In this presentation, we will first explore a set of commonly used technologies that may not be closely examined as part of traditional information security programs. However, they likely introduce critical risks via open apertures allowing for unauthenticated inputs by anonymous users. In this presentation, I will show you examples of how to identify assets and uncover vulnerabilities using new perspectives in this increasingly-connected world. Heavily based upon lessons learned from a 20+ year cyber career in the public sector, this presentation will provide new strategies through exciting examples that will shape how you interpret additional technologies around you and design security controls to uplift your defenses.