Technical question and answer (Q&A) websites provide a platform for developers to communicate with each other by asking and answering questions. Stack Overflow is the most prominent of such websites. With the rapidly increasing number of questions on Stack Overflow, it is becoming difficult to get an answer to all questions and as a result, millions of questions on Stack Overflow remain unsolved. In an attempt to improve the visibility of unsolved questions, Stack Overflow introduced a bounty system to motivate users to solve such questions. In this bounty system, users can offer reputation points in an effort to encourage users to answer their questions.

In this paper, we study 129,202 bounty questions that were proposed by 61,824 bounty backers. We observe that bounty questions have a higher solving-likelihood than non-bounty questions. This is particularly true for long-standing unsolved questions. For example, questions that were unsolved for 100 days for which a bounty is proposed are more likely to be solved (55%) than those without bounties (1.7%).

In addition, we studied the factors that are important for the solving-likelihood and solving-time of a bounty question. We found that: (1) Questions are likely to attract more traffic after receiving a bounty than non-bounty questions. (2) Bounties work particularly well in very large communities with a relatively low question solving-likelihood. (3) High-valued bounties are associated with a higher solving-likelihood, but we did not observe a likelihood for expedited solutions.

Our study shows that while bounties are not a silver bullet for getting a question solved, they are associated with a higher solving-likelihood of a question in most cases. As questions that are still unsolved after two days hardly receive any traffic, we recommend that Stack Overflow users propose a bounty as soon as possible after those two days for the bounty to have the highest impact.