In what follows, we present the outcome of an imagined dialogue with Tim Ingold on possible future directions for an anthropologically-sensitive approach to studying Information Systems (IS) and Organization Studies (OS). The aim is to try to convey some of the strangeness and freshness that we have found in his thought, with a view to stimulating IS/OS scholars to engage further with his work and ideas. The piece takes the form of an imagined Q&A session with Tim, which we have synthesized from excerpts of previously published interviews and writings.