Community development is commonly described as contested practice, it is defined in many nuanced ways and there are challenges across the literature encouraging practitioners to engage more fully with critical thinking and transformative intent. The aim of this inquiry was to investigate community development practitioners’ perspectives on their practice in Scotland. Using an interpretivist framework, the research was designed to foreground the participants’ voices as experts on their own practice. Dyadic dialogical interviews were developed and used as community development inspired research methods and the participants’ perspectives are presented as dialogues interspersed with my analysis. The dialogues present community development practitioners who are highly reflective critical thinkers, articulate about the conceptual underpinnings of their approaches and fully aware of the socio-political contexts they are operating in. A complex picture is revealed of community development as clear, courageous, caring, critical, politically motivated practice that is grounded in ideological thinking, respect for people’s agency, and in mutual striving for transformative social change. The participants demonstrated a healthy awareness of limitations to practice and of the weight they carry in their engagement with the somewhat grand expectations of community development. Nonetheless the predominant thread throughout is of hopeful practice driven by an enduring commitment to tackling social inequalities and to striving to make society a better place combined with a profound belief this is possible. There is a sense of community development being portrayed as fragile practice in a context dominated by service provision and the conclusion is that it needs cared for as dynamic practice that has an important role to play in striving for positive social change.