Stack Overflow is one of the prominent resources in the software community where developers seek technical assistance. Owing to its popularity, the platform witnesses questions of varying difficulty levels. Since not all practitioners are equally adept at addressing these queries, many queries remain unanswered or experience delays in receiving responses. However, the current framework of the site primarily categorizes the questions based on programming languages and specific topics, not considering the complexity level of the post. To bridge this gap, we introduce DATSO, a Difficulty Assessment Tool for Stack Overflow Questions. DATSO is a Chrome extension that assigns “difficulty level tags” to Stack Overflow posts by leveraging the textual and context-dependent features of the questions. Unlike previous works, which face issues like data imbalance and cold start problems, DATSO overcomes these limitations, achieving 72.3% accuracy on a benchmark dataset of Java questions, surpassing existing baseline works by 7%. The video demonstration and code repository can be found at https://youtu.be/VSu2Q0zb-X0 and https://github.com/krish10924/Difficulty-tag-Generator.