The dissertation is structured as follows. In Chapter 2, I will review a) related literature on informal communication and its role in organizations, b) informal communication under a newly widespread form of remote communication: hybrid meetings and the power dynamics embedded in them, as well as c) efforts and challenges to support informal communication. Chapter 3 and 5 will present two qualitative studies. Study one (Chapter 3) used semi-structured, in-depth interviews to uncover detailed processes and examples of initiating and maintaining informal conversations remotely. A prototype was then built in Chapter 4 incorporating the interview insights; it is a Zoom video conferencing interface that allows users in one breakout room to be aware of what is happening in another breakout room through real-time video, auto-captioning, and sentiment analysis, and switch to another conversation when they wish too. Study two (Chapter 5) first conducted an observational study of 30 hybrid meetings of varied sizes to discover real world instances and factors that led to (lack of) cross-space interactions. To complement the observation data, I conducted 25 in-depth, semi-structured interviews to further explore motivations for (lack of) cross-space interactions and gather a wider range of examples from different types of organizations and meetings.After gaining a deeper understanding of how informal communication was (not) initiated in fully remote and hybrid contexts, in Chapter 6, I present design implications, discuss the results and findings, and propose future directions to support remote informal communication in more effective and creative ways.