Small, inexpensive, satellite platforms offer opportunities for pathfinder experiments, space qualification of components and systems, and enhancement of larger assets. The Optical Communication and Sensor Demonstration (OCSD) has become a three CubeSat flight test funded by NASA’s Small Spacecraft Technology Program (SSTP) under the Space Technology Mission Directorate. A 1.5U CubeSat using COTS hardware was designed, fabricated, tested, and delivered for launch. This Pathfinder CubeSat will fly by the fourth quarter of 2015. It will demonstrate proof-of-principle optical communications at a very modest threshold objective data rate of 5 Mb/s from low Earth orbit to a ground station. Two more CubeSats, with potential data rates of up to 500 Mb/s and propulsion, are under construction and will fly in January 2016. These CubeSats will demonstrate improved communications capability and the secondary OCSD goal of demonstrating proximity operations between two identical spacecraft using differential drag, a water vapor thruster, GPS measurements, and a laser rangefinder. The current launch schedule provides one to two months of Pathfinder operation before the final two flight units are delivered. We will attempt to implement lessons learned from the Pathfinder in the final flight units to demonstrate a new “Fly as you fly” paradigm enabled by the significant number of CubeSat launch opportunities available each year.