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Telephone fundraising (telefundraising) is a for-profit industry employed by some US non-profit organizations (NPOs). Scant sociological research has been conducted of this relationship. While telefundraising’s influence may have diminished with the rise of caller identification technology and other communications options, it remains an element of NPO financing. It sustains a split between the ideals of NPOs which use it and telefundraising companies’ capitalist mandate to be profitable. This paper examines evidence of this split through: (1) how the industry orchestrates the social interaction between the caller and the call recipient (hereafter, “prospect”) in order to maximize its corporate profitability and NPO donations; (2) how telefundraising workers (hereafter, “callers”) negotiate fundraising conversations in the absence of signals available during face-to-face encounters; and (3) how techniques utilized by callers often contradict standards which NPO fundraising professionals claim they demand for these solicitations. Within this practice, contradictory pressures and commitments to fundraising and money-making become evident. As such, it can illuminate dilemmas at the intersection of American welfare capitalism and some nonprofit organizations that advocate left-liberal reforms, at the same time as these nonprofits gather resources by taking part in a profit-maximizing repertoire of behaviors and sentiments.