Guide
How to check expense claims against your policy with AI
AI can do the first pass on expense claims before an approver sees them, as long as it works from your written policy. Give it the policy and the claim, and ask for every line marked pass, flag or fail with the rule quoted, the receipts that are missing, the total that's out of policy, and one question for each flag that the approver can send the employee. Two rules keep it fair: anything the policy doesn't cover is a flag, never a fail, and for per-person limits it divides by the attendees listed. The approver still decides; the check means they read questions, not every receipt.
Short answer
- Work from the written policy, quoted in every decision.
- Pass, flag or fail; not covered means flag.
- List missing receipts and total what's out of policy.
- One question per flag; the approver decides.
The brief to copy
Expense check brief
"Check this expense claim against our policy below.
One row per expense: date, merchant, amount, category. If a receipt total differs from the claimed amount, use the receipt and flag the difference.
For each line: pass (meets every rule), flag (something missing or unclear, or the policy doesn't cover it) or fail (clearly breaks a written rule). Quote the rule. For per-person limits, divide by the attendees listed.
List missing receipts. Total passed, flagged and failed, and the amount over each limit.
Write one question per flag that I can send the employee.
Policy: [paste]. Claim and receipts: [paste]"
A worked example
Illustration: a made-up business and policy. A 30-person company's policy says: meals with clients up to 60 per person with the attendees named; taxis need a receipt; hotels up to 180 a night. An account manager's claim for a two-day client visit comes back:
| Line | Result | Reason |
|---|---|---|
| Hotel, 1 night, 165 | Pass | "Hotels up to 180 a night" |
| Client dinner, 210, three people | Fail | 70 per person; "up to 60 per person": 30 over |
| Taxi, 38 | Flag | No receipt attached |
| Airport lounge, 45 | Flag | The policy doesn't cover lounges |
Out of policy: 30, the part over the dinner limit. Questions for the employee: "Can you add the taxi receipt?" and "The policy doesn't mention airport lounges; what was this for?" The finance lead approves the hotel, asks the two questions, and adds a lounge rule to the policy.
Set it up for the team
- Write the policy down with numbers; the check can't enforce "reasonable".
- Use one brief for everyone who approves, so claims are checked the same way.
- Keep card numbers and personal details out where the check doesn't need them, and use the company's approved account.
- Add a rule whenever the same flag comes back twice.
- Keep the approver's decision and the employee's answer with the claim.
Missing receipts matter beyond the policy. In the US, IRS Publication 463 says you generally need documentary evidence, such as receipts, canceled checks or bills, to support an expense, with exceptions such as an expense other than lodging under $75. A policy can ask for more than that, and the check follows the policy.
Next step: make it a skill
A brief everyone pastes drifts; a skill doesn't. Claude skills for finance covers the finance skills to set up first, and client data and AI in finance covers what may go in.
Skills for this
- FinanceExpense policy checkChecks expenses against your expense policy, line by line: pass, flag, or fail with the rule quoted, missing receipts, and out-of-policy totals.
- Operations and adminVendor invoice check before paymentChecks a vendor invoice against the PO or quote: details, arithmetic, tax, terms, duplicates, and changed bank details; returns approve or hold.
- FinanceMonth-end close checklistBuilds a month-end close checklist for a small company: reconciliations, accruals, deferred revenue, payroll, and review, with owners and day offsets.
- FinanceSaaS spend reviewReviews SaaS subscriptions: owners, seats used vs paid, overlapping tools, renewal and notice deadlines, and cancel, downgrade or keep with savings.
Questions
Can AI check expenses against our policy?
Yes, as a first pass before the approver. Give it the written policy and the claim, and ask it to mark each line pass, flag or fail, quote the rule behind each decision, list missing receipts, and total what's out of policy. Anything the policy doesn't cover is a flag, never a fail, and the approver decides.
What is the difference between a flag and a fail?
A fail clearly breaks a written rule, such as a meal over the per-person limit. A flag may be fine but something is missing or unclear, such as a vague purpose or a case the policy doesn't cover. Flags go back to the employee as a question.
Is it safe to put receipts into an AI tool?
Use a business account that doesn't train on your data by default, and the tool your company approved for finance data. Receipts can carry card numbers and personal details; remove them where the check doesn't need them.
AI skill
Have your AI check expenses against your policy
Put this skill in AI Skill Pod and everyone on your team gets it in their Claude, Cursor or ChatGPT (Pro, Business, Enterprise): one invite link, free to start. Expense policy check has your AI check each expense claim: each line against your written policy, marked pass, flag or fail with the rule quoted, missing receipts listed, the out-of-policy amount totalled, and a question for each flag.
14 days free · No card needed
Sources
- IRS Publication 463: Travel, Gift, and Car Expenses — Recordkeeping: you must generally have documentary evidence, such as receipts, canceled checks or bills, to support your expenses; not needed for an expense, other than lodging, of less than $75, or a transportation expense for which a receipt isn't readily available (read 2026-11-05)
- Anthropic Privacy Center: commercial products — not used for training by default (read 2026-11-05)