Marty Haught joins Robby to discuss the sustainability of open-source projects, the challenges of maintaining RubyGems, and why the metaphor of technical debt may not fully capture how software ages. Instead, he suggests thinking of it as drift—the natural misalignment of software with its evolving purpose over time.

They also dig into security challenges in package management, including how Ruby Central worked with Trail of Bits to audit RubyGems. Marty also shares insights on the EU Cyber Resilience Act and how it might affect open-source maintainers worldwide. Finally, they explore how companies can support open-source sustainability through corporate sponsorships and individual contributions.

• [00:01:00] The two pillars of maintainable software: good tests and readability.
• [00:02:40] From Perl to Ruby: How readability changed Marty's approach to programming.
• [00:07:20] Is technical debt the right metaphor? Why "drift" might be a better fit.
• [00:11:00] What does it take to maintain RubyGems? Marty's role at Ruby Central.
• [00:14:00] Security in package management: How RubyGems handles vulnerabilities.
• [00:16:40] The role of external audits: Partnering with Trail of Bits for security improvements.
• [00:20:40] EU Cyber Resilience Act: How new regulations might affect open-source projects.
• [00:26:00] Funding open source: Why corporate sponsorships are becoming essential.
• [00:33:40] Advocating for technical debt work in teams: How to make a compelling case.
• [00:38:20] Processes in distributed teams: Balancing structure with flexibility.

• Technical debt is often misunderstood. The real issue may not be shortcuts taken in the past, but the way software naturally drifts from its original purpose.
• Security in package management is a growing concern. Open-source ecosystems like RubyGems require continuous investment to remain secure.
• Open source needs sustainable funding. Relying on volunteers is not a long-term solution—companies need to contribute via corporate sponsorships.
• Advocating for code improvements requires strategy. Engineers should frame technical debt discussions around business impact, not just code quality.

• Marty Haught on LinkedIn
• Marty Haught on Twitter
• Ruby Central
• RubyGems
• Auditing the Ruby Ecosystem’s Central Package Repository – Trail of Bits
• EU Cyber Resilience Act Overview
• What the EU's New Software Legislation Means for Developers (GitHub Blog)
• Ruby Central Open Source Program – Get Involved
• Corporate Sponsors Program
• Give and Take by Adam Grant

• LinkedIn
• Twitter
• BlueSky

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Subscribe to Maintainable on:

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Mike Bowers, Chief Architect at FairCom, has spent decades navigating the evolution of database technology. In this conversation, he and Robby explore the challenges of maintaining a 40+ year-old codebase, balancing legacy constraints with forward-thinking design, and the realities of technical debt.

Mike shares how FairCom transitioned from ISAM-based databases to modern JSON-driven APIs, the trade-offs between strict schemas and flexible document stores, and how software architecture plays a critical role in long-term maintainability. He also explains why human-readable JSON simplifies debugging, how documentation-driven development improves API usability, and why many software teams struggle with refactoring at the right time.

• [00:05:32] The role of software architecture in long-term maintainability
• [00:10:45] Why FairCom's legacy ISAM technology still matters today
• [00:14:20] Transitioning to a JSON-based API for modern developers
• [00:19:40] The challenges of maintaining 40+ years of C code
• [00:24:10] Technical debt: What it really means and how to manage it
• [00:28:50] The trade-offs between strict schemas and flexible NoSQL approaches
• [00:34:00] When to refactor vs. when to start over from scratch
• [00:38:15] The influence of product management thinking on software architecture
• [00:42:30] Advice for engineers considering a shift into architecture roles

• FairCom
• Mike Bowers on LinkedIn
• FairCom on Twitter/X

The Influential Product Manager by MSc Bucero

Need a smoother way to share your team's inbox? Jelly’s got you covered! 🍇✨

Jelly is perfect for small teams — because it was built by a small team. If you struggle with keeping your team’s knowledge organized and accessible, check out Jelly, a lightweight knowledge management tool designed to make finding answers easy—without all the clutter of traditional wikis. No more sticky situations or knowledge gaps—Jelly keeps everything smooth, and shareable.

Bonus for Maintainable listeners Get 20% off your first year at letsjelly.com/maintainable,

Subscribe to Maintainable on:

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Join Robby as he chats with Lorna Mitchell, open source advocate and technical writer, about the art of creating documentation that doesn’t gather dust. Lorna shares her experiences as a maintainer of the open source project RST2PDF, the value of API governance, and how documentation bridges gaps in developer experience.

• What Makes Software Maintainable: Characteristics like great documentation, automated tests, and onboarding ease.
• Documentation's Role in Long-Lived Software: Why it’s crucial for internal tools and open source projects alike.
• Open Source in Practice: Lorna’s journey with RST2PDF and adopting a tech stack she wasn’t initially fluent in.
• API Governance Simplified: Lorna explains the four levels of API readiness and how teams can work toward more usable APIs.
• Writing Documentation for Engineers: How style guides can empower contributors without overwhelming them.
• Using Tools to Improve Documentation: From linters to prose-checking tools like Veil, Lorna discusses practical tips.

• [00:01:00] What makes software well-maintained: documentation, accessibility, and automated tests.
• [00:03:10] Why documentation isn’t just for new users—Lorna’s experience with revisiting her own open source projects.
• [00:06:30] Diving into rst2pdf: Challenges in maintaining an abandoned project.
• [00:13:45] Balancing ownership and transitioning open source projects to new maintainers.
• [00:15:30] What is OpenAPI, and how does API governance impact usability?
• [00:26:10] The art of concise yet helpful documentation for different audiences.
• [00:33:00] Using examples in APIs to enhance clarity and reduce confusion.
• [00:40:00] Tools for improving writing, from prose linters to markdown syntax checkers.

• Lorna Mitchell’s Website
• rst2pdf Project
• Simon Willison’s Post on One-Person Projects
• How to Take Smart Notes
• OpenAPI Specification
• Veil Prose Linter

Follow Lorna:

• GitHub
• IndieWeb

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In this episode of Maintainable, Robby sits down with Carola Lilienthal, Software Architect and Managing Director at WPS. Together, they explore the intersection of cognitive science and software architecture, strategies for tackling technical debt, and why simplicity, modularity, and domain knowledge are crucial for maintainability.

Carola shares her approach to improving legacy systems, fostering domain-driven development, and introducing sustainable patterns into software design. She also discusses the Modularity Maturity Index (MMI), a tool her team has used to assess and improve over 300 systems.

• [00:00:43] What makes software maintainable?
• [00:01:24] The importance of clear structure, modularity, and simplicity in software.
• [00:02:38] How patterns help reduce complexity and onboard developers faster.
• [00:04:42] Addressing the challenges of systems with mixed architectural patterns.
• [00:06:20] Strategies for fostering creativity while maintaining simplicity.
• [00:07:05] How to guide teams to balance technical experimentation and maintainability.
• [00:14:03] Practical techniques for documenting architecture and decisions.
• [00:16:17] What is the Modularity Maturity Index (MMI), and how does it measure system health?
• [00:18:02] Common mistakes in managing technical debt and how to avoid them.
• [00:21:20] Why domain knowledge is essential for innovation and problem-solving.
• [00:33:03] Evolving legacy systems with domain-driven design and transformation.

• Modularity matters: Simplified, modular systems with high cohesion and loose coupling reduce cognitive load and technical debt.
• Patterns as a shared language: Establishing a pattern language within your team creates consistency and eases onboarding.
• Cognitive science in software: Architecture aligned with how our brains process complexity results in more maintainable systems.
• Domain knowledge drives innovation: Teams should focus their creativity on solving domain-specific problems, not over-complicating the architecture.
• The value of architecture documentation: Keeping clear decision records helps teams navigate legacy code and onboard new developers.

• Carola’s LinkedIn
• WPS Website

• Sustainable Software Architecture
• Domain-Driven Transformation (English version coming soon)
• Modularity Maturity Index Overview

• Reinventing Organizations by Frédéric Laloux
• Team Topologies by Matthew Skelton and Manuel Pais

Be sure to follow Carola on LinkedIn and X.

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• The importance of changeability as a core characteristic of well-maintained software.
• How GitHub has approached accessibility as a business and legal imperative.
• The evolution of GitHub’s frontend system, spanning over 2,000 pages, and the concept of "frontend vintages."
• Primer: GitHub’s design system and the paradox of its success—consistency vs. changeability.
• The disproportionate maintenance costs of frontend systems compared to backend systems.
• Using tools like Axe and keyboard-only tests to identify and resolve accessibility issues.
• The philosophical balance between creativity and usability in software design.
• Practical advice for teams starting their accessibility journey with limited resources.
• How frontend complexity affects scalability, especially in app-like experiences.
• Joel’s advocacy for adopting off-the-shelf components to reduce complexity for smaller teams.

Joel explains how changeability—the confidence to make and deploy changes—provides the foundation for high-quality software.

The Microsoft acquisition drove GitHub’s investment in accessibility, introducing SLAs, automated tools, and manual processes to track progress.

Primer fosters consistency but introduces the challenge of making changes across a vast, interconnected system.

Joel shares how browser quirks, device diversity, and other variables make frontend maintenance far more expensive than backend systems.

Joel recommends focusing on key user workflows like signing up, making payments, and completing core tasks. He emphasizes the importance of tools like Axe and keyboard-driven tests.

• [00:01:12] What Makes Software Well-Maintained? Joel shares how changeability drives quality.
• [00:03:05] GitHub’s Accessibility Journey: The role of SLAs, audits, and automation.
• [00:08:49] Primer and Design Systems: Balancing consistency with innovation.
• [00:12:54] The Hidden Costs of Frontend Complexity: Lessons learned at GitHub.
• [00:20:33] Balancing Creativity with Usability: Joel reflects on the intersection of design and functionality.
• [00:28:05] Accessibility Best Practices: Where teams should focus their initial efforts.

• Joel Hawksley’s Website
• Primer Design System
• Axe Accessibility Tools
• GitHub’s ViewComponent Framework

• How Buildings Learn by Stewart Brand

• Joel Hawksley on GitHub
• Joel Hawksley’s Website

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

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Use the code maintainable to get a 10% discount for your first year. Check them out!

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Austin Story, Senior Engineering Director at Doximity, joins Robby to explore the intricacies of building maintainable systems, fostering team accountability, and enabling faster iteration without sacrificing quality. Austin shares how his team approached migrating from a monolithic GraphQL architecture to a federated model, why simplicity matters for long-term success, and how guiding principles like YAGNI influence his decision-making.

Doximity is a leading digital platform for medical professionals, and their technology blog offers deep dives into the systems and tools that power their innovative solutions.

• [00:00:41] What is maintainable software? Austin highlights key traits, including testability, simplicity, and ease of removal.
• [00:02:09] Designing for removability: Why it's important and how it enables iterative progress.
• [00:03:05] YAGNI (You Aren’t Gonna Need It): How this principle shapes Austin's approach to feature development.
• [00:04:13] Migrating to GraphQL Federation: Benefits of breaking up a monolithic GraphQL server and the challenges faced during the transition.
• [00:05:56] GraphQL vs. REST: How GraphQL aids developer productivity while maintaining backward compatibility.
• [00:10:53] Collaboration between data and application teams: Using tools like Kafka to bridge gaps and improve workflow.
• [00:17:00] Upgrading Ruby on Rails applications: Balancing autonomy with central guidance for seamless updates.
• [00:27:55] Fostering ownership on teams: The cultural practices that empower engineers to take initiative and drive results.
• [00:34:29] Prioritizing work effectively: How Austin's team uses quarterly planning and measurable "goalposts" to align efforts with impact.
• [00:40:00] Avoiding bike-shedding: Keeping meetings and reviews focused on meaningful progress.

• Simplicity Wins: Maintainable software is easier to adapt, remove, and iterate on when it's kept simple.
• Iterate and Refine: Use principles like YAGNI to avoid over-engineering and ensure systems are built to evolve.
• Collaboration Drives Success: Bridging communication between specialized teams can unlock untapped potential.
• Focus on Outcomes: Define clear goals and track measurable results to ensure projects align with business needs.

• YAGNI (You Aren’t Gonna Need It)
• GraphQL Federation Overview
• Doximity Technology Blog
• The Mom Test by Rob Fitzpatrick
• Austin Story on LinkedIn
• Austin Story's Website

Follow Austin:

• LinkedIn
• Website

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Characteristics of Maintainable Software
Dan emphasizes the importance of internal consistency in codebases, automated tests, and proper documentation to preserve decision-making context.

• [00:05:32] Internal consistency: Why it matters.
• [00:08:09] Lessons from maintaining legacy codebases.

Working with Legacy Systems
Dan shares stories of upgrading ORM frameworks, introducing caching systems, and transitioning to bug tracking tools.

• [00:09:52] Replacing custom ORM systems with Hibernate and Ehcache.
• [00:13:10] Tackling high-risk components with automated testing.

Modern Authentication Challenges
As part of FusionAuth, Dan discusses building developer-friendly tools that balance local flexibility with SaaS convenience.

• [00:21:05] FusionAuth’s role in secure authentication.
• [00:28:13] Testing authentication flows locally and in CI pipelines.

Navigating Constraints in Teams
Advice for managing technical debt, advocating for team priorities, and communicating with stakeholders during lean times.

• [00:16:39] Communicating the impact of resource constraints.
• [00:19:27] Tracing single requests to understand complex systems.

Industry Trends and AI's Role
From managed services to the impact of AI on coding languages, Dan reflects on how the industry continues to evolve.

• [00:35:05] Managed services as accelerators for maintainability.
• [00:41:25] The potential and limits of AI in software development.

• Consistency and documentation in codebases reduce cognitive overhead for developers.
• Understand how your software fits into the business to prioritize effectively.
• AI might reshape the industry, but it won’t replace the need for thoughtful problem-solving.
• Opinionated frameworks like Ruby on Rails continue to offer exceptional developer ergonomics.

• FusionAuth Blog
• Dan's Personal Blog
• CIAM Weekly Newsletter
• Dan’s Book: Letters to a New Developer
• Zen and the Art of Motorcycle Maintenance
• The Asimov story mentioned

• Download FusionAuth: Get started with the self-hosted version today.
• Free Trial of FusionAuth: Experience the FusionAuth cloud for free!

• LinkedIn
• BlueSky

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Or search "Maintainable" wherever you stream your podcasts.

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In this episode of Maintainable, Robby speaks with Tom Johnson, Co-Founder and CEO of Multiplayer. Tom shares his perspectives on the evolving landscape of distributed systems, the challenges of maintaining legacy software, and how innovative tools are transforming the way teams collaborate.

• Characteristics of well-maintained software, from system-level documentation to effective workflows.
• The importance of debugging tools tailored for distributed systems.
• Anecdotes about managing technical debt, including cutting off a CEO’s database access.
• How auto-documentation and design branches in Multiplayer streamline team collaboration.
• Practical strategies for tackling technical debt and fostering developer morale.

• [00:01:16] Defining Well-Maintained Software: Tom explains why documentation, tests, and collaborative workflows are essential.
• [00:06:14] The Case for Locking Down Production: Lessons learned from a humorous but cautionary tale.
• [00:18:11] Debugging Distributed Systems: How Multiplayer’s tools simplify the debugging process.
• [00:25:00] Design Branches and Team Collaboration: Enhancing communication through shared documentation.
• [00:31:39] Prioritizing Technical Debt: Identifying customer and developer pain points.

• Multiplayer
• Tom Johnson on LinkedIn
• Tom Johnson on Twitter
• Book Recommendation: Making Comics by Scott McCloud

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

• Apple Podcasts
• Spotify

Or search "Maintainable" wherever you stream your podcasts.

Keep up to date with the Maintainable Podcast by joining the newsletter.

In this episode of Maintainable, Robby speaks with Gulcin Yildirim Jelinek, a Staff Database Engineer at Xata. Joining from Prague, Czech Republic, Gulcin discusses her experiences working with legacy databases, the evolution of Postgres, and her passion for building accessible tech communities.

Gulcin shares practical insights into modern database management, including the rise of automation tools like YAML and Pgroll, as well as how extensions like pgvector are unlocking new possibilities for Postgres users. Her work with the Prague PostgreSQL Meetup and Diva Conference highlights her dedication to fostering inclusive and welcoming tech communities.

• [00:05:32] What Makes Databases Maintainable? Gulcin reflects on documentation, onboarding, and usability.
• [00:15:10] From Legacy to Modern: Challenges with legacy systems in hospitals and banks and the transition to Postgres.
• [00:22:18] Pgvector and Vector Search: Introducing Postgres extensions to enable vector-based queries.
• [00:28:12] Scaling Automation with YAML: How YAML transformed database management and DevOps workflows.
• [00:33:00] Fostering Community and Accessibility: Gulcin’s work with Postgres Europe and Diva Conference.
• [00:36:15] Mythology with a Twist: Book recommendations featuring Circe and Elektra.

• Documentation Matters: A well-documented system ensures effective onboarding for both developers and end-users.
• Automation is Key: Tools like YAML and Pgroll streamline database operations, minimizing downtime and manual intervention.
• Inclusivity in Tech: Conferences and communities should prioritize accessibility, from catering to translation services.
• Vector Databases in Postgres: Pgvector is making Postgres a viable option for AI-driven workloads, eliminating the need for separate systems.

• Xata Blog
• Pgroll
• Prague PostgreSQL Meetup
• Diva: Dive into AI Conference
• Kadin Yazilimci (Women Developers of Turkey)
• Circe by Madeline Miller
• Elektra by Jennifer Saint

• LinkedIn
• Prague PostgreSQL Meetup
• Diva Conference

• Circe
• Elektra

• Kadin Yazilimci (Women Developers of Turkey)
• Diva: Dive into AI Conference
• Prague PostgreSQL Meetup
• On X
• Xata Blog
• Pgroll

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Or search "Maintainable" wherever you stream your podcasts.

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Robby sits down with Justine Gehring, an AI Research Engineer at Moderne, to explore how AI tools are transforming code maintenance and scalability. They dive into the unique ways AI can support refactoring for massive and legacy codebases, from retrieval-augmented generation (RAG) to lossless semantic trees, and discuss how developers can benefit from AI-assisted planning and refactoring.

Justine shares her background transitioning from academia to industry and reflects on the essential role of reproducibility in AI, why maintainable code is often overlooked in research, and the challenges of balancing innovation with real-world reliability in software projects.

• What Makes Software Maintainable: Justine’s take on good documentation, reusable code, and ensuring new team members can quickly navigate a codebase. [00:00:42]
• Academia vs. Industry in Code Maintainability: Why reproducibility and code maintenance often diverge in research settings, and how industry standards address this gap. [00:01:14]
• From Academia to AI Engineering: Justine shares her journey and how her background in machine learning led to a career in AI-focused software maintenance. [00:04:48]
• Scaling Refactoring with OpenRewrite: An introduction to OpenRewrite, the open-source tool that facilitates large-scale code transformations, developed by Moderne. [00:12:15]
• Lossless Semantic Trees: The benefits of LSTs for detailed code analysis, retaining essential syntax and type information critical for reliable AI refactoring. [00:20:24]
• Retrieval-Augmented Generation (RAG): Justine explains RAG’s significance in allowing AI models to provide context-specific responses without heavy re-training. [00:26:00]
• Trust and Validation in AI-Generated Code: The importance of robust test cases and human oversight when leveraging AI-generated code to avoid cascading errors. [00:31:36]
• AI as a Planning Tool for Refactoring Projects: Justine’s insights on using AI as a collaborative coding assistant, offering developers suggestions for planning refactoring and maintenance tasks. [00:35:24]
• Real-World Example of Scaling Refactoring: Justine recounts a case study where Moderne used OpenRewrite to facilitate large-scale code migration involving multiple frameworks. [00:42:00]
• Advocating for AI Tools in Code Maintenance: Tips for developers interested in introducing AI tools and approaches within their teams or organizations. [00:42:31]

• AI Supports Reproducibility and Reliability: Ensuring reproducibility in AI-driven tools can enhance both credibility and usability for complex codebases.
• Prioritize Planning Before Refactoring: Understanding code dependencies and structure is key to successful refactoring; AI tools like OpenRewrite can automate targeted changes.
• Human Expertise Remains Essential: AI can be an effective coding assistant, but human oversight is necessary to ensure accuracy and quality.
• Experiment and Scale: Start with small, impactful AI-assisted refactoring recipes and scale up once the process is reliable, saving significant development hours over time.

• Moderne
• Justine Gehring’s LinkedIn
• OpenRewrite Documentation
• Getting to Yes by Roger Fisher and William Ury

Turn hours of debugging into just minutes! AppSignal is a performance monitoring and error-tracking tool designed for Ruby, Elixir, Python, Node.js, Javascript, and other frameworks.

It offers six powerful features with one simple interface, providing developers with real-time insights into the performance and health of web applications.

Keep your coding cool and error-free, one line at a time! 

Use the code maintainable to get a 10% discount for your first year. Check them out!

Subscribe to Maintainable on:

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Or search "Maintainable" wherever you stream your podcasts.

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