For example if I have 4 martini glasses can I use calculated shipping and if a customer buys one, it is the amount in the shipping calculator. If they buy 3 can I add a rule that will charge $5 for each additional? Or even better a percentage? If so, is it possible to then charge a different amount if the items are small and will only cost an additional $2.00 per item? At the moment I am only selling in Canada and have Canada Post and UPS as options.

Yes the calculations for combined shipping happen on the cart. eBay is a bit unusual, most sites don't show ANY shipping information until you go to checkout.

Can I use calculated shipping and have different amounts added for additional glasses same listing? | Selling

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Can I use calculated shipping and have different amounts added for additional glasses same listing? | Selling | eBay Canada EN