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Adaptivity is a capability that enables a system to choose amongst various alternatives to satisfy or maintain the satisfaction of certain requirements. The criteria of requirements satisfaction could be pragmatic and context-dependent. Contextual Goal Models (CGM) capture the power of context on banning or allowing certain alternatives to reach requirements (goals) and also deciding the quality of those alternatives with regards to certain quality measures (softgoals). It is used to depict facets of the decision making strategy and rationale of an adaptive system at the preliminary level of requirements. In this thesis we argue the case for pragmatic requirements and extend the CGM with additional constructs to capture them and allow their analysis. We also develop an auto- mated analysis which aids the planning and scheduling of tasks execution to meet pragmatic goals. Moreover, we evaluate our modelling and analysis regarding correctness and performance. Such an evaluation showed the applicability of the approach and its usefulness in aiding sensible decisions. It has also shown its capability to do so in a time short enough to suit run-time adaptation decision making.