Cloud-based software applications are designed to change often and rapidly during operations to provide constant quality of service. As a result the boundary between development and operations is becoming increasingly blurred. DevOps provides a set of practices for the integrated consideration of developing and operating software. Software architecture is a central artifact in DevOps practices. Existing architectural models used in the development phase differ from those used in the operation phase in terms of purpose, abstraction, and content. In this chapter, we present the iObserve approach to address these differences and allow for phase-spanning usage of architectural models.