Re-establishing connectivity between protected areas isolated by habitat clearing is a key conservation goal in the humid tropics. In northeastern Costa Rica, payments for environmental services (PES) and a government ban on deforestation have subsidized forest protection and reforestation in the San Juan–La Selva Biological Corridor (SJLSBC), resulting in a decline in mature forest loss and the expansion of tree plantations. We use field studies and graph models to assess how conservation efforts have altered functional connectivity over the last 25 years for four species of insectivorous understory birds. Field playback studies assessed how reforestation habitat quality affected the willingness of Myrmeciza exsul, Henicorhina leucosticta, Thamnophilus atrinucha, and Glyphorynchus spirurus to travel outside forest habitat for territorial defense. Observed travel distances were greatest in nonnative and native tree plantations with high understory stem density, regardless of overstory composition. In contrast, tree plantations with low stem density had travel responses comparable to open pasture for three of the four bird species. We modeled landscape connectivity for each species using graph models based on varying possible travel distances in tree plantations, gallery forests, and pastures. From 1986 to 2011, connectivity for all species declined in the SJLSBC landscape (5825 km2) by 14% to 21% despite only a 4.9% net loss in forest area and the rapid expansion of tree plantations over 2% of the landscape. Plantation placement in the landscape limited their potential facilitation of connectivity because they were located either far from forest cover or within already contiguous forest areas. We mapped current connectivity bottlenecks and identified priority areas for future reforestation. We estimate that reforestation of priority areas could improve connectivity by 2% with only a 1% gain in forest cover, an impressive gain given the small area reforested. Results indicate key locations where spatial targeting of PES within the SJLSBC study region would protect existing forest connectivity and enhance the connectivity benefits of reforestation.