Does an earn-out obligation transfer if I resell the business during the earn-out period?

Not automatically. An earn-out obligation is a personal contractual commitment the original buyer made to the original seller, and reselling the business during the earn-out period does not, by itself, shift that liability onto the new purchaser unless the original earn-out agreement expressly allows assignment or assumption of the obligation, and the new purchaser separately agrees to actually take it on as part of the resale.

Without that kind of express arrangement, the original buyer generally remains personally on the hook to the original seller for the earn-out even after parting with the business itself, which is a real risk worth thinking through before agreeing to sell during an active earn-out period. A seller worried about this scenario from the outset should negotiate protective language into the original earn-out agreement, such as requiring the buyer to obtain the seller's consent before reselling during the earn-out period, or requiring any successor purchaser to formally assume the earn-out obligations as a condition of that resale being permitted at all.