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In classic software engineering, a successful software architecture arises from functional and non-functional requirements analysis, modeling, design elaboration and implementation phases, incorporating key trade-offs and constraints. This paper proposes an alternative approach, informed by deep insights gained from understanding successfully deployed architectural styles in two key domains: highly scalable, resilient Web applications; and robust presence and messaging systems. We propose that the challenges and complexities within the healthcare domain can be successfully addressed with this approach. Specifically, the REST architectural style with its focus on resource oriented architecture, and the Jabber protocol set and its associated messaging and presence infrastructure. These two approaches have been successfully implemented on a global scale, have been bound to legacy information systems, and have demonstrated an ability to evolve to match the most complex organizations. The approaches are complimentary, but not without contradictions. This paper discusses these contradictions and lays out a set of challenges that, if successfully addressed, can yield a flexible, powerful and resilient architecture within a highly challenging domain.