Introduction of new technologies into the world is increasing rapidly, and 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 personnel is required by the IT industries 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.