Training can modify the visual system to produce a substantial improvement on perceptual tasks and therefore has applications for treating visual deficits. Visual perceptual learning (VPL) is often specific to the trained feature, which gives insight into processes underlying brain plasticity, but limits VPLs effectiveness in rehabilitation. Under what circumstances VPL transfers to untrained stimuli is poorly understood. Here we report a qualitatively new phenomenon: intrinsic variation in the representation of features determines the transfer of VPL. Orientations around cardinal are represented more reliably than orientations around oblique in V1, which has been linked to behavioral consequences such as visual search asymmetries. We studied VPL for visual search of near-cardinal or oblique targets among distractors of the other orientation while controlling for other display and task attributes, including task precision, task difficulty, and stimulus exposure. Learning was the same in all training conditions, however, transfer depended on the orientation of the target, with full transfer of learning from near-cardinal to oblique targets but not the reverse. To evaluate the idea that representational reliability was the key difference between the orientations in determining VPL transfer, we created a model that combined orientation-dependent reliability, improvement of reliability with learning, and an optimal search strategy. Modeling suggested that not only search asymmetries but also the asymmetric transfer of VPL depended on preexisting differences between the reliability of near-cardinal and oblique representations. Transfer asymmetries in model behavior also depended on having different learning rates for targets and distractors, such that greater learning for low-reliability distractors facilitated transfer. These findings suggest that training on sensory features with intrinsically low reliability may maximize the generalizability of learning in complex visual environments.