LuaRocks is a package manager for the Lua programming language. Its codebase became more and more complex as it grew, making it difficult to understand, improve on, and maintain. Teal is a statically typed dialect of Lua. The goal of introducing type annotations to the LuaRocks codebase was to help mitigate these maintenance problems, but implementing those was not as straightforward as I had imagined. In this talk, we'll discuss both the challenges and the outcomes of this transition, which led to improvements to both LuaRocks and Teal.