While codes of ethical conduct are important, they do not always fit neatly in the organic community settings in which some workers engage. Professional standards from accrediting bodies are easy to sign up to, yet much more difficult to put into practice. Drawing upon community connection practice in recovery-oriented mental health work, this article names the professional boundary tensions peculiar to less structured fields of engagement. We suggest that for workers in these fields, there has been a disconnection between the theory, the experience, and the public discourse of professional boundaries. We argue that such disconnection can create uncertainty, anxiety, and secrecy, creating exactly those cultures we wish to avoid. Ultimately this leads to greater harm for vulnerable individuals, as well as the workers and organisations that serve them. The alternative is to engage in what we name a “risky conversation,” to expose this disconnect and engender a new type of professionalism.