Uncertainty in the implementation and outcomes of conservation actions that is not accounted for leaves conservation plans vulnerable to potential changes in future conditions. We used a decision-theoretic approach to investigate the effects of two types of investment uncertainty on the optimal allocation of global conservation resources for land acquisition in the Mediterranean Basin. We considered uncertainty about (1) whether investment will continue and (2) whether the acquired biodiversity assets are secure, which we termed transaction uncertainty and performance uncertainty, respectively. We also developed and tested the robustness of different rules of thumb for guiding the allocation of conservation resources when these sources of uncertainty exist. In the presence of uncertainty in future investment ability (transaction uncertainty), the optimal strategy was opportunistic, meaning the investment priority should be to act where uncertainty is highest while investment remains possible. When there was a probability that investments would fail (performance uncertainty), the optimal solution became a complex trade-off between the immediate biodiversity benefits of acting in a region and the perceived longevity of the investment. In general, regions were prioritized for investment when they had the greatest performance certainty, even if an alternative region was highly threatened or had higher biodiversity value. The improved performance of rules of thumb when accounting for uncertainty highlights the importance of explicitly incorporating sources of investment uncertainty and evaluating potential conservation investments in the context of their likely long-term success.