There is some evidence of the unabated proliferation of employee-autonomous, informal in an enterprise sense, collaborative information technologies (CITs) to perform collaborative activities despite huge investments in CIT enterprise systems. This article will introduce the metaphorical construct of “shadow CIT” (similar to “shadow IT” – Raden, 2005; Schaffner, 2007) to describe the strategic choice to use autonomous CITs instead of formal enterprise CITs. “Shadow IT” has been defined by Raden (2005) as a set of IT tools used “for performing IT functions but not part of the mainstream IT organization” (p.1). Similarly, “shadow CIT” solutions are employee-autonomous: they are not implemented as part of the organisational IT infrastructure, neither have they received any targeted organisational investment. Several research questions are explored in this paper. The existence of “shadow IT” has been argued to imply a failure on the part of enterprise IT to provide all of the services to meet their users‟ needs. Does the existence of “shadow CIT” imply a failure of enterprise CITs of a similar kind? If shadow CITs are found to be [capable of] filling gaps within enterprise CITs, what kind of gaps are these? Often, without being able to articulate why, users appear to shun solutions and good architecture within enterprise CITs in favour of the ability to get their work done through autonomous “shadow” solutions. What kind of motivation may be driving such decisions?