Although reports of identity theft continue to be widely published, users continue to post an increasing amount of personal information online, especially within social networking sites (SNS) and e-learning systems (ELS). Research has suggested that many users lack awareness of the threats that risky online personal information sharing poses to their personal information. However, even among users who claim to be aware of security threats to their personal information, actual awareness of these security threats is often found to be lacking. Although attempts to raise users' awareness about the risks of sharing their personal information have become more common, it is unclear if users are unaware of the risks, or are simply unwilling or unable to protect themselves. Research has also shown that users' habits may also have an influence on their practices. However, user behavior is complex, and the relationship between habit and practices is not clear. Habit theory has been validated across many disciplines, including psychology, genetics, and economics, with very limited attention in IS. Thus, the main goal of this study was to assess the influence of users' personal information sharing awareness (PISA) on their personal information sharing habits (PISH) and personal information sharing practices (PISP), as well as to compare the three constructs between SNS and ELS. Although habit has been studied significantly in other disciplines, a limited number of research studies have been conducted regarding IS usage and habit. Therefore, this study also investigated the influence of users' PISH on their PISP within the contexts of SNS and ELS. An empirical survey instrument was developed based on prior literature to collect and analyze data relevant to these three constructs. Path analysis was conducted on the data to determine the influence of users' PISA on their PISH and PISP, as well as the influence of users' PISH on their PISP. This study also utilized ANCOVA to determine if, and to what extent, any differences may exist between users' PISA, PISH, and PISP within SNS and ELS. The survey was deployed to the student body and faculty members at a small private university in the Southeast United States; a total of 390 responses was received. Prior to final data analysis, pre-analysis data screening was performed to ensure the validity and accuracy of the collected data. Cronbach's Alpha was performed on PISA, PISH, and PISP, with all three constructs demonstrating high reliability. PISH was found to be the most significant factor evaluated in this study, as users' habits were determined to have the strongest influence on their PISP within the contexts of SNS and ELS. The main contribution of this study was to advance the understanding of users' awareness of information security threats, their personal information sharing habits, and their personal information sharing practices. Information gained from this study may help organizations in the development of better approaches to the securing of users' personal information.