How it starts: When Sarah Chen books Morpheus for Saturday 1 August 2026 and the charter is more than 50 days away, she only pays 50% upfront — a $1,100.00 deposit. The remaining $1,100.00 is collected automatically 51 days before the charter. If the charge fails, the system tries twice more and sends reminder emails along the way. If she still has not paid by 40 days before the charter, the booking is automatically cancelled and she receives half her deposit back.
Quick reference
Day
What happens
Who gets an email
Cron job
−51
System tries to charge Sarah's saved card for $1,100.00
Customer — collected or failed
Operator — only if failed
Admin — only if failed
balance-charge · 9am
−50
First reminder email if balance still unpaid (whether charge failed or was never attempted)
Customer only
reminders · 8am
−47
First retry — system tries to charge the card again
Customer — collected or failed
Operator — only if failed
Admin — only if failed
balance-charge · 9am
−45
Second reminder email if balance still unpaid
Customer only
reminders · 8am
−41
Final retry — last automatic charge attempt. Customer told this is the last try.
Customer — collected or failed
Operator — only if failed
Admin — only if failed
balance-charge · 9am
−40
Auto-cancellation if balance still unpaid. 50% of deposit ($550.00) refunded. Booking cancelled.
Customer — cancelled + refund
Operator — cancelled notice
Admin — full record
Providers — payout notice
reminders · 8am
Anytime
Customer pays balance manually from their booking page — stops all future chasing immediately
Customer — receipt
Operator — notification
Customer-triggered
Detailed flow
Recipients
Customer
Operator
Admin
Platform providers
−51
Day −51
51 days before charter — first automatic charge attempt at 9am
balance-charge cron
When it fires: booking is confirmed, balance is still outstanding, no previous charge attempt has failed, Sarah has a saved card on her account, and the charter is exactly 51 days away.
First automatic charge — $1,100.00 charged to Sarah's saved Visa ending 4242
Always fires
Two outcomes
Card charged successfully
Payment succeeded on first attempt
Booking marked as fully paid. No further emails or automatic actions will be taken on this booking.
Customer
Balance payment collected — CHR-4KW29B
Tells Sarah that $1,100.00 has been collected for Morpheus. Shows booking reference. No action needed.
Card declined
Stripe declined — insufficient funds, expired card, or bank block
Booking flagged as charge failed. System will try again automatically at Day −47 and Day −41.
Operator
Balance payment failed — CHR-4KW29B
Tells Sydney Harbour Charters that the $1,100.00 balance could not be collected from Sarah Chen. States the system will retry automatically and Sarah has been notified and can pay from her booking page at any time.
Admin
[Balance failed] CHR-4KW29B — Day −51
Full record: booking ref, boat, customer name and email, balance amount ($1,100.00), and the Stripe error message. States retries will fire at Day −47 and Day −41.
Customer
Action required: Balance payment failed — CHR-4KW29B
Tells Sarah the $1,100.00 balance could not be collected. States the system will try again automatically. Tells her she can also pay at any time from her booking page. Warns the booking will be automatically cancelled 40 days before the charter if the balance is not settled. Includes a Pay balance now button.
−50
Day −50
50 days before charter — first reminder email at 8am
reminders cron
When it fires: booking is confirmed, balance is still outstanding, and the charter is exactly 50 days away. This fires regardless of whether the Day −51 charge was attempted — it catches any booking that still has money owing.
First balance reminder — Sarah still has $1,100.00 outstanding, due in 10 days
Always fires
Customer
Reminder: Balance due in 10 days — CHR-4KW29B
Tells Sarah that $1,100.00 is still outstanding for Morpheus on Saturday 1 August 2026. Shows the deadline (Saturday 22 July 2026 — 40 days before charter). Warns that if payment is not received the booking will be automatically cancelled and only $550.00 (50% of the deposit) will be refunded. Includes a Pay balance now button linking to her booking page.
−47
Day −47
47 days before charter — first retry charge attempt at 9am
balance-charge cron
When it fires: booking is confirmed, balance is still outstanding, the previous charge attempt failed, and the charter is exactly 47 days away. Only runs for bookings where the Day −51 charge did not go through.
First retry — system tries to charge Sarah's card again for $1,100.00
Always fires
Two outcomes
Card charged successfully
Retry succeeded — card now works
Booking marked as fully paid. No further emails or automatic actions will be taken on this booking.
Customer
Balance payment collected — CHR-4KW29B
Tells Sarah that $1,100.00 has been collected for Morpheus on Saturday 1 August 2026. Confirms she is all set. Shows booking reference.
Card declined again
Second failure — one more retry at Day −41
Customer
Action required: Balance payment failed — CHR-4KW29B
Tells Sarah the $1,100.00 balance still could not be collected. States the system will try once more automatically. Tells her she can pay from her booking page at any time. Includes a Pay balance now button.
Operator
Balance payment still outstanding — CHR-4KW29B
Tells Sydney Harbour Charters the $1,100.00 balance from Sarah Chen could not be collected. States one more automatic retry will follow.
Admin
[Balance failed] CHR-4KW29B — Day −47
Full record with Stripe error. States next retry is Day −41.
−45
Day −45
45 days before charter — second reminder email at 8am
reminders cron
When it fires: booking is confirmed, balance is still outstanding, and the charter is exactly 45 days away. This is a reminder email only — no charge attempt. If Sarah already paid manually or a charge succeeded at any point, this email will not send.
Second and final reminder — Sarah has 5 days left to pay before automatic cancellation
Always fires
Customer
Action required: Balance due in 5 days — CHR-4KW29B
Tells Sarah that $1,100.00 is still outstanding and the deadline is Saturday 22 July 2026 — 5 days away. Warns the booking will be automatically cancelled and only $550.00 refunded if payment is not received. Includes a Pay balance now button linking to her booking page.
−41
Day −41
41 days before charter — final retry charge attempt at 9am
balance-charge cron
This is the last automatic charge attempt. If this fails, the system makes no further attempts. The booking will be cancelled the following day at Day −40 if the balance remains unpaid.
Final retry — last automatic charge of $1,100.00. No further attempts after this.
Always fires
Two outcomes
Card charged successfully
Final retry succeeded
Booking marked as fully paid. The Day −40 auto-cancellation will not fire. No further emails or automatic actions will be taken.
Customer
Balance payment collected — CHR-4KW29B
Tells Sarah the $1,100.00 balance has been collected for Morpheus on Saturday 1 August 2026. Confirms she is all set. Booking proceeds as normal.
Card declined — final failure
All three automatic attempts exhausted. Booking will be cancelled tomorrow at Day −40.
Customer
Final notice: Balance payment failed — CHR-4KW29B
Tells Sarah this was the final automatic attempt. States clearly that the booking will be automatically cancelled 40 days before the charter if the balance is not settled. Tells her she can still pay from her booking page at any time to prevent cancellation. Includes a Pay balance now button.
Operator
Balance payment still outstanding — CHR-4KW29B
Tells Sydney Harbour Charters this was the final automatic attempt. States the booking will be cancelled if Sarah does not pay 40 days before the charter.
Admin
[Balance failed] CHR-4KW29B — Day −41 FINAL
Full record with Stripe error. States no further automatic attempts will be made. Booking will be cancelled at Day −40 if unpaid.
−40
Day −40
40 days before charter — auto-cancellation at 8am
reminders cron
When it fires: booking is confirmed, balance is still outstanding, a deposit was collected, and the charter is exactly 40 days away. If Sarah paid manually at any point, or any of the three charge attempts succeeded, this does not fire. It only runs for bookings that are genuinely still unpaid after all attempts.
Auto-cancellation — Sarah never paid the $1,100.00 balance. Booking cancelled, partial refund issued.
Always fires
Stripe refund
$550.00 (50% of the $1,100.00 deposit) is automatically refunded to Sarah's card. If the Stripe refund fails, it will shows refund_pending on the booking so admin can process it manually. The cancellation proceeds either way.
Database update
Booking status set to cancelled. Reason recorded as "Balance not settled within 40 days of charter". Refund amount and outcome saved to the booking record. If the Stripe refund fails, the booking is flagged so admin can process it manually.
Emails sent
Customer
Booking cancelled — balance not received — CHR-4KW29B
Tells Sarah the charter on Saturday 1 August 2026 has been automatically cancelled because the remaining balance was not received 40 days before the charter. Shows refund summary: $1,100.00 deposit paid, $550.00 refunded to card, $550.00 retained by the platform. If the automatic refund failed, tells her the team will process it manually within 2 business days.
Operator
Booking auto-cancelled (unpaid balance) — CHR-4KW29B
Tells Sydney Harbour Charters that CHR-4KW29B for Morpheus on Saturday 1 August 2026 has been automatically cancelled because Sarah Chen did not pay the remaining balance 40 days before the charter. Confirms their 10% operator deposit is retained. The date slot is now available for new bookings.
Admin
[Auto-cancelled] Unpaid balance — CHR-4KW29B
Full cancellation record: booking ref, boat, customer name and email, charter date, deposit paid ($1,100.00), refund status (auto-refunded with Stripe ID, or FAILED — manual action required in red). If refund failed, refund_pending will be shown in the booking page.
Providers
Job cancelled — CHR-4KW29B — Morpheus
Sent to each platform provider booked on this charter (e.g. a photographer at $450.00). Shows: cancellation reason (customer did not pay 40 days before charter), their booked item value ($450.00), platform fee deducted (5% = $22.50), their 50% cancellation share ($213.75), and a 5–10 business day payout timeline. Asks them to remove the date from their schedule.
B
Security Bond
24–48 hours before charter — Pre-authorization hold
Security Process
Important: The security bond is a temporary hold, not a permanent charge. It
ensures funds are available for potential damages or incidental costs.
1. Automatic Capture
A $2,000 bond is automatically held on the customer's saved card 1–2
days before departure. The customer receives an email confirming the hold is successful.
2. Inspection & Release
After the charter, the operator inspects the boat. If no issues are reported, the hold
is released within 3–7 business days. Banks may take a few extra days to show this in the
balance.
Operator
Security bond status notification
The operator is notified if a bond fails to capture. If failed, the operator should
ensure a new card is provided before the customer boards.
Any
Anytime
Customer pays balance manually from their booking page — stops all future automated actions
Customer-triggered
How it works: Sarah logs into her booking page at any point before Day −40. She sees her outstanding balance of $1,100.00 and a Pay balance now button. The charge runs immediately against her saved card. If her card is declined or she has no card saved, she can enter new card details inline. Once paid, the booking is immediately marked as fully paid — no further emails or automatic actions will be taken.
Sarah pays $1,100.00 manually via her booking page — payment confirmed immediately
Customer-initiated
Booking marked as fully paid immediately. The Day −40 auto-cancellation will not fire. No further reminder emails or charge attempts will be made.
Customer
Balance payment received — CHR-4KW29B
Tells Sarah that $1,100.00 has been received for Morpheus on Saturday 1 August 2026. Confirms she is fully paid and all set for her charter. Shows booking reference.
Operator
Balance received — CHR-4KW29B
Tells Sydney Harbour Charters that the $1,100.00 balance for CHR-4KW29B (Morpheus, Saturday 1 August 2026) has been paid by Sarah Chen. Full payment is now complete.