How to Send Multiple Letters at Once to Different Addresses

To send multiple letters at once to different addresses, first answer one question: does the letter itself change from person to person?

Use the Cart for separate PDFs that contain different letters. Use Bulk Send with a shared PDF when the letter stays identical for everyone. If names, greetings or other details must change inside the letter, use Bulk Send with a compatible letter template and matching CSV columns.

Postmarkr prints and mails the letters, and each recipient gets a separate mailing record. Before uploading, decide which content belongs to each recipient and confirm the addresses.

Same letter or different letters? Decide first#

An office-move notice with identical text suits a shared PDF. A client letter beginning “Dear Maya” needs a template if that greeting must change for each recipient. Separate, already-written thank-you letters suit the Cart. The spreadsheet mailing guide explains template preparation and the workflow in more detail.

Send different letters to different people: use the Cart#

For example, you have a signed thank-you letter for a client and a different letter for a conference speaker. Keep the files and recipients paired throughout these steps.

1. Save one PDF per letter. If they came back as one long document, split it into separate files first. Postmarkr mails each uploaded file as one letter; it doesn't split a combined file for you.
2. Get each one signed before you upload. We print what's in the PDF and can't add a signature. If you sign for your executive, how to sign a letter on behalf of your boss covers p.p., initials and when not to.
3. Start a letter, upload the first PDF and pick the recipient. Choose a usable US return address you have permission to use, such as your executive’s office. Check the recipient, return address, signature and page layout in the preview.
4. Choose "Add to Cart to send several together" instead of paying. Repeat for each letter.
5. Open the Cart and select up to 10 letters for checkout. Match each selected file to its recipient before paying. If more letters are ready, send the remaining selection in a separate checkout.

Each letter is priced for its own document and print settings. Review the final total before payment. If an older uploaded document has expired, follow the re-upload prompt and check the new preview before paying.

After payment, each letter has its own status page. Check its milestones for progress, and download the production PDF once it is available. A payment receipt alone does not show that USPS has the letter.

One letter to a whole list: Bulk Send, in short#

Choose one shared PDF or a compatible letter template for the batch. With a shared PDF or a template without custom fields, add recipients from a CSV, your address book or both. A template with custom fields needs CSV values for those fields. The batch uses one return address. Review accepted recipients and errors before payment. For a template, inspect the personalized proof, including a row with a long name or an optional field left blank. Regenerate the proof if changes make it out of date. The spreadsheet mailing guide covers merge fields; the Bulk Send overview covers the service and checkout limits.

Get the mailing list ready before you upload#

Suppose your holiday list and event list contain different addresses for the same client. Choose the current address before exporting; uploading both versions does not tell Postmarkr which one is right.

1. Choose the recipients and their current addresses. Keep a master sheet with a mailing category, then export only the people intended for this batch. Combine a person’s name into the name column, keep apartment or suite details, and confirm an address if the source lists disagree.
2. Use the supported column names. The required headers are name, address_line1, city, state and zip. Add address_line2 for apartments or suites; it may be blank. For personalized templates, use the sample CSV supplied for that template so its declared merge-field names match. The spreadsheet guide explains that setup.
3. Keep ZIP codes as text before entering or importing them. A ZIP such as 02116 must retain its leading zero. If the source has already lost it, check the correct ZIP rather than guessing. After exporting, open the CSV in a text editor and confirm the actual value is still 02116; a spreadsheet’s displayed formatting alone is not a reliable check of the exported file.
4. Resolve duplicate people, not just duplicate rows. Bulk Send compares the name and address fields, ignoring case and extra spacing, across CSV and selected address-book recipients. It does not reliably identify “Pat Smith, 12 Oak St” and “Patricia Smith, 12 Oak Street” as the same person. Different names at one address can remain separate recipients, so decide whether a household should receive a joint letter or separate letters.
5. Reconcile the import result with your intended list. Valid rows can be accepted while invalid or duplicate rows are excluded. Review those results and fix the affected rows before checkout; do not assume the whole file either passed or failed. An accepted import row does not prove that the named person still receives mail there or guarantee delivery.
6. Keep the corrected source list. Accepted CSV recipients are saved to the address book when you complete the import, before payment. Saving an address does not mail a letter. Keep corrections in your master sheet too, so the next export does not reintroduce old mistakes.

CSV shape example (fictional recipient; replace every value with your mailing data). The empty field between the commas after the street leaves address_line2 blank:

name,address_line1,address_line2,city,state,zip
Alex Example,123 Example St,,Boston,MA,02116

For a template with a declared field named greeting, add a greeting column and a value such as Dear Alex. That field must already be used in the template. Adding a greeting column to a shared-PDF batch does not personalize the PDF.

Questions assistants ask#

How many letters can I send at once?#

The Cart supports up to 10 letters per checkout. Bulk Send supports up to 100 recipients per batch and also applies an order-total cap. Split larger selections into separate checkouts or batches, and check the final total before paying.

Can Postmarkr mail our holiday cards?#

We don't print cards, use card stock or write by hand. We mail printed letters, so a year-end letter on your executive's letterhead is the closest thing we can send.

Will a merged letter look personal?#

A template can personalize the fields you build into it, such as a greeting or client detail. A shared PDF cannot: its letter content stays the same for every recipient. Both are printed letters in window envelopes. Review the personalized proof instead of assuming a CSV column will automatically appear in the letter.

Can I schedule a batch for a future date?#

There are no scheduled sends. Pay when you are ready for processing to begin, and leave time for both production and postal delivery. Review the First-Class delivery guide when planning a mailing deadline; payment does not reserve a delivery date.