It has long been appreciated by systematists that the present polytypic species of Longbilled Pipit Anthus similis of the Afrotropics is composite, the populations inhabiting deciduous Miombo (Brachystegia) woodland south of the equator being specifically distinct from those of drier, more open and often mountainous terrain, to the south and northeast. Resolution of the complex requires the recognition of three species: the Longbilled Pipit Anthus similis Jerdon, the Wood Pipit A. nyassaeNeumann and Jackson's Pipit A. latistriatus Jackson in which a new subspecies is proposed. The African Richard's Pipit A. cinna-momeus Rüppell is marginally involved. The current complicated mosaic of sympatric polytypic species of the Miombo woodlands biome extending from western Zaïre and Angola, to southern Tanzania, Moçambique and Zimbabwe results from a situation in which specifically discrete descendants of a primary colonization are sympatric with populations of a lineage resulting from a second colonization. The ancestral stocks are considered to be of Eurasian origin. They have become modified in Africa since the Pleistocene by the interaction of climatic and vegetational oscillations, dieback, subspeciation and adaptive convergence. The Mountain Pipit A. hoeschi of the southeastern highland massif of Africa is seen as a remotely detached isolate stemming from the same ancestral stock as the contemporary Jackson's Pipit A. latistriatus. A revised systematic arrangement of the taxa involved in this enquiry is proposed.