The integrity of bolted joints is still a challenging problem owing to the gross or localized slip at the interfacial surfaces of the joints when subjected to external disturbances such as vibrations. This slip escalates the interfacial movement and, thus, leads to a decrease in preload levels, that is, looseness of the bolted assemblies. In the last decade, modal analysis, wave propagation, and percussion methods were traditionally used to detect looseness in bolted connections. With an increase in computational power, machine learning algorithms such as neural networks, random forests, decision trees, and support vector machines complemented the traditional methods in accurate looseness estimation. Subsequently, this integration paved the path for real-time health monitoring of bolted joints. This paper summarizes recent investigations on looseness detection in bolted assemblies based on traditional methods and machine learning algorithms. The working principle, advantages, challenges, and applications of the aforementioned methods are also detailed in this paper. Apart from these investigations, the latest studies on the Internet of Things-based health monitoring of structures are also reviewed to explore their adaptability in remote monitoring of bolted connections for damage detection in the future. © The Author(s) 2023.