Jared Diamond's argument against extraterrestrial intelligence from evolutionary contingency is subjected to critical scrutiny. As with the earlier arguments of George Gaylord Simpson, it contains critical loopholes that lead to its unraveling. From the point of view of the contemporary debates about biological evolution, perhaps the most contentious aspect of such arguments is their atemporal and gradualist usage of the space of all possible biological forms (morphospace). Such usage enables the translation of the adaptive value of a trait into the probability of its evolving. This procedure, it is argued, is dangerously misleading. Contra Diamond, there are reasons to believe that convergence not only plays an important role in the history of life, but also profoundly improves the prospects for search for extraterrestrial intelligence success. Some further considerations about the role of observation selection effects and our scaling of complexity in the great debate about contingency and convergence are given. Taken together, these considerations militate against the pessimism of Diamond's conclusion, and suggest that the search for traces and manifestations of extraterrestrial intelligences is far from forlorn. Key Words: Astrobiology-Evolution-Contingency-Convergence-Complex life-SETI-Major evolutionary transitions-Selection effects-Jared Diamond. Astrobiology 18, 491-502.