The prevailing view that SMEs embracing entrepreneurial risk-taking are likely to exhibit better export performance than those who don’t may be overly simplistic because (a) the payoffs to risk taking are dependent upon the uncertainty in which the organization operates and (b) risk-taking may also be associated with higher probability of failure because SMEs usually lack slack resources that might otherwise serve to buffer negative outcomes. Drawing on prior research we hypothesize that risk-taking orientation and resource availability will have a positive (direct) impact on export performance. We simultaneously consider how environmental uncertainty, resource availability and entrepreneurial risk-taking orientation collectively contribute to performance and hypothesize that the same configurations that contribute to better performance among surviving firms are also associated with higher probability of failure.