This article provides a behaviour analysis of moment resisting joints with curved endplates. This is a new type of connection that can be used for joining steel beams to the circular hollow section (CHS) columns by means of bolts. Some researchers apply the Eurocode model without considering the differences in calculation schemes and assumptions, such as by using the general model of an equivalent T-stub in tension. Consequently, many of the existing behaviour studies are somewhat misleading, thus there is a need for further research. Apart from the absence of analytical methods that are devoted to predicting the initial stiffness and strength of the curved T-stub, other technical difficulties were encountered, such as gaps between the endplate and the column, as well as the initial pre-loading force of the bolts. In the previous studies, endplates were manufactured by rolling flat plates to the precise curvature which resulted in firm contact. In contrast, in this study, endplates were manufactured from a standard CHS tube, which led to significant initial gaps. Meanwhile, in terms of preloading force, it was found that it affected the moment resistance of the joint. This paper discusses problems associated with ongoing researches and presents experimental tests of the two connections. The obtained results were further used in the parametric finite element analysis (FEA) to determine the effect of the gaps and preloading force of the bolts on the moment resistance and initial rotational stiffness of the joint. The results indicate that the behaviour of curved plated connections is exceedingly complex and that the preloading force is the key factor, therefore, it should be controlled.