Recent attempts at a collective understanding of how to develop an e-Health strategy have addressed the individual organisation, collection of organisations, and national levels. At the national level the World Health Organisation's National eHealth Strategy Toolkit serves as an exemplar that consolidates knowledge in this area, guides practical implementations, and identifies areas for future research. A key implication of this toolkit is the considerable number of organisational changes required to successfully apply their ideas in practice. This study looks critically at the confluence of change management and e-Health strategy using metaphors that underpin established models of change management. Several of Morgan's organisational metaphors are presented (highlighting varied beliefs and assumptions regarding how change is enacted, who is responsible for the change, and guiding principles for that change), and used to provide a framework. Attention is then directed to several prominent models of change management that exemplify one or more of these metaphors, and these theoretical insights are applied to evaluate the World Health Organisation's National eHealth Strategy Toolkit. The paper presents areas for consideration when using the WHO/ITU toolkit, and suggestions on how to improve its use in practice. The goal is to seek insight regarding the optimal sequence of steps needed to ensure successful implementation and integration of e-health into health systems using change management models. No single model, toolkit, or guideline will offer all the needed answers, but clarity around the underlying metaphors informing the change management models being used provides valuable insight so potentially challenging areas can be avoided or mitigated.