This foundational guide is the first in a series of guides that the Department of Homeland Security (DHS) hopes will help communities achieve their connected community goals. DHS partnered with representatives from New York (NY), San Jose (CA), Memphis (TN), Chattanooga (TN), and Colorado State University to develop this "how-to" guide to help community leaders build a digital transformation strategy. Contributors include chief information officers, chief information security officers, chief privacy officers, economists, technology experts, cyber policy professionals, risk analysts, and former municipal executives, each with unique experience driving community digital transformations.