Overview
SquadTrip automatically charges travelers on their scheduled payment dates. If a scheduled payment fails -- due to a declined card or insufficient funds -- the system automatically retries the payment every 2 days, up to 3 times (up to 4 tries in all) — as long as the organizer has Retry Failed Payments enabled for the trip (it is on by default, but it can be switched off). If a card has expired or was lost or stolen, retrying will not help, so the traveler needs to add a new card. When SquadTrip can tell a card can't be charged again, it doesn't retry it, and the traveler's email says so. SquadTrip does not cancel the booking automatically, but a trip organizer can cancel a traveler whose payment stays unresolved. This article explains what happens, what both organizers and travelers should do, and how to resolve failed payments.
How Auto-Billing Works
Scheduled payments are set up when the organizer creates a payment plan (deposit + monthly installments)
SquadTrip runs a billing job that processes all due payments
A reminder email is sent to travelers before each scheduled payment
On the scheduled date, the traveler's card on file is charged automatically
If the charge succeeds, the payment is marked as complete
If the charge fails, the system retries every 2 days, up to 3 times (up to 4 tries in all), when the trip's Retry Failed Payments setting is on (it can only be on while Auto-Charge is on -- an organizer can switch auto-charge off for new bookings on a trip, in which case those travelers pay each installment themselves; travelers who already booked stay on auto-charge unless the organizer stops it for them on their Traveler Details page)
What Happens When a Payment Fails
Step | What Happens |
Day 0 | Scheduled payment fails (card declined, insufficient funds, etc.) |
Day 0 | Payment is marked as "Failed" in the system with the specific error |
Day 2 | System automatically retries the payment |
If retry fails | Another retry is scheduled 2 days later |
Retries continue | The system retries every 2 days, up to 3 times. After the 4th failed attempt (the original charge plus 3 retries) the payment is marked failed and is not retried again. |
SquadTrip does not cancel the booking automatically when a payment fails — the traveler stays on the trip with an outstanding balance. Cancelling is the organizer's decision, and an organizer can remove a traveler whose balance stays unpaid. A traveler who cannot pay should contact their organizer directly.
For Travelers: What to Do
If you receive a notification that your payment failed:
Check your card -- Make sure the card on file hasn't expired and has sufficient funds
Update your payment method -- Click Update Card (or Add a New Card) in the failed-payment email, or log in to your traveler dashboard, and update your card information if needed
Wait for the automatic retry -- The failed-payment email tells you whether your card will be retried and on what date. If it says the payment won't be retried, pay manually or update your card
Or pay manually -- You can pay at any time from your trip's Payments section in the traveler dashboard -- Retry Payment on the failed row, Pay Now on a scheduled row, or Make New Payment
Common reasons payments fail:
Card expired
Insufficient funds
Bank blocked the transaction (call your bank to authorize)
Card was replaced with a new number
For Organizers: What to Do
If you notice a traveler's payment didn't process:
Open the trip and find the traveler -- View the traveler's payment history in your dashboard. A payment that didn't go through shows as "Failed", then "Overdue" under its retry date while an automatic retry is pending; it stays one row and turns "Paid" once a retry goes through (the decline reason is not shown there -- the traveler's failed-payment email carries it).
Contact the traveler -- Let them know their payment didn't go through and ask them to update their card if needed. The traveler is emailed once when a payment fails, not again after each retry. If you're thinking of cancelling their booking, you can first send them a last-chance pay link from the cancel options: choose Send a last-chance pay link instead, and their booking stays active (see How to Cancel a Trip With or Without a Refund).
Wait for auto-retry -- The system retries every 2 days automatically.
Manually reschedule -- If needed, you can use Edit Order to adjust the traveler's payment dates or redistribute their remaining balance.
Checking Payment Status
Organizers:
Open the trip, find the traveler and open their account details
Payment logs show each scheduled payment with its status: Scheduled, Paid, Failed, Unpaid, Overdue or Auto-charge OFF
The decline reason is not shown in the log -- the traveler receives it in their failed-payment email
Travelers:
Log in to your traveler dashboard
View your payment schedule showing upcoming and past payments
Contact the organizer if you have questions about your balance
Important Notes
Auto-billing is ON by default for all payment plans
Failed payments are retried automatically every 2 days, up to 3 times (up to 4 tries in all) — but only if Retry Failed Payments is enabled for that trip
The traveler's booking remains active even when payments fail -- they are not removed from the trip
Reminder emails are sent before each scheduled payment date
If a traveler's card is repeatedly declining, ask them to update their payment method or contact their bank
Small rounding balances (anything up to $0.10) from installment math are cleared automatically once a day -- no action needed
Troubleshooting
Problem | Solution |
Payments didn't run at the scheduled time | Auto-billing processes payments in batches. If your payments are slightly delayed (by hours), this is normal. If they're more than a day late, contact [email protected]. |
Traveler was charged twice in one month | This can happen if a failed payment was retried close to the next scheduled payment date. Check the payment logs -- one may be a retry of a previously failed payment. |
Traveler shows $0.01 remaining balance | This is a rounding artifact from dividing installments evenly. Any remaining balance up to $0.10 clears automatically within 24 hours. No action is needed. |
All payments failing for multiple travelers | Check your Stripe or Square account status. If your payment gateway has an issue (restricted account, expired credentials), all charges will fail. |
Frequently Asked Questions
Q: Will my booking be canceled if a payment fails? A: Not automatically — but it can be. SquadTrip retries the payment in 2 days and your booking stays active in the meantime, so nothing is cancelled by the system. Cancelling is your trip organizer's decision, and they can cancel a reservation whose balance stays unpaid. Update your payment method and pay as soon as you can — and if you are not able to, contact your organizer directly to work it out.
Q: How many times does the system retry a failed payment? A: The system retries every 2 days, up to 3 times (up to 4 tries in all). After the 4th failed attempt the payment is marked failed and is not retried automatically — it has to be resolved manually. If your card keeps failing, update your payment method to avoid repeated declines.
Q: Does the traveler get notified when a payment fails? A: Yes. SquadTrip emails the traveler automatically when a payment fails: once for that payment, not again after each retry. The email says whether and when the card will be retried, and its buttons open the traveler's booking to pay or update their card. Your trip's email settings add your own message at the top of that email; they don't control whether it is sent. It is still worth contacting the traveler directly, since a failed-payment email can be missed.
Q: What should I do if payments didn't process overnight as expected? A: Wait a few hours -- auto-billing processes payments in batches and may run at different times. If payments haven't processed after 24 hours, check your Stripe/Square account status for any issues, then contact [email protected] if the problem persists.
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Contact: [email protected]