This chapter examines a therapeutic community programme as a holding environment, attempts to illustrate the value of some of D. W. Winnicott’s concepts in understanding unfolding clinical events, and considers the role of the setting as a system, the dynamics of which may lead to “failures” of holding. For seriously disturbed patients, a therapeutic community programme, enriched by a psychodynamic systems perspective, can provide an essential holding environment for treatment as well as remarkable depth of learning in itself. At the beginning of this therapeutic community’s psychoanalytic history, when burgeoning crises with patients were making it clear to senior staff that analytic neutrality was no way to administer a hospital, a “historic decision” was taken “to talk the situation over with the patients”. A holding environment both enriches the developmental process and contains its various elements toward their eventual integration. “The operation of setting factors” can be considered as an effort to understand the systemic dynamics of the holding environment.