One of the major health benefits attributed to the ingestion of cranberry juice is the maintenance of urinary tract health. Traditionally, the juice was thought to cause acidification of the urine resulting in a bacteriostatic effect. However, recent research has demonstrated that a bacterial antiadhesion mechanism is responsible. Proanthocyanidins with unique molecular structures have been isolated from cranberry fruit that exhibit potent bacterial antiadhesion activity. Little is known about the bioavailability and structure-activity relationships of cranberry proanthocyanidins. Data on how certain structural features of the molecules can influence bioactivity and bioavailability are reviewed.