We consider a sample of IT managers in SMEs in Italy and investigate what influences their evaluation of the objectives of, the obstacles to and the drivers of ICT adoption. Our results show that adoption decisions are highly path-dependent, as managers’ perceptions of the benefits of technologies significantly depend on previously adopted technologies and equipment. Firm specific characteristics, such as firm size and cost structures, also matter, though to a lesser extent. In terms of policy and managerial implications, our empirical findings suggest that in contexts where network effects matter, obstacles to adoption are eased by the development of compatible standards in the market. Furthermore, the diffusion of standards and information reduces uncertainties about innovations and might prove a successful strategy for encouraging their adoption by SMEs.