It is widely acknowledged that problem solving is one of today's prominent skills and is an ongoing activity where learners are actively involved in seeking information, generating new knowledge based on this information, and making decisions accordingly. In this respective, through infusing problem-solving into curriculum of language teaching, it might be possible to help students have responsibility for their own learning and learn a variety of ways to take personal actions to solve problems. In addition, problem-solving enables learners to link new knowledge with the real-life activities, leading to higher levels of thinking. Therefore, the current study aims to encourage learners to utilize problem-solving skills through "Quandary," an application used to create web-based action mazes. The participants include sixty-four prospective teachers of English at the Department of Foreign Language Education at a state university. After the training with hands-on experience on the use of the software, the participants were asked to create a situation related to language assessment and evaluation, together with a number of choices to select. Each resulting situation was required to be presented again with a set of options, leading to a kind of interactive case study where the reader was asked to decide and make decisions based on the presented information. Based on the interviews conducted with the participants, it was determined that the participants improved their problem-solving skills and linked the content of the course with situations. Moreover, the results indicated that quandary has proven to be an interesting means to stimulate the participants' motivation as well as curiosity and interest in the text-based situation.