This research examines whether changes in the regulatory environment (Plain English Guidelines, Reg. FD and SOX), management pessimism, and meeting/beating or missing analyst forecasts have had an impact on earnings disclosure readability over the 1997-2007 timeframe and whether firm managers are able to make negative firm financial information less transparent to the market by making negative earnings disclosures less readable. The idea that management may attempt to reduce the impact of bad news by making it more costly to analyze is not new. However, studying the qualitative aspects of the unaudited earnings disclosures is a unique setting and extends previous work on annual report readability. This study finds that the Plain English Guidelines, Reg. FD and SOX had differential impacts on earnings disclosure readability. Additionally, it finds that earnings disclosure readability decreases as firm earnings decrease. Moreover, this study demonstrates that institutional investors contribute to earnings disclosure readability and may serve as monitors of management in this regard. Finally, firms that beat analyst forecasts have more readable earnings disclosures. This study not only contributes to the body of academic literature, but also informs regulators regarding their ability to induce firm management to write more informative earnings disclosures.