Currently, contacts must be manually re-enrolled in a workflow if the enrollment criteria includes a deal property (specifically, deal stage). The inability to automatically re-enroll is very limiting, as we want our processes to work as seamlessly for repeat customers as they do for new customers.
I’m Megan Legge, a product manager for HubSpot’s workflows tool. Thank you for your votes and comments. At this time there are no plans to develop this Idea. While this functionality was explored back in 2018, we found it was not feasible to implement with our current re-enrollment system, and unfortunately, that is still the case.
Instead, since then, we’ve put efforts toward enhancing deal, company, ticket, and quote workflows to be more robust, and enable re-enrollment for all objects in their respective workflow types (ie. you can re-enroll a company in a company workflow via company centered criteria) and enhancing re-enrollment capabilities in each. For example, rolling date range centered criteria are now supported for re-enrollment. For example, this means you can re-enroll a deal into a deal workflow, using re-enrollment criteria such as, "Deal close date is less than X days from now."
Additionally, it sounds like a lot of these needs are rooted in cross-object property value setting/copying. To improve that experience, we’ve also introduced additional property management functionality via our contact workflows upgrade, over the past several months. For example, in contact workflows, you can now set & copy property values to all other objects (companies, deals, tickets and quotes) in the same way you've always been able to in the other workflow types.