Jane Wilkin
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Writing

On cloud engineering, collaboration, and the human side of building technology.

  • March 2026

    Eight Years Operating a Distributed Proxy

    The SRE team wasn't just operating the system -- we were continually advocating for the feedback loop between production behavior and engineering decisions.

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  • March 2026

    Failure Modes and Blast Radius

    Failure modes are rarely anticipated during system design. A single customer backend slowdown could cascade through DNS failover, thundering herd, and multi-customer outages -- all because of a health check that wasn't built to detect its own inability to serve.

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  • March 2026

    What I Believe About the Code Change Process

    What I've learned about code changes, documentation, and review over two decades, starting in an industry where the documentation trail carried real consequences.

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  • March 2026

    Don't Let People Yell at You

    Some of the most impactful mentorship I've participated in had nothing to do with technical skills. It was about navigating the moments when smart, passionate people come into conflict.

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  • March 2026

    Why I Document Everything

    I document my work obsessively, and it's not because anyone asked me to. It comes from frustration, practicality, and a desire to make things easier for whoever comes next.

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  • March 2026

    Users Act in Predictably Chaotic Ways

    Once we solved the problem of creating test environments reliably, a new set of problems appeared -- and they were all about how people actually used the system.

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  • March 2026

    From Content Analyzer to Policy Research Platform: Building Trans Discourse

    The project behind the workflow articles. How a tool for analyzing anti-trans media evolved into a policy research platform tracking legislation, organizational influence, and contested research, all built with Claude in 26 days.

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  • March 2026

    Forty Tasks, Zero Conflicts: What I Rebuilt When Concurrency Broke the Backlog

    The flat markdown backlog worked beautifully until six agents started shipping in parallel. Per-task files, tiered CI, and a merge queue turned constant merge conflicts into smooth concurrent development.

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  • February 2026

    Five Reviewers, Three Advisors, One Leader: How I Taught Claude to Plan

    When AI agents handle coordination, the bottleneck moves to planning. How I built a role-based review system that turns eight different perspectives into a prioritized backlog, and what forty-six sprints taught me about the shape of the work.

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  • February 2026

    Six Agents, One Codebase: Coordination Patterns from Human Teams

    When Claude Code handles implementation, the bottleneck moves to planning and coordination. How I built a sharable template for managing multiple AI agents, drawing on two decades of software team patterns.

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  • February 2026

    Leading the Migration Everyone Depended On

    How I built the case for migrating a legacy MySQL database to Aurora Global on a platform handling over a billion API calls a month, and why the hardest part wasn't the technical work.

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  • January 2026

    Driving DevOps Maturity: Implementing a Fully Code-Driven Build System

    How we transitioned from error-prone manual processes to a fully automated, code-driven approach using Packer, Ansible, Terraform, and Docker, and why openness, transparency, and repeatability matter more than any specific tool.

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© 2026 Jane Wilkin