Considering the complex structure of commercial insurance programs—typically purchased in annual “towers” of insurance—risk managers and in-house counsel often do not pay sufficient attention to arbitration-related provisions, which the insurance industry is more frequently including in its policies. That’s like playing only one board in a game of three-dimensional chess. Discrepancies among such provisions can lead to obstacles policyholders later must surmount when coverage disputes arise. This article highlights critical issues to consider and offers recommendations to avoid these obstacles wherever possible.