Reenrollment and Webhooks not firing



Hi forum! I’ve been working with my dev team to enable some functionality around email opt-in/opt-outs and webhooks with our product.

Essentially we have a bi-directional situation going on where if someone unsubscribes from an email type in hubspot, it updates a field in our product, and vice-versa. However! It now seems that we have a situation where the workflow that we have setup to trigger this webhook is NOT working on the reenrollment of a contact.

Is there some internal logic that is hindering our webhooks from firing when a contact is reenrolled in a workflow that I have not found?

Thank you!


Hi @Chimp_Michael,

Without knowing the specifics of your Workflow configuration, its difficult to pinpoint the issue here. Are you able to share a link to the workflow? Feel free to shoot me a private message with the link.

Re-enrolment is controlled within the Workflow enrolement settings, as shown here in the UI ::

This modal is accessed by hitting the ‘Change’ link, highlighted in red. Please note that some conditions cannot be used for re-enrolement. Read more here.

Let me know how I can help further.


Hi @kfischmann,

I’ve tried it a few different ways, but the issue that my devs are encountering now is that the webhook itself is not firing. I’m wondering if there is a time delay before a workflow will trigger, in conjunction with some of this?

The issue is that the criteria for re-enrollment didn’t seem to be triggering properly because we wanted to trigger it on “If ‘Email type’ opt-out = No,” but when someone is Opted-in to an email type, it’s actually just shown as blank. When they ARE Opted-out, it shows as ‘Yes’.

*I have since changed this to “If Email Opt-Out = No” and was able to check the box that allowed for the criteria to be re-enrolled, but still weh ave a webhook issue.

Are we to assume that ‘blank’ is equal to ‘No’? Additionally, is there any reason a webhook would not fire, if the workflow was true, and re-enrollment was possible? Or is there a delay we need to be aware of?

Thank you,


So, actually the issue is a lot more simple than I originally understood.

The Workflow itself is not renrolling anyone, based on the criteria I have laid out. i.e. if opt-out is Yes >>> re-enroll in workflow #1 (and trigger webhook), if opt-out is No >>> re-enroll in workflow #2 (and trigger webhook).

However, even though the Opt-out property is being updated without issue via the email preferences located at the bottom of an email, that property being the trigger for the re-enrollment is not working.

Any thoughts on why this might be?