Moving Target (MT) defenses have been proposed as a gamechanging approach to rebalance the security landscape in favor of the defender. MT techniques make systems less deterministic, less static, and less homogeneous in order to increase the level of effort required to achieve a successful compromise. However, a number of challenges in achieving effective movement lead to weaknesses in MT techniques that can often be used by the attackers to bypass or otherwise nullify the impact of that movement. In this paper, we propose that these challenges can be grouped into three main types: coverage, unpredictability, and timeliness. We provide a description of these challenges and study how they impact prominent MT techniques. We also discuss a number of other considerations faced when designing and deploying MT defenses.