Bees frequently forage in habitats with cluttered, wind-blown vegetation. Collisions with clutter and other obstacles can cause irreversible wing damage that impairs future flight performance and leads to mortality. We know little about the strategies that bees use to protect their wings when transiting narrow gaps between obstacles, like those in cluttered vegetation. We tested how the Valley Carpenter Bee Xylocopa varipuncta protects its wings while transiting a dynamic obstacle course that mimicked wind-blown vegetation, using a factorial design that varied obstacle motion (stationary or moving) and wind (still air, head- or tailwinds). We filmed bees flying through obstacle fields with gaps that were approximately equal to their wingspan, and quantified flight speed, yaw angle (relative to flight tunnel axis), and number of wing collisions with obstacles. Bees often increased their body yaw (i.e. turned sideways) during transits, and larger yaw angles were associated with fewer wing collisions. Bees reached higher maximum yaw angles when transiting stationary obstacles or when flying in still air, and as a result, they experienced fewer wing collisions in these conditions. On average, bees maintained similar ground speeds across all wind and obstacle conditions, but trials with faster ground speeds were associated with more wing collisions, possibly because bees had less time to turn their bodies before transiting the obstacles. When controlling for variation in body yaw and ground speed, there were similar numbers of wing collisions across all obstacle and wind conditions. This suggests that the high rate of wing collisions associated with wind and obstacle motion is driven mostly by the extent to which these conditions prevent bees from enacting their strategy of yawing to avoid wing damage.