The question of when bidirectional heuristic search outperforms unidirectional heuristic search has been revisited numerous times in the field of Artificial Intelligence. This paper re-addresses the question of when bidirectional search outperforms unidirectional search using an updated theoretical understanding of the problem. We show that a core set of critical states in the state space are the primary factor determining whether a bidirectional search can outperform a unidirectional search and provide simple measures to determine whether a state space and heuristic contains these critical states. We similarly discuss and show the impact that asymmetry in the underlying problem graph has on the performance of bidirectional algorithms. Experimental results show the impact of these factors on whether a problem should be solved using unidirectional or bidirectional search.