IS/business alignment has been a major concern of IT managers for many years but we seem to be little closer to a solution. This paper extends earlier research that developed a theory of alignment that clearly demonstrates that the actions of both business and IT managers are bound by organisational factors. This bounding tends to reinforce the status quo making any changes to the situation extremely problematic. The theory is used to explain the results of other alignment research and to demonstrate the intractable nature of alignment. It is argued that both business and IT managers must be aware of the effect of their current decisions on future decisions and the use of IT to gain competitive advantage.