Building a database deployment pipeline with AI assistance sounds straightforward…until the AI starts treating temporary security shortcuts as permanent architecture.
In part three of his series on building an app and database almost entirely through an LLM, Grant Fritchey walks through using GitHub Copilot and VSCode to configure Redgate Flyway for PostgreSQL on Azure Flexible Server, provision a self-hosted GitHub Actions runner inside a private VNet, and wire it all together into an automated CI/CD pipeline.
The result is impressively functional — but the process surfaces a critical lesson: AI coding assistants are fast, capable, and dangerously confident

