Despite a robust and growing job market and lucrative salaries, there is a global shortage of Information Technology (IT) professionals. To make matters worse, women continue to be underrepresented in the IT workforce and among IT degree holders. In today’s knowledge based economy and society, it is extremely important to increase the presence of women in the IT field. In order to do so, it is necessary to reduce entry barriers and attract more women to pursue degrees in various IT fields including the field of Management Information Systems (MIS). Even though MIS is considered to have a more feminine nature, women still tend to avoid majoring in this field. Unfortunately, there is a lack of research that investigates the specific factors that may deter women from pursuing a degree in MIS. To address this research gap, this study examined a set of key environmental barriers that might prevent women from pursuing an MIS degree and explored whether there were any gender differences between female and male students in terms of these key barriers. Based on a survey of 280 students enrolled in an introductory level MIS course, the study empirically confirmed that there were significant differences between male and female students in terms of the key contextual barriers perceived. Female students demonstrated major concerns about gender discrimination related barriers, whereas male students were more concerned about negative social influences. Both male and female students were equally concerned about not being able to fit in well with other MIS majors. The findings have important implications for MIS programs, as the information gained can be used to design and implement specific intervention strategies to overcome the barriers and attract larger pools of women to the MIS discipline. The paper concludes with a discussion of the findings, implications, and future research directions.