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The DNN CMS is a complex ecosystem with many solutions to the same problem. Often, when given a hammer, everything looks like a nail. During the initial planning stages of a small DNN project, it may make sense to create a few custom modules to solve specific business needs. Before you know it, your "small" project now contains over 150 custom DNN modules and your team is starting to use the term "technical debt" regularly. We will explore tools and strategies to know when it makes sense to create a custom DNN module, buy an existing module, or code straight ASP.net Webforms or MVC.