Tax Planning Prompts That Actually Save You Money
16 ChatGPT prompts for deductions, credits, Roth conversions, capital gains optimization, business tax strategy, and the year-end moves that quietly save thousands.
In short: This page contains 16 copy-paste ready prompts, organized into 4 categories with a description and pro tip for each. The first 5 prompts are free instantly, no signup needed. Drafted with AI writing assistance and checked against our editorial policy.
Deductions + Credits
4 promptsItemize vs Standard Deduction
1/16✨ What it does
ChatGPT decides itemize versus standard for status [describe] against standard [amount], using mortgage, SALT, charity [$], and medical, plus bunching if you are close. Run the two totals yourself, then bunch gifts into one year if that tips you over.
Decide itemize vs standard deduction. Filing status: [describe]. Standard: $[amount]. Potential itemized: mortgage interest [$], SALT capped at $10K, charitable [$], medical >7.5% AGI. Include: math comparison, bunching strategy if close, year-over-year planning.
Pro tip: Post-TCJA most taxpayers take standard deduction. Bunching: combine 2 years of charitable giving into 1 year to itemize; standard the next. Same total; better tax outcome.
Charitable Giving Optimization
2/16✨ What it does
ChatGPT optimizes giving of [amount] for filing [describe] and income [amount], covering appreciated stock, DAFs, QCDs after 70.5, and AGI limits. Give the stock instead of cash when you can, then confirm the receipt with your tax software.
Optimize charitable giving. Annual giving: $[amount]. Filing: [describe]. Income: $[amount]. Include: cash vs appreciated stock (best!), DAF (donor-advised fund) for bunching, QCDs from IRA post-70.5, AGI limits (60% cash, 30% stock), carry-forward 5 years.
Pro tip: Appreciated stock > cash giving. Avoid capital gains tax + full FMV deduction. $10K appreciated stock = $10K deduction + saved $2-3K capital gains. Double win.
Tax Credits Scan
3/16✨ What it does
ChatGPT scans credits for family [describe], kids [ages], income [X], and activities [describe], including Child Tax, care, Saver's, EITC, learning, and clean energy. Check each credit you might qualify for in your software, then keep the documents.
Scan for tax credits I may miss. Family: [describe]. Kids: [ages]. Income: $[X]. Activities: [describe]. Include: Child Tax Credit, Child Care Credit, Saver's Credit, Earned Income Credit, Lifetime Learning Credit, Residential Clean Energy Credit, retirement contribution credits.
Pro tip: Credits > deductions (dollar-for-dollar vs deduction × tax rate). Child Tax Credit up to $2000/child. Energy credits 30% (solar, heat pumps). Worth 30 min to research annually.
Home Office Deduction
4/16✨ What it does
ChatGPT tests a home office deduction for [which] using [sq ft of home office, total sq ft], comparing simplified versus regular and noting W-2 employees cannot claim it. Measure the room, then skip the deduction if you are a W-2 employee.
Qualify for home office deduction. Self-employed / W-2: [which]. Office details: [sq ft of home office, total sq ft]. Include: simplified ($5/sq ft up to $1500) vs regular method, actual expenses (% of utilities, insurance, depreciation), W-2 employee can't claim (post-2018), audit risks.
Pro tip: Home office: must be "regular + exclusive" use. Desk in bedroom = probably not. Separate room = solid claim. Simplified method easier; regular method more deduction but more paperwork.
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Capital Gains + Investments
4 promptsCapital Gains Planning
5/16✨ What it does
ChatGPT plans capital gains for short-term [X], long-term [Y], and income [Z], covering 0/15/20% brackets, year-splitting, losses, and state tax. Time a sale only after you estimate the bill, including state.
Plan capital gains for year. Short-term (under 1yr) gains: $[X]. Long-term gains: $[Y]. Income: $[Z]. Include: LTCG brackets (0%, 15%, 20%), harvesting gains at 0% bracket, timing sales across years, offsetting with losses, state tax impact.
Pro tip: 0% LTCG bracket: single under $47K, married under $94K (2026). Harvesting gains in 0% bracket = tax-free wealth reset. Retirement years before Social Security = common 0% window.
Roth Conversion Strategy
6/16✨ What it does
ChatGPT sizes a Roth conversion of Traditional IRA [amount] at bracket [X] versus expected [Y] and income [Z], including IRMAA after 63 and the 5-year rule. Convert only what fills this year's bracket, and set aside cash for the tax.
Roth conversion strategy. Traditional IRA: $[amount]. Current tax bracket: [X]. Retirement bracket expected: [Y]. Income this year: $[Z]. Include: amount to convert (fill bracket without bumping), tax bill source, 5-year rule, Medicare IRMAA impact if 63+.
Pro tip: Roth conversion ladder: convert just enough to stay in current bracket. $10-30K/year typical. Avoid triggering Medicare premium hikes (IRMAA) after 63. Multi-year strategy.
Tax-Loss Harvesting
7/16✨ What it does
ChatGPT plans tax-loss harvesting from [current losses], with replacements, the wash-sale rule, the $3K income offset, and carry-forward. Sell and replace in one sitting, then log the carry-forward for next year.
Tax-loss harvesting plan. Portfolio: [current losses]. Include: specific candidates to sell, wash sale rules, replacement securities (30+ day similar not identical), $3K annual limit against income, unlimited vs gains, carry-forward.
Pro tip: Harvest losses December (close to tax year). $3K against ordinary income = $750-1100 tax savings (22-37% bracket). Plus losses against gains. Mechanical + valuable.
Mega Backdoor Roth
8/16✨ What it does
ChatGPT checks Mega Backdoor Roth eligibility from 401k [describe options, after-tax contributions allowed, in-service conversion] and contributions [describe], with a step-by-step conversion. Confirm after-tax and in-service options with HR before you send extra dollars.
Mega Backdoor Roth feasibility. Employer 401k: [describe options — after-tax contributions allowed? in-service conversion?]. Current contributions: [describe]. Include: eligibility check, contribution amount possible ($46K above 401k limit), conversion to Roth IRA mechanics, step-by-step.
Pro tip: Mega Backdoor Roth = $46K/year extra tax-free retirement contributions (above $23K 401k limit). Requires employer plan allowing after-tax + in-service conversion. Rare but powerful.
Business + Self-Employed
4 promptsSelf-Employment Tax Strategy
9/16✨ What it does
ChatGPT builds a self-employment tax plan for income [amount] under [sole prop, LLC, S-Corp], covering S-Corp break-even, SEP versus Solo 401k, expenses, and estimates. Talk to a CPA before an S-Corp election, then calendar the quarterly payments.
Self-employment tax strategy. Business income: $[amount]. Structure: [sole prop, LLC, S-Corp]. Include: S-Corp election break-even (~$60K net), reasonable salary rule, SEP-IRA vs Solo 401k, deductible business expenses checklist, quarterly estimated taxes.
Pro tip: S-Corp election saves 15.3% SE tax on distributions above reasonable salary. Worth it above ~$60K net SE income. Below = complexity not worth savings.
Solo 401k Setup
10/16✨ What it does
ChatGPT walks through a Solo 401k for income [amount], with employee and employer limits, Roth and Mega Backdoor options, and Fidelity, Schwab, or ETrade setup. Open the plan before the deadline, then fund both sides up to the real limit.
Set up Solo 401k for self-employed. Business income: $[amount]. Include: contribution limits ($23K employee + 25% employer, up to $69K total), Roth option availability, Mega Backdoor option, plan administrator (Fidelity, Schwab, ETrade), deadline requirements.
Pro tip: Solo 401k >>> SEP-IRA for self-employed. Higher limits + Roth option + loan feature + Mega Backdoor possible. Fidelity/Schwab free admin. Open before Dec 31 for current year.
Business Deduction Scan
11/16✨ What it does
ChatGPT scans deductions for business [describe], including home office, mileage, SE tax, health premiums, retirement, meals, software, and Section 179. Keep receipts for every item you claim, then drop anything that is not ordinary and necessary.
Scan business deductions. Business: [describe]. Include: home office, mileage (67 cents/mile 2026), half of SE tax, health insurance premiums, retirement contributions, business meals (50%), software + subscriptions, professional development, equipment (Section 179).
Pro tip: Section 179 allows full deduction of equipment up to $1.22M same year. Bonus depreciation phasing out. Document: receipts + business purpose for everything over $75.
Quarterly Estimated Taxes
12/16✨ What it does
ChatGPT calculates quarterly estimates from self-employment [amount], other income [Y], and deductions [describe], with federal, state, and safe harbor. Pay on the IRS calendar, or use safe harbor so a good year does not trigger a penalty.
Calculate quarterly estimated taxes. Self-employment income: $[amount]. Other income: $[Y]. Deductions: [describe]. Include: federal + state estimates, safe harbor (100/110% prior year), penalty avoidance, quarterly payment schedule, automation setup.
Pro tip: Safe harbor: pay 100% prior year tax (110% if income >$150K) = no penalty regardless of this year's income. Simpler than estimating current year exactly.
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Advanced + Year-End
4 promptsHSA Triple-Tax-Advantage
13/16✨ What it does
ChatGPT maximizes HSA strategy from balance [X] and limit [Y], covering pre-tax deposits, invested growth, medical withdrawals, saved receipts, and after-65 use. Contribute the max, invest the cash, and store receipts for later tax-free withdrawals.
Maximize HSA tax strategy. Current HSA: $[X]. Contribution limit: $[Y]. Include: pre-tax contribution, investment growth tax-free, tax-free withdrawal for medical, pay medical out-of-pocket + save receipts, after 65 penalty-free for anything.
Pro tip: HSA = best retirement account. Triple tax advantage. Invest HSA + pay medical from cash + save receipts = tax-free withdrawals decades later. Better than 401k or Roth for medical-savvy savers.
529 College Savings Tax
14/16✨ What it does
ChatGPT plans 529 taxes for kids [ages] in state [X], covering state deductions, qualified expenses, leftover-to-Roth rules, and overfunding risk. Contribute what you can deduct, then avoid stuffing the plan past realistic tuition.
529 plan tax strategy. Kids: [ages]. State: [X]. Include: state tax deduction for contributions (varies by state), federal tax-free growth, qualified education expenses, Secure Act 2.0 leftover → Roth IRA conversion, overfunding risk.
Pro tip: 529 Secure Act 2.0: unused funds (up to $35K lifetime) can roll to Roth IRA for beneficiary. Removes over-funding risk. Makes 529 more flexible than ever.
Year-End Tax Moves
15/16✨ What it does
ChatGPT writes a December tax checklist for situation [describe], covering 401k, HSA, FSA, harvesting, charity, estimates, Roth conversions, RMDs, and bunching. Do the irreversible moves before December 31, then file the paperwork in January.
December tax move checklist. Current situation: [describe]. Include: max 401k, HSA, FSA, tax-loss harvesting, charitable giving, estimated tax true-up, Roth conversions before year-end, required minimum distributions if 73+, bunching strategies.
Pro tip: December tax moves = last chance for current-year impact. RMDs mandatory by Dec 31 (50% penalty if missed!). Roth conversions, charitable giving, harvesting all deadline Dec 31.
IRMAA Medicare Premium Avoidance
16/16✨ What it does
ChatGPT maps IRMAA avoidance for MAGI [X] around the $103K/$206K thresholds, with the 2-year lookback, Roth timing, harvesting, and withdrawal order. Hold large Roth conversions until you model next year's Medicare premium.
Avoid Medicare IRMAA premium surcharges. Age 63+ planning. Current MAGI: $[X]. IRMAA thresholds: $103K single / $206K married. Include: 2-year lookback, timing Roth conversions before 63, tax-loss harvesting, sequencing withdrawals, specific threshold management.
Pro tip: IRMAA uses 2-year-old tax return. Age 63 planning = future 65 premiums. Each bracket jump = $1K-4K/year extra premiums. Worth strategic planning before 63.
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