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When AI Agents Go Rogue
Security vulnerabilities, AI-powered coding, and a whole lot of pull requests take center stage this week on Remote Ruby! Chris, Andrew, and David kick things off with some alarming security exploits, including a critical Active Storage vulnerability and the growing risks of AI-driven attacks. They explore how Hot Cell could make Rails file uploads safer, share frustrations over security requirements for AI plugin submissions, and discuss practical ways to make AI-assisted development more manageable. Andrew reveals his new five-file rule for creating smaller, easier-to-review pull requests, while Chris considers how AI could fundamentally change software development and Rails releases. Plus, there's talk of Discord's move toward Rust, major Active Record performance improvements, and upcoming SF Ruby plans. Hit download now! [00:00:30] Chris, Andrew, and David discuss an alarming SSH vulnerability, social engineering attacks, and cryptocurrency theft.[00:06:42] They review recent Rails security fixes, including Active Storage vulnerabilities, unsafe file processing, and potential mass assignment issues.[00:09:57] Chris explains Hot Cell.[00:12:32] Chris discusses content security policies (CSP), third-party JavaScript risks, and using AI to help secure Rails applications.[00:14:56] They discuss a controversial incident involving a Railway employee's AI agent allegedly attacking another hosting provider's website.[00:18:41] Andrew and Chris explore X-Forwarded-For errors, trusted proxies, and strategies for filtering suspicious traffic.[00:23:59] Chris shares an unexpected change in Rails content negotiation that caused JSON error pages to appear instead of HTML.[00:27:06] Andrew questions why OpenAI and Claude plugin review processes require production test accounts without multifactor authentication.[00:30:23] Andrew explains his five-file rule for AI pull requests.[00:37:10] Andrew and Chris discuss smaller projects, stacked PRs, and using multiple AI coding sessions to deliver features faster.[00:41:01] They discuss reports of Discord reducing desktop memory usage by moving away from Electron.[00:43:26] The conversation switches to RubyGems, Bundler, and Active Record improvements.[00:44:40] Chris shares his excitement about delivering the closing keynote at SF Ruby.[00:47:29] The episode ends with Andrew talking about using Claude and automated workflows to resolve security warnings, update dependencies, and increase development output.Panelists:Chris OliverAndrew MasonDavid HillSponsors:HoneybadgerJudoscaleLinks:Andrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftSecurity Advisories-GitHubHot Cell-GitHubHot Cell v1.0: Securing Active Storage in the age of AI (by Mike Dalessio)SF Ruby 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/Twitter
Vulnerabilites & AI with Nate Berkopec
Nate Berkopec returns to Remote Ruby joining Chris, Andrew, and David for a deep conversation about the latest wave of Ruby security vulnerabilities, AI-powered cybersecurity, and the rapidly changing role of software engineers. Nate shares his firsthand experience investigating a serious Ruby regex vulnerability, explains why developers need to take a more proactive approach to security, and challenges traditional development practices in an AI-driven world. From autonomous coding agents and dramatically faster development workflows to rethinking unit tests and code reviews, this episode explores why the future of programming may be less about writing code and more about building systems that deliver results. Hit download now! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftNate Berkopec WebsiteNate Berkopec XRuby 4.0.9 ReleasedFinIntercomLauren (@poteto) XMatt Pocock XChris Oliver X/TwitterAndrew Mason X/TwitterJason Charnes X/Twitter
RWX Agent-native CI/CD with Dan Manges
This week on Remote Ruby, Chris, Andrew, and David welcome Dan Manges, co-founder of RWX and former CTO of Braintree, to explore a new approach to continuous integration built for the age of AI coding agents. Dan explains how RWX uses intelligent caching, graph-based execution, and isolated agent sandboxes to dramatically improve development workflows. They dive into flaky tests, automated code validation, security concerns, and why traditional CI platforms may be struggling to keep up with AI-driven development. Plus, they discuss how engineering teams can test changes before opening pull requests, reduce infrastructure costs, and rethink the way software gets built and shipped. Hit download now to hear more! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftDan Manges (X)Dan Manges WebsiteDan Manges EmailRWXRWX (X)Using AI agents with RWXCaptain-GitHubABQ-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
Jeff Dickey is Back
Jeff Dickey is back on Remote Ruby, and he's been busy! Andrew and Chris catch up with Jeff to discuss the latest improvements to mise, including precompiled Ruby builds, automatic tool updates, and dotfile management. Jeff also introduces some of his newest projects, including packslip, a new standard designed to make software distribution more secure, and jactionlint, his modernized GitHub Actions linter. The conversation explores everything from managing secrets with fnox and cleaning up massive Rust build caches to running your own CI infrastructure at home. They also dive into AI-assisted development, the future of Ruby performance, and how AI is changing the way open source software gets built and maintained.LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftJeff Dickey WebsiteJeff Dickey XEntire Remote Ruby-Episode 341: Jeff Dickey on Mise, Precompiled Rubies, and much moremise Omarchyactionlintpackslipjactionlintfnoxmr boxingtontakusage-rs aquahkHoneybadgerHoneybadger 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
Welcome to the Slop Factory
On this episode, Chris, Andrew, and David dive into the rapidly changing world of AI-assisted development, Ruby performance, and the future of building software. They kick things off with AI-powered coding workflows before exploring the Campfire benchmarking controversy and the exciting possibilities of Roundhouse, which could dramatically improve Ruby application performance. Andrew shares his experience launching a new AI agent inside Podia, including the challenges of getting its MCP integration approved by OpenAI, managing AI costs, and testing security. The conversation shifts to optimizing GitHub Actions, reducing CI expenses, and whether developers should start hosting their own runners. They also speculate about the future of all-in-one development platforms and how AI might reshape everything from writing code to deploying applications. Hit download now!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftWhat’s New in RubyGems/Bundler 4.1, Part 1: override and prune (by SHIBATA Hiroshi)Roundhouse-GitHubJP Camara XMatt Swanson XRWXBlacksmithDiggerStreet Fighter Gears of War: E-Day (game)AnyPS5-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
Rails World 2026 Recap with John Athayde
Fresh off Rails World 2026, Chris, Andrew, David, and returning guest John Athayde unpack the surprisingly emotional conversation surrounding AI, Ruby, Rails, and the future of programming. What starts as a discussion about Spinel, Roundhouse, Rust, and Rails performance quickly turns into a much bigger question: what happens to developers when writing code is no longer the main job? They dig into AI-assisted development, changing ideas around craftsmanship and creativity, the growing importance of testing and CI, and whether frameworks like Rails become more valuable in an AI-driven world. They also reflect on the mood at Rails World, autonomous cars, AI-generated design, and why the real value of conferences may increasingly be simply getting developers together in the same room. Hit download now!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftJohn Athayde WebsiteJohn Athayde XSanket Sahu X Post- GeekyAnts landing pageSpinel- Ruby AOT Compiler-GitHubRails World 2026 Talks 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
Live At Rust, Uhh, Rails World 2026
Recorded live from Rails World 2026, Andrew, Chris, David, Jason Charnes, and eventually Andy Croll, unpack the strange mood surrounding this year’s conference. Much of the conversation centers on DHH’s keynote and the increasingly agent-driven future of software development: if AI can write, debug, and even understand the code for us, what happens to the value of frameworks, developer expertise, documentation, and even Ruby itself? They also dig into Hotwire, Active Search, Herb, Active Job Continuations, security concerns around AI-generated software, and what the Ruby community might rally around if the language becomes less central to how developers identify themselves. And because it’s Rails World, there’s plenty of barbecue, conference chaos, bad jokes, and Andy Croll crashing the podcast. Hit download now!LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftJason Charnes WebsiteAndy Croll WebsiteBuzzsproutTerry Black’s BBQBurnt End BBQPlanetScaleRubyMineAppSignalRails World 2026 Talks (YouTube)HoneybadgerHoneybadger is an application health monitoring tool built by developers for developers.BuzzSproutPodcast Hosting Made Easy.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
Rails at Scale, Roundhouse Performance, and AI-Era Supply Chain Security
Andrew and Chris are back with a packed episode covering everything from Rails World anticipation and Rails 8.2 to security, Ractors, AI-assisted development, and some ambitious new Ruby tooling. They dig into RubyGems recent spam-publishing incident and Trusted Publishing, look at Shopify’s push toward Ractor-safe Rails, and explore Roundhouse, a project experimenting with compiling Rails applications into entirely different target languages. They also talk about using Claude for project planning and open source maintenance, new approaches to AI beyond traditional LLMs, the surprisingly inexpensive architecture behind Turbopuffer, PlanetScale’s new TIN search extension, and Andrew’s move from a small Sinatra deployment service to Cloudflare Workers. Hit download now! LinksChris Oliver XAndrew Mason BlueskyDavid Hill LinkedInJudoscale- Remote Ruby listener giftAutomating Ruby Gem Releases with GitHub Actions (by Andrew Mason)Marc Benioff MOGGED Sam Altman (John Smith X Post)@graphtheory X PostRactor-age Rails: A Hot-To Guide (Rails at Scale) RoundhouseIntroducing System One Models & Jev (TypeSafe AI blog post)TurbopufferBen Dicken X post (on inverted indexes)Planet Scale: Introducing TIN: full-text search for PostgresCloudflare WorkersHoneybadgerHoneybadger 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
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
Episode 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! 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
Rails 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!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
MCP 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: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
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