Since the start of operations in 1993, the twin 10 meter W. M. Keck Observatory telescopes have continued to maximize their scientific impact and to produce transformative discoveries that keep the observing community on the frontiers of astronomical research. Upgraded capabilities and new instrumentation are provided though collaborative partnerships with Caltech and UC instrument development teams. The observatory adapts and responds to the observers’ evolving needs as defined in the observatory’s strategic plan, periodically refreshed in collaboration with the science community. This paper summarizes the performance of recently commissioned infrastructure projects, technology upgrades, and new additions to the suite of instrumentation at the observatory. We will also provide a status of projects currently in the design or development phase, and since we need to keep our eye on the future, we mention projects in exploratory phases that originate from our strategic plan. Recently commissioned projects include telescope control system upgrades, OSIRIS spectrometer and imager upgrades, and deployments of the Keck Cosmic Web Imager (KCWI), the Near-Infrared Echellette Spectrometer (NIRES), and the Keck I Deployable Tertiary Mirror (KIDM3). Under development are upgrades to the NIRSPEC instrument and adaptive optics (AO) system. Major instrumentation in design phases include the Keck Cosmic Reionization Mapper and the Keck Planet Finder. Future instrumentation studies and proposals underway include a Ground Layer Adaptive Optics system, NIRC2 upgrades, the energy sensitive instrument KRAKENS, an integral field spectrograph LIGER, and a laser tomography AO upgrade. Last, we briefly discuss recovering MOSFIRE and its return to science operations.