Can AI file my business taxes?

Nah. Tax rules are specific, change yearly and mistakes cost money. AI can organize your records and questions for your tax preparer, but don't rely on it to file.

Verdict: Nah · Do it yourself✓ Tested 2 times in Llama 3.3 70B · Oct 28, 2026Written for ChatGPT, Claude or Gemini

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Nah

01Why nah

  • Tax law details and forms change every year.
  • AI can state rules that are wrong or outdated.
  • Organizing receipts and categories is where it helps.
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02The prompt

Replace everything in [BRACKETS] with your own details, then paste it into your AI app.

prompt.txt
You are a bookkeeper preparing records for a tax professional. This is not tax advice.

Business type: [SOLE PROPRIETOR, LLC, ETC.]
My expense list (paste it): [EXPENSES]
Income sources: [SOURCES]

Your task: organize my records for my tax preparer.

Rules:
- MUST group expenses into clear categories and total each one.
- MUST list anything unclear as a question for my preparer.
- NEVER tell me what's deductible as fact.

Give me: a categorized summary with totals and a list of questions for my preparer.

03Steps

  1. Export your income and expenses.
  2. Run the prompt.
  3. Bring the summary to a tax professional.

04What can go wrong

  • Tax mistakes can mean penalties.
  • Keep receipts; summaries aren't proof.

05What to use

Any major AI chat app, for organizing only.

06Our test runs

2 runs, each with a different made-up sample. 2 of 2 passed every check.

Run 1 · Llama 3.3 70B · graded by GPT-OSS 120BOct 5, 2026Passed

The made-up sample:

  • [SOLE PROPRIETOR, LLC, ETC.]Sole Proprietor
  • [EXPENSES]Office rent (Jan-Dec 2025): $12,000 Utilities (electricity, water, internet): $3,600 Office supplies (paper, printer ink, pens): $850 Marketing (online ads, flyers): $2,200 Travel (client meetings, mileage): $1,150 Professional services (accounting, legal): $1,800 Insurance (general liability): $1,200 Software subscriptions (accounting, design): $960 Meals and entertainment (client meals): $420 Bank fees and merchant processing: $310
  • [SOURCES]Website design services (project fees): $45,000 Monthly retainer for SEO consulting: $18,000 Sales of digital templates (Shopify store): $7,500 Affiliate commissions from marketing partners: $2,200 Workshops and webinars (ticket sales): $3,600
  • MUST group expenses into clear categories and total each one
  • MUST list anything unclear as a question for my preparer
  • NEVER tell me what's deductible as fact
  • Give me a categorized summary with totals and a list of questions for my preparer
  • Didn't make up details we never gave it

What came back (excerpt):

**Rent and Utilities**: - Office rent: $12,000 - Utilities: $3,600 Total: $15,600 2.
Read the full answer
**Categorized Summary:**

1. **Rent and Utilities**: 
   - Office rent: $12,000
   - Utilities: $3,600
   Total: $15,600

2. **Office Expenses**:
   - Office supplies: $850
   - Software subscriptions: $960
   Total: $1,810

3. **Marketing and Advertising**:
   - Marketing: $2,200
   Total: $2,200

4. **Travel**:
   - Travel: $1,150
   Total: $1,150

5. **Professional Fees**:
   - Professional services: $1,800
   Total: $1,800

6. **Insurance**:
   - Insurance: $1,200
   Total: $1,200

7. **Banking and Merchant Fees**:
   - Bank fees and merchant processing: $310
   Total: $310

8. **Meals and Entertainment**:
   - Meals and entertainment: $420
   Total: $420

**Income Summary:**

1. **Services**:
   - Website design services: $45,000
   - Monthly retainer for SEO consulting: $18,000
   Total: $63,000

2. **Product Sales**:
   - Sales of digital templates: $7,500
   Total: $7,500

3. **Commissions**:
   - Affiliate commissions: $2,200
   Total: $2,200

4. **Workshops and Webinars**:
   - Workshops and webinars: $3,600
   Total: $3,600

**Questions for Tax Preparer:**

1. Are there any specific requirements for documenting business use of the office space to support the office rent expense?
2. How should the travel expenses be broken down between business and personal use, if applicable?
3. Are there any limitations or special rules for deducting meals and entertainment expenses?
4. Do any of the software subscriptions qualify as capital expenditures or should they be expensed?
5. Are there any additional records or documentation needed to support the affiliate commissions as business income?
6. How should the income from workshops and webinars be reported, and are there any specific tax implications for this type of income?
7. Are there any other expenses that could be categorized under a different heading for tax purposes?

Check that no deductible advice is given and all expense totals are correct.

Run 2 · Llama 3.3 70B · graded by GPT-OSS 120BOct 28, 2026Passed

The made-up sample (a messier one):

  • [SOLE PROPRIETOR, LLC, ETC.]LLC (single‑member, taxed as sole proprietorship)
  • [EXPENSES]Office rent – 1200 per month (Jan‑Dec) Internet service – 80/mo Phone line – 55/mo Software subscription (Adobe CC) – 52.99/mo Software subscription (QuickBooks) – 30/mo Office snacks (coffee, granola bars) – $45.20 total Client dinner 7/12 – $112.50 (restaurant) Car fuel – 150.75 (business mileage) Travel to conference – flight $420, hotel $310, meals $95 Advertising – Facebook ads $230.40 Printer ink – $38.60 Bank fees – $12.00 Consultant fees – "John Doe" $600 (unspecified services) Tax software – 2024 version $149.99 Coffee beans for office – $27.30 Uniforms – $0 (none purchased) Misc equipment – "Desk lamp" $22.00
  • [SOURCES]Website design services (client contracts) Monthly SEO retainer – $1,200/mo One‑time branding project – $3,500 Affiliate commissions – $420 (via blog) Online course sales – $2,150 (Udemy) Studio space rental – $800/mo
  • Group expenses into clear categories with totals
  • List unclear items as questions for preparer
  • Never state any expense is deductible
  • Provide categorized summary and question list
  • Didn't make up details we never gave it

What came back (excerpt):

**Office Expenses:** * Office rent: $14,400 (1200/month x 12) * Internet service: $960 (80/month x 12) * Phone line: $660 (55/month x 12) * Office snacks: $45.
Read the full answer
**Categorized Summary:**

1. **Office Expenses:**
	* Office rent: $14,400 (1200/month x 12)
	* Internet service: $960 (80/month x 12)
	* Phone line: $660 (55/month x 12)
	* Office snacks: $45.20
	* Coffee beans for office: $27.30
	* Printer ink: $38.60
	* Misc equipment (Desk lamp): $22.00
	Total: $16,152.10
2. **Software and Subscriptions:**
	* Adobe CC: $635.88 (52.99/month x 12)
	* QuickBooks: $360 (30/month x 12)
	* Tax software: $149.99
	Total: $1,145.87
3. **Travel and Entertainment:**
	* Client dinner: $112.50
	* Travel to conference: $825 (flight $420 + hotel $310 + meals $95)
	Total: $937.50
4. **Advertising:**
	* Facebook ads: $230.40
	Total: $230.40
5. **Fuel and Transportation:**
	* Car fuel: $150.75
	Total: $150.75
6. **Professional Fees:**
	* Consultant fees (John Doe): $600
	Total: $600
7. **Bank Fees:**
	* Bank fees: $12.00
	Total: $12.00
8. **Income:**
	* Website design services: unknown (multiple client contracts)
	* Monthly SEO retainer: $14,400 (1200/month x 12)
	* One-time branding project: $3,500
	* Affiliate commissions: $420
	* Online course sales: $2,150
	* Studio space rental: $9,600 (800/month x 12)

**Questions for Tax Preparer:**

1. Are the consultant fees paid to John Doe for a specific business purpose, and if so, what is the nature of the services provided?
2. Can the cost of coffee beans for the office be considered a business expense, and if so, under what category?
3. Are the expenses for the travel to the conference (flight, hotel, meals) eligible for business expense treatment, and if so, what documentation is required to support these expenses?
4. How should the income from website design services be reported, and what documentation is required to support this income?
5. Are there any specific requirements or limitations for deducting business expenses related to the use of a home office or studio space rental?

Check that no statements declare expenses as deductible.

How each run works: we fill the prompt with a made-up sample, run it once in Llama 3.3 70B, and GPT-OSS 120B grades the answer against the prompt's own rules. Word limits are counted by code, and every quote flagged as made up is checked against the full answer. Your results can differ. How we test.

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