More in Money, Bills & Taxes.
Find $6,000 in extra tax deductions with Claude Cowork
WorkedEvidence: Described by posterPosted Last checked
Viveka von Rosen's Claude Cowork review of tax-prep files surfaced an additional $6,000 in deductions after an extension filing.
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Review my tax-prep folder and connected books for the year. Ask what else you need, then find missed deductions, mislabeled expenses and anything that might change my bracket. Quote each find with the source document. Do not file anything.
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Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish. Goal: Find missed deductions and mislabeled expenses in my tax-prep files. Questions to ask me first: - Which tax years and entities (personal vs business)? - Which folders and connectors can you access? - Who will review before filing? Inputs (fill in or confirm): - Years: [2025 / 2026] - Folder: [TAX PREP PATH] - Connectors: [ACCOUNTING / STRIPE] - Extra exports: [AMAZON / BANK / PAYPAL / VENMO / CARDS] Rules: - List each proposed deduction with the source file. - Flag mislabeled categories instead of silently fixing books. - This is preparation for a human/CPA review, not filing advice. - Never submit returns or send messages to the IRS. Checkpoint: After inventorying files, list gaps before deep review. If you get stuck: If a statement is missing months, stop and ask rather than extrapolating. Verify before you finish: Every dollar claim ties to a document name I can open. Output: A ranked list of finds with sources and open questions for my CPA. Done when: I can hand the list to a tax professional before filing.
AI tool
Outcome
Viveka von Rosen ran 2025 and 2026 tax-prep documents through Claude Cowork after filing an extension. With folder access, an accounting-software connector, Stripe, and downloads of Amazon orders, bank statements, PayPal, Venmo, Trello VA invoices and credit-card statements, Claude Cowork found an additional $6,000 in deductions—enough, von Rosen says, to change tax brackets—and flagged mislabeled transactions. The author stresses this is a personal story, not tax advice, and plans to confirm with proper filing.
Evidence: Described by posterThe person describes what happened in words, without screenshots or video.
Source
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- by Viveka von Rosen
- Last checked
- Method:
- How we verify
https://vivekavonrosen.substack.com/p/claude-paid-for-itself-yesterday
Context: Author explicitly says this is not CPA advice. Confirm every deduction with a tax professional before filing.
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