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.

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Can I ship multiple packages to the same address?

Yes, you can ship multiple packages to the same address, but each box needs its own label and tracking number. One label covers one parcel only, so mark each box clearly, keep a list of what is in each, and tell the recipient how many parcels to expect.

This question comes up whenever one order does not fit in one box: a furniture set in two cartons, a shop order split across sizes, a move sent in stages. The rule is simple, but breaking it causes real trouble. A single label pasted on two boxes means the carrier's system sees one parcel, and the second box travels with no identity at all.

Why does each box need its own label?

A shipping label is a contract for one parcel: one weight, one size, one tracking record. Sorting machines read the barcode and route that box. If two boxes share one label, the system may deliver one and flag the other as an unmatched item, or charge an adjustment when the weights do not match. In the worst case, the unlabelled box sits in a depot while staff try to work out where it belongs.

Some carriers offer a multi-piece shipment option for business accounts, where several boxes travel under one shipment number but each box still carries its own barcode. That is a business-account feature, not a way to reuse one retail label. For ordinary counter and online labels, the rule stands: one box, one label.

How do I keep multiple boxes straight?

Number the boxes yourself: write "Box 1 of 3", "Box 2 of 3", and so on, on each box and on the packing slip inside it. Keep a simple list for yourself: box number, tracking number, and contents. Send the recipient the same list, or at least the count and the tracking numbers, so they know when the delivery is complete and when a box is still missing.

When boxes look alike, the numbering matters even more. Identical brown boxes with identical address labels are easy to confuse at a busy receiving dock. A big marker number on two sides of each box takes seconds and prevents a "we only got two" dispute when the third box is sitting in another room.

SituationWhat to doWhy it matters
Two or three boxes, one orderOne label per box, numbered 1 of 3, 2 of 3, 3 of 3Recipient knows when the order is complete
Boxes of very different sizesLabel each with its own weight and sizeA shared label would misstate at least one box
One box arrives, others do notTrack each number separately, then contact the carrierEach tracking record is independent
Returning a multi-box orderReturn each box under its own return labelThe same one-label rule applies in reverse

Will the boxes arrive together?

Not always. Boxes dropped off together often travel together, but sorting can split them across trucks, and a large box may move on a different vehicle than a small one. Deliveries can land on different days, and a signature box may be held while a smaller box is left at the door. Tell the recipient to expect separate arrivals, and not to report a box missing until a reasonable window has passed for the slower box.

If the boxes must arrive together, say for an event or an installation, ship them early enough that a split delivery still lands in time. Some carriers offer a hold-for-pickup option, where all boxes wait at a depot or outlet for one collection trip, which suits a recipient who would rather collect everything at once than chase separate deliveries.

Can I strap boxes together to make one parcel?

Strapping or taping two boxes together does not make them one parcel in the carrier's eyes, and it usually makes things worse. Strapped boxes shift, the strap cuts into cardboard, and the combined shape measures as an oversize parcel with a higher price. If the strap breaks in transit, you are back to two unlabelled boxes. Pack the contents into one larger box instead, or ship them as two properly labelled parcels.

What about duties on multiple boxes?

For cross-border shipments, each box gets its own customs declaration, with its own contents and value. Splitting one order across boxes does not split the duty bill in your favour: customs can treat the boxes as one shipment and total their values. Declare each box honestly, with the same order reference on each form, so the receiving customs office can match them up.

Can I use LetterAgent labels for multiple boxes?

Yes, one label per box. LetterAgent provides Canada Post Xpresspost shipping labels for parcels within Canada, up to 5 kg each. You ask your AI assistant for a label for each box, approve each exact quoted price, pay once per label through Stripe, and receive a label PDF for each box. The same limits apply to every box: parcels over 5 kg and shipments outside Canada need another carrier.

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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