Outdoor-to-indoor signal propagation poses significant challenges to millimeter-wave link budgets. To gain insight into outdoor-to-indoor millimeter-wave at 28GHz, we conducted an extensive measurement campaign consisting of over 2,200 link measurements in West Harlem, New York City, covering seven highly diverse buildings. A path loss model constructed over all measured links shows an average of 30dB excess loss over free space at distances beyond 50m. We find the type of glass to be the dominant factor in outdoor-to-indoor loss, with 20dB observed difference between grouped scenarios with low-and high-loss glass. Other factors such as the presence of scaffolding, tree foliage, or elevated subway tracks, as well as difference in floor height are also found to have a 5–10dB impact. We show that for urban buildings with high-loss glass, outdoor-to-indoor downlink capacity up to 400Mb/s is supported for 90% of indoor customer premises equipment by a base station up to 40m away. For buildings with low-loss glass, such as our case study covering multiple classrooms of a public school, downlink capacity over 2.8/1.4Gb/s is possible from a base station 57/133m away within line-of-sight. We expect these results to help inform the planning of millimeter-wave networks targeting outdoor-to-indoor deployments in dense urban environments, as well as provide insight into the development of scheduling and beam management algorithms.