Match a tax-prep checklist against a receipts folder with Claude Cowork

Posted

Mar 18, 2026 by Bharat Mediratta (@bharat)

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Last checked

Oct 16, 2026

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Method:

How we verify

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Outcome

The poster says matching a spreadsheet of items for their accountant against a folder of receipts usually took 4–6 hours, and that with Claude Cowork it took about an hour.

Agent

Claude Cowork

The source didn't share its exact prompt, so we wrote this from what it describes.

Here's a task I'd like your help with. Read it all the way through before you start.

Goal: Match my tax checklist spreadsheet against the receipts in my folder, so I know what's ready for my accountant and what's missing.

Check with me first: Which tax year is this for?

What I'll give you:
- The spreadsheet where I track what to send my accountant
- The folder where I drop my receipts

Rules:
- Go through each line in the spreadsheet and find the matching receipt.
- Mark which items have a receipt and which are missing.
- If you're not sure a receipt matches, flag it and ask me.
- Don't delete or rename files without asking.

Output: The spreadsheet updated with a match for each item, plus a list of missing receipts.

If anything here is unclear or missing, ask me instead of guessing.

You'll know it worked when: I can see at a glance what's ready to send and what I still need to find.

Here's a task I'd like your help with. Read it all the way through before you start.

Goal: Match my tax-prep checklist against my receipts folder so I know what's ready for my accountant and what's missing.

Quick check first: tell me if anything below is missing or unclear.

Inputs (fill in or confirm):
- Checklist spreadsheet
- Receipts folder
- Tax year
- How I name or tag files
- What counts as a valid receipt for my accountant

Rules:
- For each checklist item, find matching receipts by vendor, amount and date.
- Mark each item: matched (with file name), partial, or missing.
- List receipts that don't match any checklist item.
- Don't move or rename files.
- Use fuzzy matching for vendor names (e.g. 'AMZN' = Amazon) and say when you did.
- Add totals: matched amount vs checklist amount.
- Note receipts that look personal, not business.

If you get stuck: If a match is uncertain, mark it 'check' with your reason. If a login, CAPTCHA or two-step code appears, stop and ask me to handle it; never guess or store passwords.

Verify before you finish: Re-open a sample of matches to confirm amounts.

Output: Updated checklist with status and file links, plus an unmatched-receipts list.

Done when: I can see at a glance what's ready and what's missing.

Source

https://x.com/bharat/status/2034068158123020569