A Stripe payout is in the books once, whichever comes in first: Stripe’s record or the bank file
On Reconcile → Stripe, a payout Stripe sent that the books don’t have now has Record This Payout — and Record All, when there are several. Each goes in as a transfer from Stripe to the account Stripe pays out to, dated the day it reached the bank, and pressing it again adds nothing. When the bank file comes in, the review says the deposit is already recorded, and importing ticks that transfer off on the statement instead of adding the money a second time. A deposit days from a payout the statement has already ticked off is never taken for it: the review names that payout and starts the row unticked, and checked, it comes in as a payout of its own. Import the bank file first instead, and a deposit that is one of Stripe’s payouts comes in as a transfer from Stripe, so Reconcile → Stripe finds it there and never offers to record it again. A deposit booked as income beside a payout the books already have, still waiting for its deposit, is listed as a likely duplicate, and its fix is Remove My Entry — Make It a Transfer would have taken the payout out of Stripe twice. Bookkeeping Settings has a Stripe card: choose the account Stripe pays out to, and see the day Stripe’s books start. And bringing a month in from Stripe on Reconcile → Stripe (Bring In September From Stripe) comes back to the check, saying what it brought in.