The British Tree Pipit Anthus trivialis population has shown a marked decline in recent decades, together with a range contraction that has been most apparent in central and southeast England. In East Anglia, the species is now largely restricted to heathland and, in particular, the conifer plantations established on light soils in these areas. Here I evaluate how Tree Pipits are influenced by the age of pine restock and the patchiness of habitat in Thetford Forest in the Breckland area of Norfolk and Suffolk, eastern England. Both the probability of occurrence and the densities of territory-holding Tree Pipits varied according to the age of coupes of restock – densities peaking in restock 1–6 years old – and were also significantly higher in coupes (a stand comprising one or more forest subcompartments planted in the same year, usually with the same tree crop) in the largest, most central forest block than in smaller, isolated blocks peripheral to this. Within coupes, the distribution and thus densities of Tree Pipits were limited by the availability of songposts. Few songflights finished on the ground or in flight and displaying birds only perched on restock once trees were at least 3 years old (0.8 m high) – thus, territories were only established away from bordering or retained mature trees once restock had reached this age. Pairing success was reduced among males with territories of less than 1 ha, as found in the highest densities in restock, but was unrelated to the proportion of songflights that individuals finished on perches. Thus, although the availability of songposts limited the distribution of the species, it did not appear to affect individual breeding success. The study highlights the importance of pine plantations for the species in lowland England, but also the benefits of large blocks of habitat and targeted forest management, for instance, the retention of mature trees in coupes of restock for Pipits to use as songposts.