Previous research has revealed that students typically struggle with analytical writing, particularly if it deviates from the commonly taught "writing structure" (Murphree, 2014). This struggle is frequently coupled with a lack of understanding of course content materials, or the often-ambiguous nature of analysis in writing, which students typically do not encounter in a structured, standards-based classroom. The pressure surrounding these writing struggles is seemingly amplified in a rigorous, high-performing dual-enrollment high school setting where students are required to demonstrate proficiency in analytical ability and argumentative writing prior to their 10th grade year. This study aims to develop a more comprehensive model to teaching analytical writing by implementing a combination of a skills-based approach and an approach that promotes self-efficacy and meta-cognitive reflection. This combination seeks to not only alleviate anxiety and lack of confidence in the writing process, but also equip students with tools that can increase the accuracy of self-assessment and overall writing scores. The effect of metacognitive tools on student analytical writing in this study is measured primarily through student performance on a series of AP World History-style Document Based Question (DBQ) essays and academic confidence self-evaluation surveys. Data consists of outcomes from one baseline DBQ (prior to supplemental instruction) and outcomes from two DBQ essays after direct instruction of three metacognitive tools and the introduction of a series of surveys designed to promote self-efficacy. Each measure was cross analyzed based on the introduction of a series of three metacognitive strategies to aid in writing DBQs (Pre-write Graphic Organizer, Formatting Guide, and Peer Evaluation Tool) and compared to the baseline scores collected after the pre-intervention DBQ Assessment. Preliminary results indicate that average student confidence, as measured by self-efficacy surveys prior to each DBQ writing assignment, rose over time, with content-based confidence and overall DBQ scoring confidence exhibiting the greatest change. Students initially demonstrated a period of "false confidence" during their baseline assessment, followed by a dip (lack of confidence) and rise (increasing confidence) correlating with increased accuracy in scoring as time progressed. Students' ability to accurately predict their success on the DBQ rubric increased over time. However, the greatest improvement in this metacognitive skill can be observed in areas related to content knowledge.