Performance is a function of the alignment between information systems (IS) strategy and other business domains, including business strategy and organization structure. However, research has focused on the outcomes of that process, rather than the processes by which that alignment is developed. Using multiple case data, this paper investigates alignment in SMEs, explaining why different SMEs follow different paths to alignment. Four paths are identified, with the path chosen contingent on an SME’s market position. The four paths vary from simple, when the focus of the IS investment is on improving control, to complex, when the intent is to reposition the SME. The implications of these findings for management and research are explored.