LetterAgent

Mail physical letters by just asking your AI assistant.


Status: LetterAgent is currently in private testing ahead of public launch. Everything on this page describes the service as it works today.

Home > Guides > Shipping a giveaway prize

How do I ship a package for a giveaway prize?

Confirm the winner's full mailing address in writing, pack the prize as if it were a paid order, and send it with tracking you share with the winner. A giveaway prize is still a parcel, so the same packing, labelling, and proof-of-delivery habits apply, plus one extra step: keep the winner's consent on file.

How do I confirm the winner's address without awkwardness?

Ask for the address in the same message where you announce the win, and ask for it in full: name, street address or PO box, apartment or unit number, city, province or state, and postal or ZIP code. A social media handle is not a mailing address, and a partial address from an old profile can send the prize to a former home. Ask the winner to read the address back to you, or to paste it exactly as it appears on their own mail, and save that message.

Set a reply window when you announce the win, such as a week to claim the prize, and say what happens if no address arrives: a redraw, or the prize going to the next name drawn. That deadline protects you from a prize sitting boxed for months, and it is fairer to runners-up than an open-ended wait. If the winner is a minor, get a parent or guardian's address and consent instead, and do not ask a child for a home address directly.

StepWhat to doWhy it matters for a giveaway
AnnounceName the winner publicly only with their permissionSome winners want privacy, and a surprise tag can backfire
ConfirmGet the full address in writing, read backPrevents misdelivery and disputes about where it went
PackPack like a paid order, with a gift note insideThe unboxing is part of the prize experience
SendUse tracking, and share the number with the winnerTracking ends most "where is it" messages before they start
CloseAsk for delivery confirmation, and thank themA confirmed delivery closes the giveaway cleanly

How should I pack a prize?

Pack it the way you would pack something you sold. Fragile prizes get wrap and fill, liquids get a sealed bag inside the box, and anything with a battery follows the carrier's battery rules. A short handwritten note inside the box ("Congrats, and thanks for entering") costs nothing and turns a plain parcel into a prize. Do not include a sales flyer or a discount pitch unless the giveaway terms said one would be included; a winner who opened a gift does not want to feel upsold.

Photograph the packed prize before you seal the box, and photograph the label once it is on. If the parcel arrives damaged or the winner says the box was empty, those two photos are your evidence for a claim, and they also prove what you actually sent. Keep the receipt and the tracking number until the winner confirms delivery, not just until you drop the parcel off.

Who pays for shipping, and what about cross-border prizes?

State who pays shipping in the giveaway terms, before anyone enters. The usual setup is that the host pays shipping, and a winner who discovers a shipping bill at delivery will rightly feel misled. If the prize can only ship within one country, say so in the terms too, since a winner abroad who cannot receive the prize creates a dispute you could have avoided with one line.

Cross-border prizes add duties and customs forms. A prize sent as a gift still crosses the border as a parcel, and the recipient may face duties or a brokerage charge on arrival, depending on the item and the destination. Check the carrier's rules for the item before promising international shipping, and tell the winner in advance if any charge could land on their side. When the prize is high value, insurance is worth it even though the winner paid nothing: replacing a lost prize costs you twice, once in goodwill and once in cash.

Can I use a LetterAgent label for a giveaway prize?

For a prize shipped within Canada, yes, within the usual limits: LetterAgent labels are Canada-only, flat-rate Canada Post Xpresspost, with a 5 kg maximum. The flow is a per-label quote, your approval of the exact price, a one-time Stripe payment, and a label PDF you print and attach. Xpresspost tracking lets you share a tracking number with the winner. For a prize going outside Canada, LetterAgent labels do not apply, and you will need a carrier that serves that destination.

Related guides

Ready to ship it? Get a shipping label with LetterAgent: describe it to your AI assistant, approve the exact quoted price, and get your label.


LetterAgent is a working name. Prices include print, postage, and our service fee. US prices in USD, Canadian prices in CAD (Canadian prices exclude applicable sales tax, added at checkout). Currently in private testing.

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