The Internet of Things (IoT) is the science of connecting multiple devices that coordinate to provide the service in question. IoT environments are complex, dynamic, rapidly changing and resource constrained. Therefore, proactively adapting devices to align with context fluctuations becomes a concern. To propose suitable configurations, it should be possible to sense information from devices, analyze the data and reconfigure them accordingly. Applied in the service of the environment, a fleet of devices can monitor environment indicators and control it in order to propose best fit solutions or prevent risks like over consumption of resources (e.g., water and energy). This paper describes our methodology in designing a framework for the monitoring and multi-instantiation of fleets of connected objects. First by identifying the particularities of the fleet, then by specifying connected object as a Dynamic Software Product Line (DSPL), capable of readjusting while running.However, the IoT system is complex, rapidly changing, highly variable, heterogeneous, prone to risks and failure, and extremely dynamic. This implies that in the face of change, the system should have the ability to adapt itself in order to continue offering the needed performance. Dynamic proactive adaptation in particular is required to provide adjustments at runtime [2]. Furthermore, and thanks to IoT devices which are growing exponentially in number and performance, it is much more conceivable to collect real time context data, and react accordingly. Additionally, a Device Management (DM) platform monitors every device in the fleet. It can inspect specific information about the services provided by the device (coffee readiness, light status, expired merchandize, speed of car, motor condition, …), it can collect information about the context of the fleet (temperature, light, location, …) and it can report on the characteristics of the devices themselves (battery life, memory, software version, etc.). In addition to that, and poster to processing the collected data, it is responsible for controlling the fleet in order to adjust its behavior.In this sense, the paper describes our process in designing a framework for the smart monitoring and reconfiguration of a fleet of connected devices. The paper starts by presenting a motivational example-a smart irrigation fleet, which will be depicted all along the development of our framework. Our process will then be elaborated. The first step identifies the requirements for the management of fleets of connected objects. The second step discusses the particularities of IoT devices and their surroundings. Three representative dimensions are conceived; the system, the context, and the environment. The third step studies the self-adaptation approaches, and selects the Dynamic Software Product Lines (DSPL) paradigm as the mechanism that fits best our set of requirements. The fourth and final step introduces an architecture skeleton; it considers the outcome of the previous stages; the three dimensions on the on...