Storage is a central part of computing. Driven by exponentially increasing content generation rate and a widening performance gap between memory and secondary storage, researchers are in the perennial quest to push for further innovation. This has resulted in novel ways to “squeeze” more capacity and performance out of current and emerging storage technology. Adding intelligence and leveraging new types of storage devices has opened the door to a whole new class of optimizations to save cost, improve performance, and reduce energy consumption. In this dissertation, we first develop, analyze, and evaluate three storage exten- sions. Our first extension tracks application access patterns and writes data in the way individual applications most commonly access it to benefit from the sequential throughput of disks. Our second extension uses a lower power flash device as a cache to save energy and turn off the disk during idle periods. Our third extension is designed to leverage the characteristics of both disks and solid state devices by placing data in the most appropriate device to improve performance and save power. In developing these systems, we learned that extending the storage stack is a complex process. Implementing new ideas incurs a prolonged and cumbersome de- velopment process and requires developers to have advanced knowledge of the entire system to ensure that extensions accomplish their goal without compromising data recoverability. Futhermore, storage administrators are often reluctant to deploy specific storage extensions without understanding how they interact with other ex- tensions and if the extension ultimately achieves the intended goal. We address these challenges by using a combination of approaches. First, we simplify the stor- age extension development process with system-level infrastructure that implements core functionality commonly needed for storage extension development. Second, we develop a formal theory to assist administrators deploy storage extensions while guaranteeing that the given high level goals are satisfied. There are, however, some cases for which our theory is inconclusive. For such scenarios we present an experi- mental methodology that allows administrators to pick an extension that performs best for a given workload. Our evaluation demostrates the benefits of both the infrastructure and the formal theory.