LetterAgent
Mail physical letters by just asking your AI assistant.
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Yes, in an envelope you mail yourself, a photo can ride along with a letter. LetterAgent is different: it prints letters only, with no inserts, so a photo cannot be tucked into a LetterAgent mailing. Print the photo into the letter itself instead, or mail the photo separately in your own envelope.
The main change is thickness and stiffness. A standard letter envelope runs through sorting machines that bend and squeeze mail at speed. A single flat photo usually passes through fine, but a stack of photos, a photo mounted on card, or a photo in a stiff sleeve can jam a machine or get flagged for hand sorting. Hand sorting is not a penalty, but it can slow delivery and, in some cases, change the postage class.
Weight matters too. Photos on resin-coated paper are heavier than plain letter paper, and a few of them can push an envelope over the first weight step. If you are mailing the letter yourself, weigh the sealed envelope or have it weighed at the counter rather than guessing. An underpaid envelope can come back to you or arrive with postage due for the recipient, which is a poor surprise to pair with a nice photo.
| Photo format | What to watch for |
|---|---|
| Single loose print | Usually fine; keep it flat against the letter pages |
| Several prints | Weight and thickness climb fast; weigh the sealed envelope |
| Photo on card stock or mounted | Stiffness can force hand sorting; use a larger envelope |
| Instant film prints | Thick and stiff; one or two only, and protect the image surface |
| Printed into the letter page | Works with LetterAgent, since the letter is printed as one document |
Slip the photo between the folded letter pages or inside a plain sheet of paper, with the image side facing the paper rather than the envelope wall. That keeps the surface from picking up scuffs from the envelope's seams and glue. Never use a paper clip on a photo you care about: clips dent the surface and leave rust marks if the envelope gets damp.
For a photo with real sentimental value, send a copy and keep the original. Home printers now produce prints good enough that most recipients will not notice the difference, and a reprint costs far less than the regret of losing the only copy of a childhood picture. If the photo is the point of the letter, say so in the letter itself, so the recipient knows to look for it and does not toss the envelope with the photo still inside.
Yes, but cross-border mail has its own quirks. A photo inside a letter to another country is still a letter for most postal services, as long as the envelope stays flat and light. Once it gets thick or rigid, some carriers start treating it as a parcel, which can mean a customs form and a different price. Keep international photo mail thin and flat, and check the destination country's rules for anything that looks like commercial goods.
One practical trap: some countries' customs offices open and inspect thicker envelopes. A photo is not dutiable in the usual sense, but an opened envelope can arrive resealed with a customs sticker, and a loose photo can slip out during inspection. A photo printed into the letter page avoids that risk entirely, since there is nothing loose to lose.
LetterAgent prints your letter on letter-size paper, single-sided, and mails it in a double-window business envelope. The recipient's address shows through one window and your return address through the other. There are no inserts, flyers, or return envelopes, just the letter. That rule keeps the mailing machine-readable and predictable, but it means a separate photo cannot ride along.
The workaround is simple: put the photo into the letter document itself, as an image on one of the pages, before you ask your assistant to send it. Black-and-white or colour printing is available, and the page count is verified in your quote before you approve the exact price. If the photo must arrive as a standalone print, mail that envelope yourself and use LetterAgent for the letter. The two can arrive on different days, so mention the photo in the letter if the timing matters.
Do not mail original negatives, one-of-a-kind vintage prints, or photos with writing on the back in soft pencil that could smudge. Ballpoint on the back is safer, and a light label on the back beats writing directly on an old print. Also skip glossy photo paper in a damp climate without a plastic sleeve: moisture can glue a glossy print to the envelope wall, and peeling it off takes the image with it.
For official purposes, such as a passport or visa photo, the rules are stricter and set by the receiving agency, not the post office. Those photos have size, background, and recency rules of their own, and a casual print tucked into a letter will not pass. Check the agency's photo rules first, and treat that as a separate task from writing the letter.
Ready to mail it? Send your letter with LetterAgent: describe it to your AI assistant, approve the exact quoted price, and it is printed and mailed.
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.
Need help? Ask your assistant: it can check a job's status any time. If it ever can't handle something: hello@getletteragent.com