Many of NASA's successful missions of robotic exploration have gone on to highly productive mission extensions, from Voyager, Magellan, Ulysses, and Galileo, to the Mars Exploration Rovers Spirit and Opportunity, a variety of Mars orbiters, Spitzer, Deep Impact / EPOXI, and Cassini. These missions delivered not only a high science return during their prime science phase, but a wealth of opportunities during their extensions at a low incremental cost to the program. The success of such mission extensions can be traced to demonstration of new and unique science achievable during the extension; reduction in cost without significant increase in risk to spacecraft health; close inclusion of the science community and approval authorities in planning; intelligent design during the development and prime operations phase; and well crafted and conveyed extension proposals. This paper discusses lessons learned collected from a variety of project leaders which can be applied by current and future missions to maximize their chances of approval and success.