Insects and flowering plants have rarely invaded the sea. Explanations for this have traditionally centered on the unique shortcomings of these groups in the marine environment. We show, however, that transitions among terrestrial, freshwater, and marine environments are infrequent in all major plant and animal clades except tetrapod vertebrates. In general, well-adapted incumbents are at a competitive advantage over would-be invaders from a physically different habitat. Data on the times and places of transition are consistent with our contention that evolutionary transitions among physically different environments are most likely when incumbents in the recipient environment exist in a regime of low-intensity competition and predation, as in terrestrial communities of the middle Paleozoic or the land biotas of oceanic islands. Freshwater environments, in which inferred intensities of predation are lower than in most marine and terrestrial environments, offer less biotic resistance to invaders than do communities in the sea or on land. Most invaders respond to novel physical circumstances by shutting down their metabolic machinery, and therefore add to their subordinate status as competitors with active incumbents. Only active tetrapods, particularly those with high and endothermically driven rates of metabolism, have successfully overcome this limitation.