An Orthodox Jew is in the business of selling gift and food baskets online. Though the bulk of his business is with Jews, he does have non-Jewish customers who buy his products for their own enjoyment.
A non-Jewish customer orders chametz cookies. The seller will ship them out before Pesach via UPS. But the goods will be en route on Pesach.
The buyer has a range of options as to who will be the shipper: he can choose US Mail, or UPS Land, or UPS Overnight.
If sent by UPS, the shipment is insured.
Do we have a problem here? Does it belong to him once he ships it? Does the seller have the right to call UPS and tell them to not deliver it and that he wants the merchandise back? Even if title passes to the buyer when you ship it, what if the risk of loss is the seller's until actual delivery; does this achrayus make it his le'halacha? Perhaps the fact that UPS would have to pay him if they lost it means that it is his, although he would have to use the proceeds to refund the buyer? And if the achrayus of "risk of loss" makes it his, perhaps this is a form of ownership that is not amenable to hefker? Can he be mafkir/mevateil the en route chametz? The general sale of Chametz done by the local rabbis is not an option. You can't sell something you're shipping to someone else.
I recently saw that in the Grach al Hashas there's a letter from Reb Chaim about a very similar question. If I have time, I'll put it in here bl'n.
To pasken this shailah, you have to know Orach Chaim, Choshen Mishpat, and the Uniform Commercial Code. If you bring this question to the average Orthodox Rabbi (me), let's hope he has the elementary seichel to realize that he needs to pick up the phone and call an attorney who is knowledgeable in the UCC, and then bring all the facts to the higher echelon of poskim. (I did. I have a friend who is a professor at a law school who also has Yoreh Yadin, and I have access to a top level Poseik.) I'm not going to tell you what the poseik said, because 1. On Pesach, the discussion stimulated by a question is more valuable than any one answer, and 2. I'm not convinced that I understand why the poseik paskened as he did.
Many businesses sell their chametz before pesach. Selling their stock is an accepted method of avoiding the chametz problem. Some, such as grocery stores, food distributors, and whiskey distillers, sell merchandise worth a great deal.
My question is this: what does it say on their insurance policy? Who would be paid if there was a fire that destroyed the merchandise on Pesach? Would the insurance company pay the goy to whom the chametz was sold? Of course not. Maybe the money would go to the goy and then to the Jew. But once the Jew sells his chametz, does he have an insurable interest in the Chametz? (That's a rhetorical question. You can't insure something that's not yours.) So, if the insurance policy says it belongs to the Jew, and in event of a loss the money would be paid to the Jew, who really owns it?
Having the business owner come to my house erev Pesach, and his telling me that he would do whatever was necessary, was a great experience. Canceling the order would have cost him a customer and hurt his reputation, and he was determined to do the right thing according to how I would pasken. It would have been easy for him to rationalize that it's muttar, but he was unwilling to do that. I think he is a mussar haskel about how an Ehrliche Yid ought to do business.
This is his website, in case you're looking for a reliable source for gift baskets from an ehrliche Yid: Kosherbyte.
Passing of Title
Risk of Loss
דבר הגורם לממון
דינא דמלכותא דינא