When setting up your workflow, you can choose if you'd like contacts to be re-enrolled in the workflow when they meet one of the re-enrollment triggers you select. However, re-enrollment based on some properties and filters is not supported.
For example, it is not possible to use a condition based on a contact property if the contact property can be equal to multiple values for re-enrollment, e.g., The contact property State/Region is equal to any of California, Colorado, or Connecticut. Also, some properties that are set automatically by HubSpot, such as Recent Conversion, cannot be used in re-enrollment triggers. Deal and company property filters are also not supported for re-enrollment.
Please note: the examples above are not exhaustive, and there may be additional filters and properties unavailable for re-enrollment. When setting up re-enrollment triggers, these unsupported conditions will appear under The following enrollment conditions can't be used for re-enrollment.
You can, however, create a smart list using the above logic and then enroll your contacts in the workflow based on that smart list. You will then be able to select your smart list as a condition for re-enrollment in your workflow.
Alternatively, you can create unique enrollment triggers for each value the property can be equal to using the OR filter as seen below.
You can then select each condition for re-enrollment.