How to create looping workflows in HubSpot
Learn how to re-enroll contacts weekly for recurring emails without breaking your automation.
Question: I have a weekly reminder email that I’d like certain contacts to receive every Friday. How can I build a workflow that re-enrolls them weekly so they keep getting the email?
Out of the box, HubSpot doesn’t support workflows that run endlessly in a loop.
A record can only move through a workflow once, unless it continues to meet the enrollment criteria or you explicitly enable re-enrollment.
That’s intentional! Unchecked loops can flood contacts with unwanted messages, clutter your reporting, and create difficulty for your team.
That said, for predictable, recurring use cases like a weekly reminder email, there’s a safe workaround. The idea is to use two workflows that toggle a property back and forth.
- One workflow handles the sending and disables the property,
- The second flips the property back on, making the contact eligible again.
The two-fold workaround explained
To build a clean weekly loop, start by creating a simple property that will act as your trigger.
This property becomes the switch that alternates between “yes, send this person the email” and “no, hold off until next cycle.”
The process looks like this:
- Create a checkbox/contact property
Build a custom contact property (checkbox type) called something like “Weekly Email Flag.” This will serve as the on/off switch for enrollment. - Workflow A (Send & Disable)
- Enrollment criteria: contact meets your base conditions and the “Weekly Email Flag” = Yes.
- Add a delay to line the send up with the correct day and time (e.g., Friday morning).
- Add a “Send Email” action for the reminder message.
- Reset the flag by setting “Weekly Email Flag” = No.
- Turn on re-enrollment so contacts can come back through this workflow.
- Workflow B (Re-Enable)
- Enrollment criteria: contact meets the same base conditions and the “Weekly Email Flag” = No.
- Add a property update to set “Weekly Email Flag” = Yes.
- Enable re-enrollment here too.
With both workflows active, contacts bounce back and forth: A sends the email and flips the switch off, B flips the switch back on, and the cycle continues.
Things to know about re-enrollment
HubSpot places limits on what can and can’t trigger re-enrollment.
Property changes generally qualify, but activity-based triggers (such as “clicked an email” or “filled out a form”) cannot re-enroll a record once it’s already in the workflow.
That’s why a dedicated property like Weekly Email Flag works well for this pattern.
It’s also important to remember that a record cannot re-enter a workflow if it is still active in it. Your delays and toggles need to be designed so that the contact has exited before the re-enrollment condition is checked again. Without that timing, the loop will break.
Official documentation is clear on this: re-enrollment must be explicitly enabled in the workflow settings, and the record must meet both the original enrollment triggers and the re-enrollment condition for it to work. (HubSpot knowledge base reference)
Practical tips for running looping workflows
While the setup is fairly straightforward, execution can get messy if you don’t build guardrails.
A few best practices help keep it safe:
- Use delays that anchor the email to the exact day and time you want it sent. HubSpot’s “Delay until a day or time” feature is perfect for weekly reminders.
- Keep naming conventions clear. Label workflows something like Weekly Reminder – Send & Disable and Weekly Reminder – Re-Enable so the purpose is obvious to anyone reviewing them.
- Test with a small batch of contacts first to make sure the toggle and re-enrollment logic behave the way you expect.
- Monitor engagement. Weekly sends can quickly become too much for some audiences, so watch unsubscribe and bounce rates closely.
In a nutshell
Looping workflows aren’t officially supported as a one-click feature in HubSpot, but with a controlled two-workflow setup, you can safely send recurring reminders.
Just treat this as a power-user workaround: document it clearly, monitor it often, and keep your re-enrollment conditions tight.
Done right, it keeps your recurring campaigns running smoothly without introducing chaos into your automation system.
Not sure how to put HubSpot workflows to work? These 9 examples show exactly how to use them to save time and drive results.
Most workflow mistakes don’t show up until months later.
At RevBlack, we help companies design automation that scales cleanly across HubSpot and Salesforce.
If you want an extra set of eyes on your workflows before you roll them out, book a scoping session with our team and save yourself the cleanup later.
