Abstract — Introduction of new technologies in to the world is increasing rapidly and in order to assist the users to get equipped with such technologies industries are providing customer care services. Contacting a customer care service is subjective to several overheads of selecting options from a listed set, waiting for the switching between selections and awaiting the support of a customer care executive as the process usually requires a human intervention. Hence, a substitute for a personnel is required by the IT industries in order to automate the communication process in assisting the customers. Chatbots with context aware question-answering capabilities can be viewed as a good solution to such customer-care assistance. Development of a chatbot and the complexities involved in getting it to work effectively is delineated in this paper.