This study discusses the role of Board Monitoring Effectiveness (BME) on managers’ decisions regarding the business strategies that fit the external business environmental conditions by using a contingency analysis approach. Furthermore, this study will examine how fit strategies affect Sustainability Reporting (SR) of listed companies on the Indonesia Stock Exchange (IDX) from 2014 to 2017. This study uses Conditional Mixed Process (CMP) technique. This CMP method is claimed to be more efficient in analyzing the TSL models. This study found that in highly uncertain conditions, BME had a positive influence on the probability of managers to choose prospector and defender strategies rather than analyzers. These results indicate that BME shows positive impact on the contingency fit between business strategies and environmental uncertainty. In addition, the study documents that only prospectors have a positive impact on SR, however this study failed to document that defenders have positive impact on SR. Meanwhile the unexpected result is analyzers have a significantly positive effect on SR. This study is the first study to investigate the role of BME in contingency fit between business strategies and environmental uncertainties and how it produces effects up to the level of SR.