Allow Customers to Make Repeat / Recurring Bookings (Customer Portal)

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Allow Customers to Make Repeat / Recurring Bookings

Customer Portal Recurring Booking

OctopusPro lets customers schedule repeat (one-off) or recurring (ongoing) appointments directly from your Customer Portal. This helps you secure repeat work, reduce back-and-forth scheduling, and build a more predictable pipeline—while customers can lock in their preferred days and times in one booking flow.

Key benefits

  • More repeat business: Customers can book multiple visits in one checkout flow.
  • Less admin work: Fewer calls/messages to schedule follow-up appointments.
  • More predictable workload: Future appointments appear on your calendar.
  • Flexible invoicing: Choose when invoices are created for future visits.

Table of contents

  1. How repeat/recurring bookings work
  2. Enable “Allow customers to make repeat/recurring bookings”
  3. Choose when invoices are created
  4. Customer experience when the feature is disabled
  5. Repeat a booking once
  6. Create multiple recurring bookings
  7. Review and edit the scheduled dates
  8. How recurring bookings appear in the Admin Portal
  9. Best practices & common tips

How repeat/recurring bookings work

When a customer schedules a recurring series, OctopusPro creates multiple bookings (one per occurrence). This makes it easier to:

  • Manage each visit independently (status updates, reschedules, notes, attachments).
  • Invoice and track payments per visit (depending on your invoice settings).

Enable “Allow customers to make repeat/recurring bookings”

  1. Go to Settings → Customer Portal → Flags & Permissions.
  2. Find the Booking Flags section.
  3. Enable Allow customers to make repeat/recurring bookings.

Once enabled, customers will see repeat/recurring options while scheduling on the Customer Portal.

Choose when invoices are created

When you enable this feature, you’ll also choose when invoices should be generated for the bookings created.

Option A — Create invoices for all bookings (including future ones)

  • Invoices are generated for every occurrence immediately (including future appointments).
  • Best when you want invoices ready upfront for forecasting or scheduled payments.

Option B — Invoice the first booking only, then invoice each occurrence

  • Creates an invoice for the first appointment right away.
  • Each future booking generates its invoice per occurrence (as each booking is created/processed).
  • Best when you don’t want a large batch of future invoices created upfront.

Option C — Create invoices manually

  • Bookings are created, but invoices are generated only when you manually create them.
  • Best when you prefer to confirm resources/availability before invoicing, or if pricing may vary visit-to-visit.

Tip: Choose the option that matches your billing workflow (upfront billing vs pay-per-visit vs manual approval).

Customer experience when the feature is disabled

If Allow customers to make repeat/recurring bookings is disabled, customers can only schedule one appointment by selecting a date and time. Repeat/recurring scheduling options won’t appear in the Customer Portal.

Repeat a booking once

When the feature is enabled, customers can choose between:

  • Book once
  • Repeat once
  • Multiple repeats (recurring series)

If they select Repeat once:

  1. Select the first appointment date and time.
  2. Select the repeat date (the same time is typically applied).
  3. Confirm and submit the booking.

This is ideal for quick follow-up visits (e.g., “same time next week”).

Create multiple recurring bookings

If customers select Multiple repeats, they can schedule a series of future appointments in one flow.

  1. Select the first booking date.
  2. Choose when the recurrence should stop:
    • by selecting an end date, or
    • by choosing a set number of occurrences.
  3. Set the recurrence frequency:
    • Enter a number (e.g., every 3) and choose a unit (e.g., days or weeks).
    • Example: “Every 3 weeks” or “Every 5 days”.
  4. If you choose a weekly-style option (e.g., weekly/biweekly), select the preferred days of the week.
  5. Select the preferred time.
    • The selected time is applied to the current and upcoming appointments unless edited later.

Example

To book starting tomorrow, repeating 5 times, every 3 weeks, on Wednesday/Thursday/Friday at 10:00 AM:

  • Start date: tomorrow
  • Occurrences: 5
  • Frequency: every 3 weeks
  • Days: Wed / Thu / Fri
  • Time: 10:00 AM

Review and edit the scheduled dates

After clicking Next, the Customer Portal displays a list of scheduled dates so the customer can confirm everything before submitting.

If available, customers can click Edit to adjust individual occurrences (for example, changing one specific date/time without changing the entire series).

How recurring bookings appear in the Admin Portal

In the Admin Portal, each occurrence is created as its own booking. This helps you manage each visit independently (status, notes, reschedules, assignments, etc.).

Invoices are created based on the invoice option you selected (all at once, first + per occurrence, or manual).

Best practices & common tips

  • Set clear rescheduling/cancellation policies so customers understand how recurring visits are handled.
  • Keep availability accurate (fieldworker working hours and calendar blocks) to reduce failed booking attempts.
  • If pricing can change over time, consider manual invoicing or invoice per occurrence to avoid editing future invoices.
  • If customers need exceptions (skip a week, move one visit), direct them to the Edit option (if available) or ask them to contact you.

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