This chapter advances an articulation of the contemporary knowledge worker as an infrastructural bricoleur. The practical and pragmatic intelligence of the contemporary knowledge worker, particularly those involved in project-based work, reflects an ability to build adaptable practices and routines, and to develop a set of working arrangements that is creative and event-laden. Like Ciborra’s octopi, workers augment infrastructures by drawing on certain forms of oblique, twisted, flexible, circular, polymorphic and ambiguous thinking until an accommodation can be found. These workers understand the non-linearity of work and working, and are artful in their pursuits around, through and beyond infrastructural givens. Modern knowledge work, then, when looked at through the lens of infrastructure and bricolage, is less a story of failure to understand, a limitation in training or the shortcomings of a system, but instead is more a mirror of the contemporary realities of today’s knowledge work drift as reflected in individuals’ sociotechnical practices.