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This paper discusses the prerequisites for the successful timing of firms' capital market activities (a.k.a. managerial market timing) and delineates the relevant laws and regulations. U.S. and German regular and ad-hoc reporting requirements, insider trading laws, and the enforcement of those are compared based on actual laws and regulations and existing research. The aim of the contribution is to determine the playground for exploiting superior information by firm management. This regulatory or legal playground is important to understand to assess firm management's actions in light of (potential) costs and benefits. It is demonstrated that – although having different approaches and histories regarding the regulatory framework of insider trading – Germany and the U.S. both prohibit insider trading. Thus, theoretically, observable successful market timing must be based solely on the market's misinterpretation of available information. Not always perfect enforcement of the ban on insider trading, and difficulties in proving when material information was first available to decision-makers might allow for assuming that the mispricing of already published information is not the only value driver…