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Stack Overflow accumulates an enormous amount of software engineering knowledge. However, as time passes, certain knowledge in answers may become obsolete. Such obsolete answers, if not identified or documented clearly, may mislead answer seekers and cause unexpected problems (e.g., using an out-dated security protocol). In this paper, we investigate how the knowledge in answers becomes obsolete and identify the characteristics of such obsolete answers. We find that: 1) More than half of the obsolete answers (58.4 percent) were probably already obsolete when they were first posted. 2) When an obsolete answer is observed, only a small proportion (20.5 percent) of such answers are ever updated. 3) Answers to questions in certain tags (e.g., node.js, ajax, android, and objective-c) are more likely to become obsolete. Our findings suggest that Stack Overflow should develop mechanisms to …