Engineering leader building cloud-native automation for regulated healthcare environments.https://kevin-flessa.com/en-ushttps://kevin-flessa.com/writing/an-ai-agent-that-can-open-prs-but-never-merge-them/https://kevin-flessa.com/writing/an-ai-agent-that-can-open-prs-but-never-merge-them/I built an unattended maintenance agent that turns Sentry errors, alarms, and dependency alerts into tested pull requests. The interesting part was deciding what it's not allowed to do.Mon, 05 Oct 2026 00:00:00 GMTAIAWSMaintenancehttps://kevin-flessa.com/writing/every-decision-before-the-first-line-of-code/https://kevin-flessa.com/writing/every-decision-before-the-first-line-of-code/I built a pipeline that takes a client from discovery call to working bot with one engineer driving. The first build went from 7 weeks to 2 days. Most of the work was refusing to let it guess.Mon, 05 Oct 2026 00:00:00 GMTAIProcessSpecshttps://kevin-flessa.com/writing/what-five-years-of-neglect-does-to-a-side-project/https://kevin-flessa.com/writing/what-five-years-of-neglect-does-to-a-side-project/My personal site sat untouched from 2021 to 2026. The code didn't rot gently — it stopped building entirely, and the reasons are worth writing down.Thu, 27 Aug 2026 00:00:00 GMTToolingFrontendMaintenance