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String theory has sparked much progress in thinking about spacetime in the past twenty years, involving ideas like duality, D-branes, black hole entropy, the holographic AdS/CFT correspondence, and the Landscape. Two interrelated themes will be our focus: aspects of holography and microscopic string models of black hole physics. Topics will include the firewall debate about the black hole information problem and candidate resolutions, and developments in holography involving entanglement entropy, bulk locality, and higher-spin. Recent advances on both fronts have emphasized linkages between quantum entanglement and spacetime geometry, and produced better questions about the validity of GR as an effective field theory. Many big questions in the field remain open, such as the nature of time and how quantum mechanics itself might emerge.