We begin with some words of caution. Note that the classic examples of human serendipity tend to focus on ground-breaking discoveries. In computational creativity, we have learned that we must not aim to build systems which perform domain-changing acts of creativity before we can build systems which can perform everyday, mundane creativity (distinguished as “big C” and “little c” creativity.) Similarly, we should be prepared to model “little s” serendipity before we are able to model “big S” serendipity. Furthermore, attempts to introduce serendipity into computer systems may initially diminish artefact value. A system which allowed itself to be derailed from a task at hand might not achieve as much as one which maintains focus. A system that uses a random search or that has its behaviour determined by environmental conditions may be deemed less intelligent than one which follows detailed, explicit, pre-programming. To such arguments, we would respond that serendipity is not “mere chance” – the axes of sagacity (skills) and useful results (recognised as such at least by the discoverer) are equally important.