Can AI do my taxes?
Nah. AI can explain tax terms and help you get organized, but it shouldn't prepare or file your return. Mistakes cost real money.
01Why nah
- AI can state rules that are out of date or wrong for your state, with full confidence.
- It can't see your documents unless you share sensitive data you shouldn't paste into a chat.
- Tax software and qualified preparers check your numbers against current rules. A chat app doesn't.
02The prompt
Replace everything in [BRACKETS] with your own details, then paste it into your AI app.
You are a tax-prep organizer, not a tax preparer. Do NOT calculate my tax or tell me what to file. My situation in plain words: [e.g. W-2 job, a side gig, I rent, one kid] Give me: 1. A checklist of documents I should gather, grouped by type. 2. Plain-English meanings of any tax terms in my situation. 3. Questions I should ask tax software or a preparer. Rules: if a rule depends on the year or state, say so and tell me to confirm it. Say "I'm not sure" rather than guessing.
03Steps
- Use the prompt only to get organized.
- Prepare your return with tax software or a qualified preparer.
- In the US, check the IRS website to see if you qualify for free filing.
04What can go wrong
- Never paste your Social Security number or full account numbers into a chat app.
- Rules change every year. Treat anything AI says about amounts or limits as unconfirmed.
05What to use
06Our test runs
2 runs, each with a different made-up sample. 2 of 2 passed every check.
The made-up sample:
[e.g. W-2 job, a side gig, I rent, one kid]Full‑time W‑2 job at Acme Software (salary $68,000), freelance graphic‑design side gig earning about $12,500, rent a two‑bedroom apartment ($1,300/month), one child (age 5) with daycare expenses $4,200, and a modest 401(k) contribution of $3,500.
- Do not calculate tax or tell what to file
- Give checklist of documents grouped by type
- Explain tax terms in plain English
- Flag rules that depend on year or state and ask to confirm
- Didn't make up details we never gave it
What came back (excerpt):
I'd be happy to help you organize your tax information. Here are the items you requested:
Read the full answer
I'd be happy to help you organize your tax information. Here are the items you requested: **1. Checklist of documents to gather, grouped by type:** * **Income documents:** + W-2 form from Acme Software + 1099-MISC form(s) for freelance graphic design income * **Expense documents:** + Receipts for daycare expenses ($4,200) + Lease agreement and rent payment records for apartment ($1,300/month) * **Retirement account documents:** + 401(k) contribution statement showing $3,500 contribution * **Dependent documents:** + Birth certificate or social security card for your child + Proof of childcare expenses (e.g., daycare center invoices) * **Other documents:** + Any other relevant tax-related documents, such as interest statements from banks (1099-INT) or investment accounts (1099-DIV) **2. Plain-English meanings of tax terms in your situation:** * **W-2:** A form showing your income and taxes withheld from your full-time job at Acme Software. * **1099-MISC:** A form showing your freelance graphic design income. * **401(k) contribution:** A type of retirement savings plan where you contribute a portion of your income to a tax-deferred account. * **Dependent:** A person, such as your child, who relies on you for financial support and may qualify you for tax benefits. * **Daycare expenses:** Costs related to caring for your child while you work or attend school, which may be eligible for tax credits or deductions (rule may depend on the year and state, so confirm this). **3. Questions to ask tax software or a preparer:** * What tax credits or deductions am I eligible for based on my income, expenses, and dependent? * How do I report my freelance graphic design income, and what expenses can I deduct related to this business? * Can I claim a deduction for my rent payments, and if so, what documentation do I need? * How do I claim the childcare tax credit, and what expenses qualify? * Are there any other tax benefits or credits I may be eligible for based on my 401(k) contribution or other factors? * I'm not sure what other documents or information I may need to provide, can you guide me through the process?
Verify that no tax calculations or filing instructions were included.
The made-up sample (a messier one):
[e.g. W-2 job, a side gig, I rent, one kid]Full‑time W‑2 at a tech startup, freelance graphic‑design gigs, own a condo but also rent a spare bedroom, two kids (one in college, one in high school), 401(k) contributions, occasional crypto trades, recent divorce with alimony, and a $5k inheritance.
- Do NOT calculate my tax or tell me what to file
- Give a checklist of documents I should gather, grouped by type
- Plain-English meanings of any tax terms in my situation
- If a rule depends on the year or state, say so and tell me to confirm it
- Didn't make up details we never gave it
What came back (excerpt):
I'd be happy to help you organize your tax preparation.
Read the full answer
I'd be happy to help you organize your tax preparation. Here are the requested items: **1. Checklist of documents to gather, grouped by type:** * **Income documents:** + W-2 form from your full-time job + 1099-MISC forms for freelance graphic design gigs + Rental income statements (if you received rent from the spare bedroom) + Crypto trading statements (e.g., 1099-K, if applicable) + Inheritance documentation (e.g., letter from the estate administrator) * **Deduction and credit documents:** + Mortgage interest statement (Form 1098) for your condo + Property tax statement for your condo + Receipts for home office expenses (if you use a dedicated space for freelance work) + Receipts for education expenses (e.g., tuition, fees, for your college kid) + Receipts for childcare expenses (if applicable) * **Retirement and investment documents:** + 401(k) contribution statements + Crypto trading account statements * **Divorce and alimony documents:** + Divorce decree or separation agreement + Alimony payment records * **Dependent and child-related documents:** + Birth certificates or Social Security numbers for your kids + College tuition statements (if applicable) + Childcare provider information (if applicable) **2. Plain-English meanings of tax terms in your situation:** * **W-2:** A form showing your income and taxes withheld from your full-time job. * **1099-MISC:** A form showing income from freelance work or other non-employment sources. * **Alimony:** Payments made to your former spouse as part of your divorce agreement. * **Crypto trades:** Buying and selling cryptocurrency, which may be subject to capital gains tax. * **Inheritance:** Money or assets received from someone's estate after they pass away. * **Dependent:** A person, such as a child or relative, who relies on you for financial support. * **Head of Household:** A filing status that may apply to you if you're unmarried, have dependents, and meet certain requirements (check with your tax software or preparer to confirm). * **Itemized deductions:** Expenses you can claim on your tax return to reduce your taxable income, such as mortgage interest, property taxes, and medical expenses. **3. Questions to ask tax software or a preparer:** * What filing status should I use (e.g., Single, Head of Household, Qualifying Widow(er))? * How do I report my freelance income and expenses? * Can I deduct home office expenses, and if so, how do I calculate them? * How do I report my crypto trades, and what are the tax implications? * What are the tax implications of my inheritance, and do I need to report it on my tax return? * Can I claim my kids as dependents, and if so, what credits or deductions am I eligible for? * How do I report my alimony payments, and are they deductible? * Are there any specific rules or limitations for my state or local taxes that I should be aware of (e.g., regarding rental income, crypto trades, or inheritance)? * I'm not sure what other documents or information I might need to provide, can you guide me through the process? Please confirm the rules and regulations for your specific situation with your tax software or preparer, as some rules may depend on the year or state.
Ensure the response never calculates taxes or gives filing instructions.
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.