With a voice command or a few taps on the console, the spacecraft pivots on a dime at high velocity and gently docks to an orbiting space platform. This is the image most people have of the complex software computations and integrated hardware performance necessary for a spacecraft to successfully perform an automated launch, rendezvous, and docking. Today’s reality is that while computer operations are advancing rapidly, science fiction over-simplifies and over-sells current capabilities. This paper discusses the integration of spacecraft computer automation into the operation of one of the United States’ new Commercial Crew vehicles - the Boeing CST-100 Starliner. Lessons learned by the Boeing Mission Operations team, a private-public partnership with NASA, from conceptual design through real-time operation of the first test flight will be discussed. Focus will center on how operations has learned to use the automated software to their advantage while also knowing how to adjust the automation in response to spacecraft or mission anomalies. One goal of advanced spacecraft automation is the ability to reduce both the crew workload and the ground control footprint while at the same time increasing spacecraft and mission flexibility. Historically, crewed spacecraft required a large number of operators on the ground to use a plethora of tools to compute nominal and contingency mission trajectories. Moving those sophisticated software tools to being onboard the vehicle can reduce the need for such complex ground support. Given that today’s spacecraft software is not yet as capable or as flexible in all circumstances as the computers depicted in movies, there is usually a trade-off between software automation cost and the flexibility of that software resulting in a trade-off between what is performed on the spacecraft and what is left to onboard crew or ground control. For missions that go beyond the Moon, software that autonomously controls nearly every aspect of a crewed mission will become a necessity given the long time delays between the spacecraft and Earth’s ground control teams. The lessons learned by Boeing and its Mission Operations team, through the design and implementation of Starliner’s hardware and software automation, will be able to inform future public and private spacecraft design. As the technologies and capabilities evolve, incorporating lessons learned in successful low Earth orbit commercial crew vehicle missions, spacecraft designs will continue to improve and be able to better enable safe execution of human missions to the Moon and beyond.