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Sometimes. Postage is deductible when it is a genuine cost of running a business, freelancing, or managing a rental property. It is not deductible when it is personal: birthday cards, holiday letters, and notes to friends buy you no tax benefit. This is general information, not tax advice.
The dividing line in one sentence: if the letter exists because of work you get paid for, the postage is a business expense; if it exists because of your personal life, it isn't.
| Situation | Deductible? | Why |
|---|---|---|
| Invoices, contracts, and client correspondence | Yes | Ordinary costs of running a business |
| Freelancer mailing portfolio samples or proposals | Yes | Part of earning self-employment income |
| Landlord mailing notices or lease renewals to tenants | Yes | Cost of managing a rental property |
| Birthday cards, holiday letters, thank-you notes | No | Personal expenses, however generous the sentiment |
| Postage on a job application you mailed yourself | Generally no | Job-search costs are personal expenses in most cases |
| Stamps donated to a charity's mailing | Talk to a tax professional | Rules for donated supplies are narrower than people expect |
In the US, business postage goes with your other business expenses: on Schedule C if you're self-employed, or through your company's books if you run one. The details that make it clean are boring ones. Keep receipts for postage purchases and mailing-service invoices, and keep a short note of the business purpose for anything unusual (a certified letter to a client, a bulk mailing for a campaign). A drawer of loose stamps with no records is still deductible in theory, but it's much easier to defend when your records show what the postage was for.
The same principle holds: postage is deductible as a business expense when it's incurred to earn business income, and personal postage isn't deductible. Canadian freelancers and businesses claim mailing costs among their operating expenses, with GST/HST on the postage handled according to how the business files. One Canadian wrinkle worth knowing: personal-use deductions that Americans sometimes ask about (like unreimbursed employee expenses) have largely disappeared in the US, and Canada never allowed most of them, so don't assume an employer's postage you paid out of pocket is deductible without checking the current rules.
Yes, if the letters are business letters. When you pay a service to print and mail a letter for you, the whole fee (print, postage, and service charge) is just a business mailing cost, same as buying stamps and paper yourself. Keep the payment receipt from the service the way you'd keep a postage receipt. The quote-then-approve flow helps here: the receipt shows exactly what the mailing cost, which is what a clean expense record needs.
Receipts for stamp purchases and mailing-service payments, plus a brief business-purpose note for anything that isn't obvious. That's the whole system. Tax authorities care about two questions: was this really a business expense, and can you show it. A receipt answers the second question; your note answers the first. For high-volume mailers, an annual statement from your mailing service or post-office account works the same way.
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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