Abstract: Despite the valuable information contained in software chat messages, disentangling them into distinct conversations is an essential prerequisite for any in-depth analyses that utilize this information. To provide a better understanding of the current state-of-the-art, we evaluate five popular dialog disentanglement approaches on software-related chat. We find that existing approaches do not perform well on disentangling software-related dialogs that discuss technical and complex topics. Further investigation on how well the existing disentanglement measures reflect human satisfaction shows that existing measures cannot correctly indicate human satisfaction on disentanglement results. Therefore, in this paper, we introduce and evaluate a novel measure, named DLD. Using results of human satisfaction, we further summarize four most frequently appeared bad disentanglement cases on software-related chat to insight future improvements. These cases include (i) Ignoring Interaction Patterns, (ii) Ignoring Contextual Information, (iii) Mixing up Topics, and (iv) Ignoring User Relationships. We believe that our findings provide valuable insights on the effectiveness of existing dialog disentanglement approaches and these findings would promote a better application of dialog disentanglement in software engineering.