LetterAgent
Mail physical letters by just asking your AI assistant.
Mail it with tracking and proof: send the check by certified mail (US) or registered mail (Canada) so you have a receipt showing when you mailed it and a record of delivery. Keep a copy of the check and the mailing receipt. If the landlord later says it never arrived, that paper trail is what settles the argument.
Plenty of landlords still run on paper: small landlords with no payment portal, owners who don't trust payment apps, or leases that specifically call for check or money order. A mailed check also creates a physical record both sides can hold, which matters when the relationship sours. And in some markets, rent paid by check on the 1st is simply the norm the lease describes: follow the lease first, and use the method it names.
| Service | What you get | When it's worth it |
|---|---|---|
| Regular first-class mail | Nothing at all: the piece travels untracked | Never, for rent |
| Certificate of mailing (US) | A post-office receipt proving the date you mailed it | Cheap date proof that the payment went out on time |
| Certified mail (US) / Registered mail (Canada) | Mailing receipt plus tracking plus a delivery record | When you want the full chain: sent, tracked, delivered |
The catch people miss: certified mail proves the envelope was delivered, not what was inside it. If the dispute is "you never sent the check," the certified receipt wins. If the dispute becomes "the check was blank" or "it was for the wrong month," you need a photocopy of the filled-in check kept at home. Date proof plus content proof beats either one alone, and the copy costs you nothing to keep.
Use the memo line for the rental month and unit, not the dollar amount: "October 2026, Unit 4B." That ties the payment to a specific month if a dispute later arises about which month got paid. Fill in the payee exactly as the lease names the landlord or management company, and never leave the payee line blank "to fill in later": a signed check with a blank payee line is as good as cash to whoever finds it.
Don't postdate the check without an agreement. Some tenants postdate hoping the landlord will hold it, but nothing obliges the landlord to wait: many deposit it the day it arrives, and an early deposit against a thin balance means a bounced check plus a bank fee. If you need the landlord to hold the check, get that in writing first.
Work the paper trail in order. First, check the tracking: if it shows delivered, give the landlord the delivery date and ask them to check with household members or their office staff. If tracking shows the piece lost, or there was no tracking at all, put a stop payment on the check through your bank, then reissue. Never send a second check while the first might still surface: two live checks for one month's rent is how you pay twice.
Keep every receipt, and put the follow-up in writing. Even a short email counts: "Confirming our call today, I'm reissuing the October check after the original was lost in transit." Written records win the disputes that verbal ones lose, because memories of phone calls fade and timestamps don't.
Not the check itself. LetterAgent prints and mails letters (8.5x11, single-sided, no inserts), so there's no way to include your physical check in the envelope. What it can mail is everything around the check: a cover letter noting the payment, a formal notice to the landlord, or a written record of a payment dispute. For the check itself, use certified or registered mail yourself and keep the receipt.
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.
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