This dissertation expands current theoretical and practical knowledge of variability in the technological strategies practiced by past forager societies. Specifically, it examines the interplay between raw material innate and working properties, and tool design as they relate to skeletal media and technologies. Data were synthesized from existing biomedical literature on the structure and mechanical properties of technologically-relevant osseous media, including bird and cetacean bone, and antler. Original laboratory tests were then conducted to determine the mechanical properties of Young's modulus (intrinsic stiffness), intrinsic strength, and fracture resistance of the compact tissue of reindeer antler, cervid long bones, and the limb bones of the California sea lion. Cervid compact limb tissue is stiff, strong, and brittle, while reindeer antler is flexible and highly fracture-resistant (tough). Air-drying hardens all skeletal tissues, and greatly increases investment times for creating tool blanks of both antler and cervid limb bone. Water -soaking can soften dry antler, but may have little effect on the workability of previously-dried land mammal limb bone. Finally, data on the mechanical and working properties of osseous tissues were applied to an analysis of the raw material selection and tool design strategies practiced by protohistoric Alutiiq foragers of Alaska's Kodiak region. Drawing on a sample of over 300 osseous tools and tool blanks, the engineering designs of five tool types were investigated: unbarbed arrows, barbed sea mammal harpoons, fishing harpoon tips, woodworking wedges, and awls. By employing multiple analytical scales, the study points to multiple design pathways toward a generalized goal of maximizing tool longevity, or circulation time. Tool fracture potential can be reduced through raw material selection and stress-reducing structural design. Alutiiq designs for longevity include nested fish harpoon valves, and the off-set line holes on unilaterally barbed harpoons. Also, both tool types were created most frequently from tough but non-local antler. Tool recycling and conservation to avoid drying and fracture can likewise increase tool use-lives. For osseous tools, maximizing longevity might offset high initial tool production investments. The results are applicable to processes of technology transfer in many protohistoric contexts and the Upper Paleolithic of Eurasia.