Outsourcing is a co-operative activity undertaken to improve inter-firm transactions and is ‘a decision taken by an organisation to contract-out or sell the organisation’s IT assets, people and/or activities’ (Willcocks and Kern, 1998: 29) to external vendors, who then manage the services for an agreed fee (Barthelemy, 2003, Dibbern et al., 2004, Lacity and Willcocks, 1998). It has been argued that the broad aim for organisations outsourcing internal functions is to achieve benefits in cost, flexibility and access to resources. However, actual outcomes have been mixed with some outsourcing contracts achieving poor results with a gap between expectations and actual service performance emerging (Deloittes, 2008, Wu et al., 2013). Outsourcing is a prevalent practice and over 80% of organizations will outsource at least one service (Corbett, 2004). However, despite this widespread adoption there are performance issues, dissatisfaction and an apparent dichotomy as to why outsourcing is so prevalent, yet lacks empirical justification, and remains a largely unexplored puzzle (Jiang et al., 2006, Rouse, 2007). In this regard, outsourcing as a process, shares similar sub-optimal outcomes with other large scale changes, inter alias: Business Process Engineering (Holland and Kumar, 1995), Merger and Acquisitions (Cartwright and Cooper, 1993), the chronic problems of ERP implementations (Scarbrough et al., 2008) and even major failings in large scale project implementations (Bronte-Stewart, 2009). A recent survey of outsourcing illustrated that 65% of buyers renegotiated their contract, 30% cancelled and switched suppliers and 5% back-sourced the service in-house (Cullen et al., 2014: 51). These failings do not appear to derive from poor decision making per se but from internal factors, including poor professionalism and communication (Deloittes, 2008), lack of performance management systems and processes (McIvor et al., 2009), or possibly an attachment to implementation practices that ‘lack any scientific justification’ (Dietz, 2011: 2). Cullen et al. (2005) suggested that anecdotal stories of failure may be a consequence of too high a level of analysis, and failure to consider the configuration of the outsourcing relationship. However, when proposing the configuration or governance as key factors researchers and practitioners often remain firmly focused on instrumental and technical matters and check lists (see Oshri et al., 2009, Willcocks et al., 2006). In addition, although this focus on configuration is a useful recipe, close collaborative relationships are much more important preconditions for success, and good communication and coordination underpin successful outcomes (Vanpoucke and Veereke, 2010, Whitley and Willcocks, 2011).