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This article compares surveillance-related experiences and attitudes of two generations of media users in countries with different historical surveillance regimes (Estonia, Portugal, and Sweden) and analyzes the predictors of the attitudes toward contemporary surveillance. A large-scale online survey (N = 3221) reveals that attitudes toward online state and corporate surveillance are interrelated; the two attitudinal components are, however, generation-specific, having different predictors. Tolerance toward state surveillance is more characteristic of the older group, being predicted by trustful and obedient attitudes toward state authorities and institutions. Tolerance toward corporate dataveillance is more characteristic of the younger group, being predicted by active and self-confident media use. While the socio-historical context molds the intergenerational gaps in surveillance-related experiences and attitudes, individual-level experiences of state surveillance do not predict tolerance toward either type of contemporary surveillance, suggesting that global techno-cultural developments are probably more powerful factors than past experiences in forming generation-specific attitudes. [ABSTRACT FROM AUTHOR]