Oriented matroids are combinatorial structures that generalize point configurations, vector configurations, hyperplane arrangements, polyhedra, linear programs, and directed graphs. Oriented matroids have played a key role in combinatorics, computational geometry, and optimization. This paper surveys prior work and presents an update on the search for bounds on the diameter of the cocircuit graph of an oriented matroid. The motivation for our investigations is the complexity of the simplex method and the criss-cross method. We review the diameter problem and show the diameter bounds of general oriented matroids reduce to those of uniform oriented matroids. We give the latest exact bounds for oriented matroids of low rank and low corank, and for all oriented matroids with up to nine elements (this part required a large computer-based proof). For arbitrary oriented matroids, we present an improvement to a quadratic bound of Finschi. Our discussion highlights an old conjecture that states a linear bound for the diameter is possible. On the positive side, we show the conjecture is true for oriented matroids of low rank and low corank, and, verified with computers, for all oriented matroids with up to nine elements. On the negative side, our computer search showed two natural strengthenings of the main conjecture are false.