Background: Software security is crucial to ensure that the users are protected from undesirable consequences such as malware attacks which can result in loss of data and, subsequently, financial loss. Technical Debt (TD) is a metaphor incurred by suboptimal decisions resulting in long-term consequences such as increased defects and vulnerabilities if not managed. Although previous studies have studied the relationship between security and TD, examining their intersection in developers' discussion on Stack Overflow (SO) is still unexplored. Aims: This study investigates the characteristics of security-related TD questions on SO. More specifically, we explore the prevalence of TD in security-related queries, identify the security tags most prone to TD, and investigate which user groups are more aware of TD. Method: We mined 117,233 security-related questions on SO and used a deep-learning approach to identify 45,078 security-related TD questions. Subsequently, we conducted quantitative and qualitative analyses of the collected security-related TD questions, including sentiment analysis. Results: Our analysis revealed that 38% of the security questions on SO are security-related TD questions. The most recurrent tags among the security-related TD questions emerged as “security” and “encryption.” The latter typically have a neutral sentiment, are lengthier, and are posed by users with higher reputation scores. Conclusions: Our findings reveal that developers implicitly discuss TD, suggesting developers have a potential knowledge gap regarding the TD metaphor in the security domain. Moreover, we identified the most common security topics mentioned in TD-related posts, providing valuable insights for developers and researchers to assist developers in prioritizing security concerns in order to minimize TD and enhance software security.

Background: GitHub is a collaborative platform for global software development, where Pull Requests (PRs) are essential to bridge code changes with version control. However, developers often trade software quality for faster implementation, incurring Technical Debt (TD). When developers undertake reviewers’ roles and evaluate PRs, they can often detect TD instances, leading to either PR rejection or discussions. Aims: We investigated whether Pull Request Comments (PRCs) indicate TD by assessing three large-scale repositories: Spark, Kafka, and React. Method: We combined manual classification with automated detection using machine learning and deep learning models. Results: We classified two datasets and found that 37.7 and 38.7% of PRCs indicate TD, respectively. Our best model achieved F1 = 0.85 when classifying TD during the validation phase. Conclusions: We faced several challenges during this process, which may hint that TD in PRCs is discussed differently from other software artifacts (e.g., code comments, commits, issues, or discussion forums). Thus, we present challenges and lessons learned to assist researchers in pursuing this area of research.