Automated detection of software vulnerabilities is a fundamental problem in software security. Existing program analysis techniques either suffer from high false positives or false negatives. Recent progress in Deep Learning (DL) has resulted in a surge of interest in applying DL for automated vulnerability detection. Several recent studies have demonstrated promising results achieving an accuracy of up to 95 percent at detecting vulnerabilities. In this paper, we ask, “how well do the state-of-the-art DL-based techniques perform in a real-world vulnerability prediction scenario?” To our surprise, we find that their performance drops by more than 50 percent. A systematic investigation of what causes such precipitous performance drop reveals that existing DL-based vulnerability prediction approaches suffer from challenges with the training data (e.g., data duplication, unrealistic distribution of vulnerable classes, etc.) and with the model choices (e.g., simple token-based models). As a result, these approaches often do not learn features related to the actual cause of the vulnerabilities. Instead, they learn unrelated artifacts from the dataset (e.g., specific variable/function names, etc.). Leveraging these empirical findings, we demonstrate how a more principled approach to data collection and model design, based on realistic settings of vulnerability prediction, can lead to better solutions. The resulting tools perform significantly better than the studied baseline—up to 33.57 percent boost in precision and 128.38 percent boost in recall compared to the best performing model in the literature. Overall, this paper elucidates existing DL-based vulnerability prediction systems’ potential issues and draws a roadmap for future DL-based vulnerability prediction research.