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Have you checked the enrollment history? Is re enrollment turned on?

re-enrollment is on, enrollment history is empty

Hmm, maybe test a contact who meets the criteria and should enroll and see if HS agrees that they would enroll

test shows it should be working

The enrollment criteria is quite broad, I expect a couple thousand contacts should be matched, do you think that could be the issue?

If the enrollment history is empty I don't think it would hurt to turn the workflow off and back on again and see if HubSpot picks up the 1,000+ peopl...

Thanks for your help! I contacted HS support to see if they're able to help as well. I don't think it's the custom code, I suspect the workflow is sim...

it is able to match the contacts

I would select enroll contacts that meet the criteria, give it a minute and then check the enrollment history to see if it's working. Good luck!