College is a time of transition, marked by new independence and challenges. Researchers were keen to understand college adjustment by examining key factors for students throughout their undergraduate programs. The Wooster-Wickline College Adjustment Test (WOWCAT) was developed as a more accessible alternative to clinical measures, improving existing research around college adjustment. Conducted during pre-pandemic, pandemic, and post-pandemic periods, this study analyzed students' academic year in school (first year, sophomore, junior, senior) alongside study habits and anxiety levels. The findings revealed a significant difference in study habits for students as they advanced in college. However, no significant differences in anxiety levels were observed based on the academic year. These findings aligned with previous research in this study area, emphasizing the nuanced nature of college adjustment. The study promotes the necessity for continued research to understand better and support students during this pivotal time of life.