The transparency of social Web paves the way for user‐generated content (UGC) to become a trusted form of brand communication. Research offers little guidance on UGC and trust development in social networking sites (SNS) and has yet to debate the effects of ad‐skepticism in the context of UGC and SNS. This study builds on theory to develop a conceptual framework that yields insights into the development of consumer trust toward user‐generated brand recommendations (UGBR). A set‐theoretic approach using fuzzy set qualitative comparative analysis is applied to data derived from 303 consumers. The study findings suggest that high levels of trust in UGBR are associated with high levels of trust toward Facebook friends and provide support for the moderating role of ad‐skepticism. Benevolence and integrity are found to be necessary/core conditions for the development of trust toward Facebook friends. Ability and disposition to trust are of peripheral importance. The significance of the findings and their implications are discussed.