Objects do work creating expertise. This article parses how. It works with, revisits, and develops the notion of “boundary-work” located at the core of science and technology studies by Thomas Gieryn, Susan Leigh Star, and others and adds to it the notion of “orienting work” borrowing from the work of materialist feminists such as Sarah Ahmed and Maria do Mar Pereira. Working with these concepts, it shows that cybersecurity certificates make expertise topological. They demarcate, connect, create affective attachments to, and prefigure shapeshifting boundaries of cybersecurity expertise. They orient toward a maze of routes to cybersecurity expertise, a multiplicity of shifting locations in it, and toward fences that are stretched and straddled. Departing from conventional assumptions about the role of certificates in the formation of expertise, I show that rather than close off and stabilize expertise, the work of cybersecurity certificates opens and unsettles it. The cybersecurity expertise they make is preserved in continuous deformation. I also show that rather than fragment and fracture expertise, the work of certificates stretches, bends, and twists an expertise that remains connected. The work makes expertise of a distinctly topological quality. Engaging this moving, shapeshifting terrain politically is both exceptionally challenging and fundamentally important. The shifting expert terrain is generating a steadily expanding range of cybersecurity concerns that are inscribed ever more firmly in the socio-technical infrastructures of cybersecurity with ramifications for everyday life.