Using recently developed pressure loading actuators (PLA), ramp and realistic fluctuating wind loads are applied to toe-nail connections which are typically used in wood-frame residential construction. The failure capacity from the ramp and fluctuating wind load tests are found to be similar, and are comparable to capacities reported in the literature. However, under realistic wind loading, the toe-nail connections are found to fail in increments with the majority of the damage to the connection occurring intermittently at the peak pressures so that it takes many peaks for a connection to fail. In addition, the effects of construction defects, in this case missing nails, were also examined in order to determine the reduction in capacity. Considering the wind loads on a typical house, estimates for failure wind speeds were obtained, assuming a factor of safety, and compared to ASCE 7-05 wind regions.