Woodland birds are a species assemblage of conservation concern, and their persistence in fragmented agricultural landscapes is dependent on both the preservation of existing woodland remnants and the implementation of restoration plantings. However, little is known about the habitat‐use and persistence of birds in fragmented agricultural landscapes. We present a detailed, population‐oriented study of woodland birds in temperate eucalypt woodland restoration plantings and remnant woodland patches in the South‐west Slopes bioregion of New South Wales, Australia. First, we undertook a three‐year mark‐recapture project to assess annual survival and site fidelity in restoration plantings and woodland remnants. We supplemented our recapture efforts with resightings of colour‐banded individuals. Second, we tracked individual birds of two species – superb fairywren (Malurus cyaneus) and willie wagtail (Rhipidura leucophrys) – and documented snapshots of their home ranges and movement patterns during the breeding season. Annual survival in the woodland bird assemblage was lower than expected (51%). Home ranges of the superb fairywren were positively correlated with patch size, and were constrained by patch edges in linear sites. Superb fairywrens and willie wagtails were more likely to travel longer distances between substrates while foraging in linear sites. Willie wagtails engaged in significant gap‐crossing (up to 400 m) between adjacent habitat patches. Our findings indicate that 1) patch isolation and certain patch configurations place resident birds at an energetic disadvantage, and 2) in our study area, woodland bird populations are continuing to decline. We recommend landscape‐scale habitat restoration programs aim to address ongoing population declines. Studies such as ours conducted over longer time periods would provide a deeper understanding of habitat‐use and population processes of woodland birds in fragmented agricultural landscapes.