Create a recurring product, attach it to a client as a subscription, and let invoices generate automatically each cycle
For retainer work or recurring services, subscriptions automate the monthly (or quarterly, or annual) invoice generation so you don’t have to remember to bill each cycle. This guide walks through setting up your first recurring subscription end-to-end.
A monthly retainer subscription: $3,000/month, auto-billed on the 1st of each month, with the client’s saved card auto-charged. If the charge fails, dunning emails go out automatically.
For the auto-charge to work, the client needs a saved payment method.
They pay the first invoice manually
Send a 'set up payment method' link
Manual entry (don't do this)
Recommended. The first invoice generates and emails a portal link. They pay using a card and check “Save this card for future payments.” Subsequent invoices auto-charge that card.
From the subscription’s actions menu, click Request Payment Method. The client gets an email with a secure link to add a card without paying anything yet. The card saves for future auto-charges.
Don’t take card numbers over phone or email and enter them manually — it explodes your PCI scope. Always use the portal flow.
Personal follow-up at day 7 (when it goes past_due) recovers the most subscriptions. The client usually wants to keep the service — they just have a card issue. A quick email or call from a real person fixes it faster than another automated email.
If the client wants to upgrade, downgrade, or swap to a different plan:
Upgrade now (with proration)
Downgrade at next renewal (no proration)
Same-day swap (no proration)
From the subscription’s actions menu, click Change Plan. Pick the new product. The current cycle prorates — credit for unused old plan, charge for prorated new plan. Next cycle bills the full new plan price.
Same flow but pick At next renewal. Current cycle finishes at old price; next cycle starts at new price.
For renames or non-pricing swaps. No credit or charge; the cycle continues at the old price; next cycle uses the new product.
Check the next-billing-date — it may not have arrived yet. Check the activity log for any errors. Verify the payment processor connection is healthy.
Auto-charge not running on the cycle date
The client may not have a saved payment method. Send them a payment-method link from the subscription’s actions menu. Until they save a method, each cycle’s invoice generates but waits for manual payment.
Proration math doesn't match what I expected
Proration depends on the change type. Upgrades prorate (credit + charge); downgrades-at-renewal don’t. Same-day swaps don’t. Double-check which option you picked. The activity log shows the math.
Failed payment retry isn't running
Check the dunning policy in Payment Settings. Also verify the processor connection is authorized — Stripe OAuth tokens can expire and a disconnected processor can’t retry.
Pre-charge reminder didn't send
Pre-charge reminders use your transactional email infrastructure. Check that your sending domain is verified — see Email Domains. Also confirm reminders are enabled for this subscription.