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I want to order a new laptop to be delivered to my airbnb in Japan. Basically the same as if I were carrying it with me in the airport, and leaving a month later (in which case customs need not apply) --- only seemingly more tricky.

Do customs apply when the product is sent in, rather than carried in?

What can I expect? Will it arrive to my residence, or will I have go clear it at local customs?

When you enter japan by air, you’ll be asked to fill out a customs declaration. Fill it out in duplicate and check the box where it says “unaccompanied items.”

On the reverse side where there’s an itemization, it’s helpful to be as detailed as possible, for example including the laptop serial number.

You’ll get to keep one of the copies of your declaration form stamped by the customs officer.

When sending the laptop be sure to declare its value but write in big letters “UNACCOMPANIED BAGGAGE.” Having the serial number on the customs declaration on the package is useful too. Assuming you sent it to your home or hotel, it’ll arrive there. A postal official might want to see your customs declaration. Sometimes, they’ll want you to pick it up at the local post office so they can get the form.

Keep copies of everything just in case returning to your home country you encounter an overzealous customs agent who wants to duty your laptop coming back.

More info here: http://www.customs.go.jp/english/c-answer_e/keitaibetsuso/7102_e.htm

As to your first question: this will be much easier to accomplish if you carry the laptop with you into Japan. That way, there'll be no question that it's your property, acquired before entering Japan, and that because you're going to be present only temporarily in Japan, no Customs duty should be assessed.

・Source: A page in English from the Japanese customs authority

If the computer arrives separately from you, the box must be specifically labeled so as to "connect" to you, and you must declare the contents when you yourself enter Japan. These requirements are set forth in the Japanese Customs page linked above under "Unaccompanied baggage."

The page linked above says that upon your own entry and declaration about unaccompanied baggage, you receive a "clearance" document which allows importation of this property without duty. It's unclear what happens to such package if it arrives before you do. I also wonder how you could complete the declaration during your own entry if the computer is new, hadn't been in your hands, and presumably you wouldn't have or be able to disclose its serial number.

As to your second question: I have no idea, never having done this.