Smart cities provide integrated management and operation of urban data emerging within a city, supplying the infrastructure for smart city services and resolving various urban challenges. Nevertheless, cities continue to grapple with substantial issues, such as contagious diseases and terrorism, that pose severe financial and human risks. These problems sporadically arise in various locales, and current smart city frameworks lack the capability to autonomously identify and address these issues. The challenge intensifies especially when trying to recognize and respond to unprecedented problems. The primary objective of this research is to predict potential urban issues and support their resolution proactively. To achieve this, our system makes use of semantic reasoning to understand the ongoing situations within the city. In this process, the 5W1H principles serve as inference rules, guiding the extraction and consolidation of context. Firstly, utilizing domain-specific annotation templates, we craft a semantic graph by amalgamating information from various sources available in the city, such as municipal public data and IoT platforms. Subsequently, the system autonomously infers and accumulates contexts of situations occurring in the city using 5W1H-based reasoning. As a result, the accumulated contexts allow for inferring potential urban problems by identifying repeated disruptions in city services at specific times or locations and establishing connections among them. The main contribution of this paper lies in proposing a comprehensive conceptual model for the suggested system and presenting actual implementation cases and applicable use cases. These contributions facilitate awareness among city administrators and citizens within a smart city regarding potential problem-prone areas or times, thereby aiding in the preemptive identification and mitigation of urban challenges.