I assumed that the bidding would just take care of itself, that everytime I got outbid, the auto-snipe feature would bid for me AND snipe.


JBidwatcher does NOT do that, because that would be counter to the point of sniping. Sniping is placing a SINGLE bid, once, at the end of the auction, for the maximum amount you're willing to pay. It does NOT keep you as the 'high bidder' of the auction all the way until the end, because that's an explicitly bad position to be in. It's a battle of knowledge. Every bid you place on-site exposes some knowledge about you, and what you're willing to pay, and what you're interested in. Sniping minimizes that information leakage by not even showing that you're interested in an item until the last seconds of the auction.

Picture it this way, if you have a max of $50, an item is currently at $10, and you bid $11 to become the high bidder, and there's 3 days left, the other bidder can come back, bid $12, or $15, or $20. If, instead, you wait until there's 5 seconds left in the auction, and bid for $50, then by the time they get an 'outbid notice' in their email, the auction is already over, and you got it for $11, instead of going back and forth with other bidders.

Now, if they had bid $65 originally, but the next highest bid (or the minimum bid) was around $10, the amount they have to pay will suddenly jump from $10 to $51, and they'll win it. Sniping works best against people who try to lowball prices, in which case it's their own fault. Sniping also works best if you put in what you are really willing to pay for an item, so that if it goes over that number, you can walk away comfortable that you wouldn't have been willing to pay that much for it anyway.