Tracked letters for ShipStation orders

PigeonTrail reads ShipStation's order export as it downloads, prints each order on an envelope with the address and a USPS barcode, and follows every letter scan by scan. Back in ShipStation you mark those orders shipped without a label, and each marketplace's own tracking rules still decide which orders can go as letters.

Updated October 21, 2026

A #10 envelope printed by PigeonTrail: the shop's return address at the top left, a box for the Forever stamp at the top right, and the buyer's address with a USPS barcode above it.

How do I export orders from ShipStation?

ShipStation's help gives the steps: on the Orders tab, select the orders, click Other Actions, then Export Orders, and choose whether you want Export Orders or Export Order Line Items. PigeonTrail reads either file. The export includes the Ship To address, the order total and the customer's email address.

How do I bring ShipStation orders into PigeonTrail?

Drop the file on the Orders page in PigeonTrail, as it came from ShipStation. PigeonTrail recognizes the file by its column names, so you don't rename or delete anything first, and when an order has one row per item, the rows are folded back into one order. Each address is checked against USPS data before anything prints, and an address USPS can't match is flagged so you can fix it with the buyer. PigeonTrail mails only to addresses in the United States.

PigeonTrail uses the Ship To name and address, never the Bill To name, and a line items export with one row per product is folded back into one order. When the file carries each order's value, orders of $50 or more go to a separate Packages list instead of your letters, with a file you upload to Pirate Ship to buy Ground Advantage labels. You can change that $50 line in Settings, or turn it off.

How do I print tracked envelopes?

Pick the orders, choose what to print on and print from your own printer. PigeonTrail prints #10, #9, #6 3/4, A7 and 6 x 9 envelopes, Avery 5163 address sheets, 4 x 2 and 4 x 6 thermal labels, and a window slip that folds into a #10 window envelope. Each one carries the buyer's address and a USPS Intelligent Mail barcode in the places USPS's machines read them, with your return address and, if you like, your logo. You add a Forever stamp, which is $0.82 for a 1 ounce letter, and drop the letters in the mail.

The barcode only gets scanned when the letter goes through USPS's sorting machines, so keep it flat and flexible. Our letter checker tells you whether a mailer counts as a letter, whether it is machinable and how many stamps it needs.

What does my buyer see?

Every letter gets a tracking page with your shop's logo and colors, a map of the route so far and the day USPS expects it to arrive. When the export carries the customer's email address, we email your buyer the tracking link at the first USPS scan. Amazon orders in ShipStation carry Amazon's relay addresses, which accept mail only from the seller, so PigeonTrail skips those. If you're on Pro, the emails come from your shop's name, and your buyer hears from you when the letter is mailed, when it's almost there and when USPS marks it delivered.

A letter's scans come from USPS's sorting plants, and its delivered event is USPS's estimate from the carrier's route rather than a scan at the mailbox. Our guide to what each USPS scan means explains what your buyer will see.

How do I mark letters as shipped in ShipStation?

Use Mark as Shipped, which ShipStation's help says "moves orders and shipments to the Shipped status without creating a label." You pick the carrier, enter a tracking number only if you have one, and choose whether to notify the customer and the marketplace. ShipStation says orders marked this way count toward your plan's monthly shipment limit and that it gets no tracking updates for them, so the letter's scans stay in PigeonTrail.

Leave the tracking number empty for letters going to Amazon, eBay or Etsy orders, because those marketplaces check tracking with the carrier and can't see a PigeonTrail barcode's scans.

Which ShipStation orders can go as stamped letters?

That depends on where each order came from, because the marketplace's rules follow the order into ShipStation. Amazon exempts orders under $10 sent as USPS First Class Mail envelopes from its tracking rate, eBay counts its own Standard Envelope label, Etsy's protection needs valid tracking or an Etsy label, and TCGplayer wants carrier tracking over $49.99. PigeonTrail moves orders of $50 or more to a Pirate Ship list by default, and you can lower that line in Settings. Our pages for Amazon, eBay, Etsy and TCGplayer have each marketplace's details.

Questions

Does marking an order shipped in ShipStation cost a shipment?

ShipStation's help says orders marked as shipped count toward your subscription's monthly shipment limit, the same as orders with labels.

Will ShipStation show the letter's scans?

No. ShipStation says it receives no tracking updates for orders marked as shipped, so you follow the letter in PigeonTrail, where every USPS scan lands.

Does PigeonTrail need ShipStation to work?

No. ShipStation's export is one of the files PigeonTrail reads, and you can also bring orders straight from TCGplayer, eBay, Amazon, Etsy, Shopify or WooCommerce.

Sources

  1. ShipStation Help, "Export Order Records", last edited May 5, 2026, read October 21, 2026: help.shipstation.com
  2. ShipStation Help, "Mark Orders as Shipped", last edited March 25, 2025, read October 21, 2026: help.shipstation.com
  3. Amazon Seller Central help, "Valid Tracking Rate policy" (G201817070), read October 21, 2026: sellercentral.amazon.com
  4. TCGplayer, "How should I ship my TCGplayer orders?", read October 13, 2026: help.tcgplayer.com
  5. USPS, Informed Visibility Mail Tracking and Reporting release notes, September 2026, on piece data going only to the Mailer ID owner and the companies it delegates to: postalpro.usps.com

Print your next ShipStation batch with tracking

Your first 100 letters each month are free, and you don't need a card to start.