Horseweed [Conyza canadensis (L.) Cronquist] is a facultative winter annual weed that can emerge from March to November in Michigan. Fall-emerging C. canadensis overwinters as a rosette, while spring-emerging C. canadensis skips the rosette stage and immediately grows upright upon emergence. In Michigan, primary emergence recently shifted from fall to spring/ summer and therefore from a rosette to an upright growth type. Growth chamber experiments were conducted to determine (1) whether both C. canadensis growth types could originate from a single parent and (2) whether common environmental cues can influence growth type. Variations in temperature, photoperiod, competition, shading, and soil moisture only resulted in the rosette growth type in four C. canadensis populations originating from seed collected from a single parent of the upright growth type. However, a vernalization period of 4 wk following water imbibition, but before germination, resulted in the upright growth type. Dose–response experiments were conducted to determine whether glyphosate sensitivity differed between C. canadensis growth types generated from a single parent of the upright growth type. Upright-type C. canadensis from known glyphosate-resistant populations ISB-18 and MSU-18 were 4- and 3-fold less sensitive to glyphosate than their rosette siblings, respectively. Interestingly, differences in glyphosate sensitivity were not observed between growth types from the susceptible population. These results suggest that while C. canadensis populations shift from winter to summer annual life cycles, concurrent increases in glyphosate resistance could occur.