Education and public engagement (EPE) is an essential part of astronomy's mission. New technologies, remote observing and robotic facilities are opening new possibilities for EPE. A number of projects (e.g., Telescopes In Education, MicroObservatory, Goldstone Apple Valley Radio Telescope and UNC's Skynet) have developed new infrastructure, a number of observatories (e.g., University of Arizona's "full-engagement initiative" towards its astronomy majors, Vatican Observatory's collaboration with high-schools) have dedicated their resources to practical instruction and EPE. Some of the facilities are purpose built, others are legacy telescopes upgraded for remote or automated observing. Networking among institutions is most beneficial for EPE, and its implementation ranges from informal agreements between colleagues to advanced software packages with web interfaces. The deliverables range from reduced data to time and hands-on instruction while operating a telescope. EPE represents a set of tasks and challenges which is distinct from research applications of the new astronomical facilities and operation modes. In this paper we examine the experience with several EPE projects, and some lessons and challenges for observatory operation.