This is actually a very enjoyable thread if purchase contract law interests you. You have a contract if there is offer to sell, acceptance, and consideration(payment.) Cigarbid entered into a contract with Smithbw when they accepted his consideration(payment) for the initial box of cigars. CBid's legal responsibility to make Smithbw whole in a reasonable time frame on the contract issue did not end when the cigars left CBid for the common carrier. That he was charged for the second box of cigars, even though he didn't receive the first box, borders on being an illegal charge. Because he didn't receive the alleged first box, defacto, the second box is the one he legally paid for. Smithbw's credit carrier would have most assuredly charged back the "first" box to CBid, because Smithbw never received it. CBid placed the onus of the lost property on Smithbw, which in most commercial transactions is not only illegal, but an extremely poor public relations practice.
When the second box was sent to Smithbw, he was charged the auction winning price for the initial box. Two things happened at that time. CBid consented to selling the second box at the auction winning price thereby nullifying the exclusivity of the auction price. The claim that smithbw only "won" one box is moot. CBid made an offer to sell the second box at the auction price, smithbw accepted, and he was charged. Offer, acceptance, consideration=contract.
Two boxes were ultimately offered to smithbw at the auction price, he accepted, and was charged. For CBid not to make him whole on both boxes is a clear violation of the sales contract. CBid now has the responsibility of replacing the damaged cigars and securing financial damages from the carrier, but smithbw has no legal standing in the transaction between CBid and the carrier. His remedy is to receive both boxes of cigars for which he paid, in the condition for which he paid for them.
Isn't this fun?
In reality...I've been buying cigars for forty years, and for many years, pre-internet, by catalog. I've never had any vendor double charge me on a lost shipment. It just isn't done.