Juggling work, personal responsibilities, and academic obligations can be challenging for many students, who work while studying, potentially leading to difficulties in adapting to the academic demands and compromising academic success. This study aims to evaluate the relationship between life domain (e.g., work, personal, and university) obstacles and academic adaptation among working university students in Estonia. Using the data from the Eurostudent-VII survey, the study estimated quantitative measures of association. The findings suggest that work-related issues negatively affect academic adaptation, while concerns related to childcare and the financial situation did not have any statistically significant impact. In contrast, issues with unsuitable and demanding academic programmes were found to significantly affect academic adaptation for working students. This study sheds light on the challenges faced by working students and the manner in which these obstacles can affect academic experiences, underscoring the need for support for employed university students in Estonia. Such knowledge can be put to further research use, and it can also inform initiatives aimed at assisting students, who are simultaneously working and pursuing higher education.