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!

Links

• Chris Oliver X
• Andrew Mason Bluesky
• David Hill LinkedIn
• Judoscale- Remote Ruby listener gift
• Introducing Neki (PlanetScale blog post)
• The lifecycle of a sharded Postgres query (blog post)
• PlanetScale Blog
• Rails is built for AI.
• Agents on Rails: Stage 2. Can a model ship a feature? (Posted by Svyatoslav Kryukov, Artur Petrov, Alexander Baygeldin)
• Surfguard-GitHub
• Omachee
• Meat Proxy

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

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

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

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

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