$ cat post/the-config-was-wrong-/-a-system-i-built-by-hand-/-i-still-have-the-diff.md

the config was wrong / a system I built by hand / I still have the diff


Title: Debugging the Reality of AI Copilots in Production


September 8, 2025. A day like any other on my engineering journey, but with a twist. Today, I faced one of those moments where the reality of running production systems with copilots and LLMs came crashing down on me.

The morning started off routine: waking up to the familiar hum of my dev environment, grabbing a coffee, and firing up Slack for team updates. But something was different today. Slack’s prices had risen by $195k per year, according to the latest news. It’s not just a cost increase; it’s a wake-up call for how our tools are shifting from being conveniences to part of the infrastructure we can’t afford to live without.

I rolled into work and joined the daily standup. The conversation quickly turned to the new AI copilot tooling that has become ubiquitous in our platform team. Our ops engineers were discussing the latest version of Claude, which now includes a feature for generating SQL queries directly from natural language prompts. It’s almost spooky how well it works, but there are still bugs—like when it tries to insert a WHERE clause with an undefined variable.

One of my colleagues was arguing that we should be more cautious about handing over critical decisions to these AI copilots. He brought up the recent F-Droid and Google’s developer registration decree story, pointing out how security concerns can arise from integrating third-party tools into our stack. I couldn’t help but nod along; he had a point.

But as I delved deeper into the day’s tasks, I found myself wrestling with an issue that required some of my old-fashioned debugging skills. We were seeing sporadic 500 errors on one of our production microservices. The logs showed some weird SQL query issues, which seemed to be related to the copilot-generated queries.

I spent the next few hours trying to figure out where the problem was. It wasn’t in the copilot’s logic; it was in how we were handling database connections and transactions within our service. We had a piece of middleware that was supposed to ensure transactional integrity, but for some reason, it was failing when the copilot’s queries were used.

After much head-scratching, I realized that the issue lay in an optimization we had applied to reduce database load. This optimization was causing a race condition with certain types of queries generated by the copilot. It was a classic case of over-optimization leading to unforeseen bugs.

I worked through a fix and pushed it live. The service stabilized, but I couldn’t shake off the feeling that we were relying too heavily on these AI copilots. They are undoubtedly powerful tools, but they come with their own set of challenges.

Later in the day, our team had a brief discussion about Wasm + containers converging. It’s exciting to think about what this could mean for us, especially as we start moving more complex logic into edge environments. But with every new technology comes another layer of complexity that needs to be managed.

As I headed home, I couldn’t help but reflect on the day’s events. The balance between leveraging powerful AI tools and maintaining robust systems is something we all need to keep in mind. While these copilots are amazing, they aren’t infallible. We still have a lot of work to do as platform engineers to ensure that our systems remain stable and secure.


That was my day in the world of 2025—full of challenges and learning opportunities. The journey continues, one bug at a time.