Often on red teams, there is no obvious path to compromising the environment. Reconnaissance efforts, both external and internal, may yield only crumbs of information. Though tiny and often in obscure locations, these bits of information can serve as a trail of breadcrumbs to full-scale compromise. Specific keys in the Windows Registry and unusual sources of open-source intelligence gathering can provide valuable information about a network mapping that most companies don't know exist. We walk you step-by-step through what some of these crumbs are, how to find them, and how we have used tiny bits of information to escalate our privileges to full-scale enterprise compromise.