In this talk, I will explore the not-so-fun parts of using EndpointSecurity, especially when it comes to deploying it as an end product. This is a fairly counter-intuitive process, more so when you build things outside of XCode and Apple's tool. \n\n In particular we will take a look at osquery, an open source, cross platform endpoint visibility agent, written in C++ and using CMake and CPack as the build system. We will explore how to tie all the moving parts -- from entitlements and provisioning profiles, to repackaging a CLI as an app bundle, to Full Disk Access permissions and TCC gotchas. Finally we will tie everything together with automating packaging and signing in the CI.