A key selection pressure in most habitats is predation, and a common strategy adopted by prey is crypsis through background matching. Many marine blenny fishes are in the process of a dramatic transition across one of the world's most extreme ecotones: the invasion of land across the intertidal zone. We investigated the impact of this transition on body crypsis versus the conspicuousness of visual signals across 56 blenny taxa relative to 59 biologically relevant backgrounds, as viewed by conspecifics and four representative fish and avian predators. We computed 33 colour and 23 pattern indices from standardised digital photographs of six individuals for each taxa (median sample). Six of these indices were selected for detailed analysis following phylogenetic Principal Component Analysis. While phylogenetic regressions revealed some aspects of body crypsis appeared to have changed adaptively with the progressive transition to land (specifically a reduction in body colour saturation), colonisation was primarily facilitated by a generalist form of crypsis. That is, the colours and patterns of aquatic blennies were already well matched to the range of terrestrial backgrounds where amphibious and terrestrial species were observed out of water. Predation appears to have been an important selection pressure constraining the colour and pattern of the dorsal fins used in social communication, which also matched visual backgrounds. Our data implies anti-predator strategies that translate well across habitats and different predator regimes will facilitate colonisation by either reducing predation risk or allowing species to persist long enough to respond adaptively to environmental change.