This study questioned the validity of the Global History and Geography Regents exam DBQ as an authentic learning event and assessment. The previous five years of the Global History and Geography Regents DBQs administered in June were evaluated to assess the authenticity of the documents in regards to their context, the level of questioning featured in the task and constructed response questions, and the readability levels of the documents. Ultimately the analysis of the data disproved the validity of the DBQ as an authentic task as presented in the Global History and Geography Regents. In the end, teachers must infuse their curriculum with both challenging texts and authentic tasks to prepare students in accordance to new Common Core Standards