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Throughout Soviet history, individuals emerged who, while not necessarily opposing communism, harbored doubts about the system’s absolute ideological claims. This paper examines four intellectuals—Andrei Platonov, Varlam Shalamov, Aleksandr Solzhenitsyn, and Mikhail Heller—who navigated different political contexts yet shared a critical awareness of the system’s dysfunction. Their doubts, often expressed through culture and intellectual discourse, shaped their transformation from passive participants to outspoken critics of Soviet rule.