Firms began outsourcing information system functions soon after the inception of electronic computing. Extant research has concentrated on large organizations and large-valued outsourcing contracts from a variety of different industries. Smaller-sized firms are inherently different from their large counterparts. These differences between small and large firms could lead to different information technology/information system (IT/IS) items being outsourced and different outsourcing agreements governing these arrangements. This research explores and examines the outsourcing practices of very small through to medium-sized manufacturing organizations. The in-depth case studies not only explored the extent to which different firms engaged in outsourcing but also the nuances of their outsourcing arrangements. The results reveal that all six firms tended to outsource the same sorts of functions. Some definite differences existed, however, in the strategies adopted in relation to the functions they outsourced. These differences arose for a variety of reasons, including size, locality, and holding company influences. The very small and small manufacturing firms tended to make outsourcing purchases on an ad hoc basis with little reliance on legal advice. In contrast, the medium-sized firms often used a more planned initiative and sought legal advice more often. Interestingly, not one of the six firms outsourced any of their transaction processing. These findings now give very small, small-, and medium-sized manufacturing firms the opportunity to compare their practices against other firms of similar size.