Self-fertilization is classically thought to be associated with propagule dispersal because self-fertilization is a boon to colonizers entering environments devoid of pollinators or potential mates. Yet, it has been theoretically shown that random fluctuations in pollination conditions select for the opposite association of traits. In nature, however, various ecological factors may deviate from random variations, and thus create temporal correlation in pollination conditions. Here, we develop a model to assess the effects of pollination condition autocorrelation on the joint evolution of dispersal and self-fertilization. Basically, two syndromes are found: dispersing outcrossers and nondispersing (partial) selfers. Importantly, (1) selfers are never associated with dispersal, whereas complete outcrossers are, and (2) the disperser/outcrosser syndrome is favored (resp. disfavored) by negative (resp. positive) autocorrelation in pollination conditions. Our results suggest that observed dispersal/mating system syndromes may depend heavily on the regime of pollination condition fluctuations. We also point out potential negative evolutionary effects of anthropic management of the environment on outcrossing species.