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In the educational domain, artificial intelligence (AI) is one of the information and communication technologies gaining popularity for its advantages in teaching and learning, especially in information support services. The University of the Philippines Open University (UPOU), as a leader of open and distance e-learning in the country, explored this technology and came up with its own tool to streamline its information support services. The UPOU chatbot, personified as Iska and IskOU, provides immediate and appropriate human-like conversations when prompted by users. The tool is able to deliver these conservations through its intelligence database or knowledge base, which is a result of a university-wide effort to collate relevant information. This chatbot intelligence influences user satisfaction as it is the basis of the tool’s performance. Therefore, the study aimed to evaluate the UPOU chatbot’s performance as an information support tool by determining the level of satisfaction of UPOU chatbot users. Data was collected through a post-interaction survey with the users and was analyzed using descriptive statistics and thematic analysis. Results showed mixed experiences among UPOU chatbot users. It was mainly reported that the tool has issues in interpretations and addressing complex, multiple, and specific/unique queries. Nonetheless, users evaluated the UPOU chatbot as a satisfying and helpful tool. A number of areas and topics for future investigations were also listed.