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?
While HubSpot previously required workarounds for loops, Professional and Enterprise tiers now feature native Scheduled Workflows for recurring tasks.
A record can move through a workflow multiple times via re-enrollment, a Recurring Schedule trigger, or by being enrolled via another workflow
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. While you can use a Scheduled Trigger for simplicity, a two-workflow 'toggle' setup is still useful for complex, behavior-based loops.
- 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
Note: If you are on a Professional or Enterprise plan, you can skip these steps by using the native 'Scheduled' trigger type.
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 brief delay (e.g., 15 minutes), then 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.
Expert Note for Salesforce Users
If your HubSpot portal is integrated with Salesforce, keep your "Weekly Email Flag" as a HubSpot-only property.
- Why? Looping property changes can trigger unnecessary syncs between systems. If this property is mapped to Salesforce, every "flip" of the switch consumes API calls and can inadvertently trigger Salesforce Flows or Apex triggers, leading to potential "sync storms" or record locking.
- The Fix: When creating the property in HubSpot, ensure it is not mapped to a Salesforce field. Keep the "automation logic" contained within HubSpot to maintain a clean, high-performance integration.
Things to know about re-enrollment
HubSpot limits re-enrollment triggers and caps the number of times a record can be enrolled in a single workflow within 24 hours.
Property changes and form submissions generally qualify for re-enrollment, whereas engagement triggers like email clicks are excluded to prevent loops triggered by bot activity.
That’s why a dedicated property like Weekly Email Flag works well for this pattern.
A record cannot re-enter a workflow if it is still active in it, and HubSpot prevents re-enrollment for the same property value change within the same minute. 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:
- If using the workaround, use 'Delay until a day or time' actions to anchor the email to Friday morning.
- 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
While HubSpot now offers native Scheduled Triggers, complex or behavior-based loops still require a custom multi-workflow setup.
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.
