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A new species of tree snake Dipsadoboa montisilva Branch, Conradie & Tolley sp. nov. (Serpentes: Colubridae) is described from the ‘sky islands’ of Mount Mabu and Mount Ribáuè in northern Mozambique. Features of scalation, colour, body form and habitat distinguish the new species from other Dipsadoboa. This is supported by a phylogenetic analysis using one mitochondrial marker (cytochrome b) that shows the new Mozambican species is divergent from other sampled Dipsadoboa, including D. flavida and D. aulica, the only congeners known to occur in Mozambique. Morphologically, the new Dipsadoboa forms part of the D. werneri-shrevei complex from east and southeast Africa, but differs in having higher subcaudal counts, a different temporal pattern and only two supralabials entering the orbit. Phylogenetically, it occurs in a clade with D. shrevei and D. werneri. The status of D. shrevei in East Africa is reassessed, particularly in terms of the poorly-known Dipsadoboa shrevei kageleri from northern Tanzania. It is morphologically well defined from D. shrevei shrevei and utilises a different habitat. Although based on limited genetic data, it appears to be well-defined from typical D. shrevei and is accordingly raised to specific status. The only Tanzanian record for typical D. shrevei from Mtene, Rondo Plateau in southeast Tanzania is well isolated from the species’ range to the west (e.g. Zambia, Angola) and the published scalation features, particularly ventral counts, do not fully accord with D. shrevei. The Rondo Plateau population is treated as Dipsadoboa incerta sedis, and because we return D. shrevei to its binomial status, we can no longer consider D. shrevei as occurring in Tanzania. Biogeographically, the Rondo Plateau population may have a stronger affinity to the new Mozambican species. The discovery of isolated populations of the new species in mid-altitude forest remnants on Mt Mabu and Mt Ribáuè emphasizes the high conservation importance of the Mozambique forest ‘sky islands’ from which numerous other endemic new species have been recently discovered. These species are impacted by ongoing habitat destruction through slash and burn clearing for subsistence agriculture.