Background:The influence of policy on the incidence of human-wildlife conflict can be complex and not entirely anticipated. Policies for managing bear hunter success and depredation on hunting dogs by wolves represent an important case because with increasing wolves, depredations are expected to increase. This case is challenging because compensation for wolf depredation on hunting dogs as compared to livestock is less common and more likely to be opposed. Therefore, actions that minimize the likelihood of such conflicts are a conservation need.Methodology/Principal Findings:We used data from two US states with similar wolf populations but markedly different wolf/hunting dog depredation patterns to examine the influence of bear hunting regulations, bear hunter to wolf ratios, hunter method, and hunter effort on wolf depredation trends. Results indicated that the ratio of bear hunting permits sold per wolf, and hunter method are important factors affecting wolf depredation trends in the Upper Great Lakes region, but strong differences exist between Michigan and Wisconsin related in part to the timing and duration of bear-baiting (i.e., free feeding). The probability that a wolf depredated a bear-hunting dog increases with the duration of bear-baiting, resulting in a relative risk of depredation 2.12-7.22× greater in Wisconsin than Michigan. The net effect of compensation for hunting dog depredation in Wisconsin may also contribute to the difference between states.Conclusions/Significance:These results identified a potential tradeoff between bear hunting success and wolf/bear-hunting dog conflict. These results indicate that management options to minimize conflict exist, such as adjusting baiting regulations. If reducing depredations is an important goal, this analysis indicates that actions aside from (or in addition to) reducing wolf abundance might achieve that goal. This study also stresses the need to better understand the relationship among baiting practices, the effect of compensation on hunter behavior, and depredation occurrence.