Higher Education Institutions (HEIs) are complex societal entities that work and thrive in active and dynamic environments. There are many ways in which universities engage and interact with different entities. This chapter proposes HEIs’ community involvement activities provide the elements to fulfill their mission and purpose beyond teaching and research. To carry out such critical task, HEIs introduce new communication technologies and successfully developed innovative models; however, despite their relative success, relevant challenges exist including the core theoretical tenants sustaining engagement and current best practices. This chapter addresses such gap by exploring Multiple Stake Holder and Third Mission Theories. Practical instances of university community involvement from a Canadian perspective illustrate current best practice.