Embodiments described herein are generally directed to training of classification models and their use by a chatbot to identify a customer-specified product support issue and provide appropriate troubleshooting guidance. According to an example, text describing an issue associated with a product line of a vendor is received via the chatbot. A vector representation of the issue is created using a word association model corresponding to the product line and trained based on a set of historical support cases relating to multiple supported issue categories for the product line. It is determined whether the issue matches a category within the supported issue categories for the product line by applying a classification model to the vector representation. When the determination is affirmative, an automated, interactive, conversational troubleshooting dialog is initiated with the user via the chatbot and guided based on a decision tree for the category within the product line.