This site is so confusing and lacks basic info. Any help or assistance is painful at best and nonexistent at worst. Where is the shipping information? All i see is woot says they are not responsible once they hand the package tonthe shipper. Well, if im responsible for shipping then shouldn’t i have control of the shipping? Shouldn’t we at least be informed of what shipper, how shipped, if signature is required, etc??? This site seems lime a scam to me, reviews are pitiful on all rating site’s. The deals are good. But with such lack of info if its to good to be true, it isnt. I emailed support but they wouldn’t even provide any ship info. What a joke is site is.
If you have Amazon Prime, shipping is free. If you don’t, then there’s a flat rate of $6 per order. That $6 can ship something small or something very large like a mattress, so Woot uses whatever shipping method is most economical to them and is decided by a computer, I think, which is probably how most online retailers do it.
If they were to do a tailored shipping like you request, they would have to charge a lot more money. I don’t know of any retailer that does it the way you suggest, not even Amazon.
There is a pretty extensive FAQ on Woot’s site which probably answers several of your questions.
I have been a customer of Woot’s since 2007 and have 549 orders from them. I can safely say this site is not a scam. A peek at my account page to verify that:

(Please note: I don’t work for Woot, I just volunteer to help out here on the forums.)
OMG we’re a scam?
In addition to @peaceetc’s nice answer…
A lot of our stuff ships from amazon and they decide how it ships. Could be UPS, Amazon delivery, or USPS.
Orders shipping from our vendors is usually UPS but it could be USPS or another delivery partner.
In addition to being a scam, we have a really nice community.
I have been a shopper since the website only days, no app, and never had a problem. I’ve never looked at the number of item’s I’ve purchased because the amount I have saved over the years and the fun community are more important to me.
I actually just used customer service and had THE BEST customer service experience of my life. I went to my orders because there were some I needed to return and some I didn’t receive. I didn’t find a solution so I clicked I need help. I opted for a phone call versus email and entered my number. Getting a call back from Woot and hearing the pre-recorded message was hilarious
. It built up anticipation of what to expect when a live person spoke. The customer service representative went above and beyond to help me with what I needed and answered some general questions as well.
You may want to try the call option to save time and frustration. My anxiety went from a 10 to ready to relax the rest of the day knowing Woot took care of everything for me.
I ordered a portable AC/Heater from Woot. It was sent quickly but when it was supposed to be delivered, I guess the UPS guy dropped it and destroyed the AC/Heater, so I never received it nor got an email updating me or anything, just crickets until I tracked down the package and found out what happened. By then, it was on its way back to the sender. I sent an email to Woot about the situation, no reply for three days, business days, and now I have been on hold for over an hour. Woot refused delivery of the busted up AC/heater, so I don’t know if that means I have to fight UPS for a refund, have a busted unit coming back to my house, or anything. Nothing was done proactively or even care to respond. I will never buy from Woot again, no customer service, not a care to fix when it went wrong, just nothing, absolutely nothing, oh, except being on hold for over 2 hours listening to the same busted piano song. Woot, get it together. This is a fail on all fronts from you.
Hi there. I’m sorry for the problems. I’ll check in with CS tomorrow morning.