Installation of nest boxes for a declining raptor species, the American Kestrel (Falco sparverius), in agricultural areas may benefit both local kestrel conservation and management of prey species that cause damage to crops. Kestrels responded quickly to the installation of 18 new nest boxes in northwestern Michigan cherry (Prunus spp.) orchards between 2012 and 2013; they made nesting attempts (laid eggs) in 100% of boxes by 2015. In addition, kestrels that made nesting attempts in these boxes in 2013–2015 showed high reproductive rates: apparent nesting success was 91%, and mean number of fledglings per box with nesting attempts was 3.8. Also, kestrels were highly tolerant of both traditional monitoring techniques (opening the box) and newer camera technologies (a pole-mounted video camera and nest-box video cameras). Generalized linear modeling indicated that variables related to nest monitoring techniques and effort did not significantly affect daily survival rates for nests or brood size at fledging for successful nests; only hatching date had a small positive effect on brood size at fledging. These results suggest that orchard nest boxes have the potential to sustain or increase the breeding kestrel population in the region while increasing kestrel predation of crop-damaging prey in and around cherry orchards. This is promising for ongoing and future work with nest boxes in agricultural regions.