Embodiments described herein are generally directed to use of a chatbot to identify a customer-specified product support issue and provide appropriate troubleshooting guidance. According to an example, free text input describing an issue associated with a product line of a vendor is received from a user via a chatbot. A vector representation of the issue is created by tokenizing and vectorizing the free text input using a word association model corresponding to the product line. It is determined whether the issue matches at least one category within multiple issue categories for the product line by performing similarity scoring between the vector representation and multiple vectors created based on top words per issue category of the multiple issue categories. Responsive to an affirmative determination, an automated, interactive, conversational troubleshooting dialog is initiated with the user via the chatbot and guided based on a decision tree for the at least one category.