-GitHubDoorkeeper-GitHubRails World- Sept 23-24, 2026, Austin, TexasRails World Talks Herb-GitHubReActionViewSolid Cable-GitHubSponsors:HoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.JudoscaleMake your deployments bulletproof with autoscaling that just works.Chris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter

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

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

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

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

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

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