In forest operations, the interface between forest companies and harvesting contractors is of special importance, considering that it is the first link in the forest industry’s supply chains. Supply operations account for a significant share of the final costs of wood products (up to 50%). This study investigates the effect of customer–contractor alignment on contractors’ profit margins and on the risk for business relationship breakdown. Alignment is empirically measured for a Swedish forest company and 74 of its harvesting contractors, who were monitored during a four-year period. Two measures of alignment are employed: (1) the customer-perceived value of the contractors’ services; and (2) the contractors’ perceived alignment with the forest company expectations. Results indicate that the two measures of alignment are largely independent from each other, and that customer-perceived value affects both contractor profitability and the risk of relationship breakdown. Conflict between the two parties and lack of trust for the customer were found to be common complaints among contractors who ceased working for the studied forest company. Consequently, customer–contractor alignment should be considered a key objective by contractors who strive for business success, and also by forest companies who wish to improve their supply chain performance.