Examples of automated order troubleshooting are described. In an example embodiment, sales-specific data sources associated with at least one of a process, an organization, and an industry relevant for sales operations are monitored. From the monitored sales-specific data, an operation behavioral pattern is identified, based on predefined rules. Subsequently, a behavior model capturing the operation behavioral pattern is constructed using a pre-existing behavior model library. Using the behavior model, a potential event relating to an order received to be fulfilled using the sales operation is predicted, the potential event being indicative of an issue affecting the order. Accordingly, the issue affecting the order is proactively remediated to automatically troubleshoot the order.