Colorful plumage traits in birds may convey multiple, redundant, or unreliable messages about an individual. Plumage may reliably convey information about disparate qualities such as age, condition, and parental ability because discrete tracts of feathers may cause individuals to incur different intrinsic or extrinsic costs. Few studies have examined the information content of plumage in a species that inhabits forest canopies, a habitat with unique light environments and selective pressures. We investigated the information content of four plumage patches (blue-green crown and rump, tail white, and black breast band) in a canopy-dwelling species, the Cerulean Warbler (Setophaga cerulea), in relation to age, condition, provisioning, and reproduction. We found that older males displayed wider breast bands, greater tail white, and crown and rump feathers with greater blue-green (435–534 nm) chroma and hue than males in their first potential breeding season. In turn, older birds were in better condition (short and long term) and were reproductively superior to younger birds. We propose that these age-related plumage differences (i.e. delayed plumage maturation) were not a consequence of a life history strategy but instead resulted from constraints during early feather molts. Within age classes, we found evidence to support the multiple messages hypothesis. Birds with greater tail white molted tails in faster, those with more exaggerated rump plumage (lower hue, greater blue-green chroma) provisioned more, and those with lower rump blue-green chroma were in better condition. Despite evidence of reliable signaling in this species, we found no strong relationships between plumage and reproductive performance, potentially because factors other than individual differences more strongly influenced fecundity.