The world is moving towards a new generation of internet, the internet of things (IoT). This technological jump is improving the way we live by creating a bridge between the physical and the virtual world. Researchers are curious about the field from different perspectives especially managing of the complexity and dynamicity of these systems. The main problem being targeted in this chapter is that IoT systems are exposed to many structural and behavioral changes due to internal and external factors. This study is about the necessity of having a mechanism that enables IoT systems to perform without breaks or shutdowns regardless of context changes. The solution consists of a contextual dynamic reconfiguration process implemented by a reflexive multilayered architecture. This process is based on the autonomic computing loop. The authors also integrated evolution styles to make reusable the reconfigurations applied on the architecture of the system. Validation of the proposed approach was made on an e-health scenario, which was simulated using Cisco Packet Tracer before performing real development.