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Ubiquitous smart space consists of various ubiquitous objects (devices and applications) and their collaborations that provide convenient and intelligent services for users. Many studies have focused on developing convenient ubiquitous systems and their applications. However, to provide smooth and satisfactory services to users, a ubiquitous system must be aware of the real-time context of its ubiquitous objects and their collaborations during execution. Therefore, monitoring and analyzing must be provided, not only for the status of the functions and performance of individual ubiquitous objects, but also for their collaborative status. This paper discusses the challenges of monitoring systems for ubiquitous smart space, and proposes seven prerequisites for a monitoring system that examines and diagnoses ubiquitous smart space. We also developed a monitoring system for a ubiquitous smart space scenario, to verify our proposal.