Fresh prompt pack

Tax Season Portfolio Review: 8 AI prompts for tax-aware portfolios

A pack for organizing tax-aware portfolio review questions before speaking with a qualified tax professional.

Added May 31, 2026 8 copy-ready prompts Library-matched

Copy-ready tax season portfolio review AI prompts

Tax Document Intake Checklist

Start here Beginner

Organizes the forms, statements, and transaction records needed before a portfolio tax review.

Taxes

ID 430

Create a tax document intake checklist for an investor. Include brokerage 1099s, dividend and interest forms, crypto 1099-DA if applicable, cost-basis reports, realized gains/losses, wash-sale notes, transfers, charitable donations, and questions for a qualified tax professional.

Brokerage 1099-B Reconciliation

Beginner

Helps users compare broker forms with their own trade records before filing.

Taxes

ID 431

Act as a tax-prep organizer, not a tax advisor. Help me reconcile my brokerage 1099-B with my own records. Check proceeds, cost basis, acquisition dates, holding periods, wash-sale adjustments, missing lots, and items to confirm with a tax professional.

Digital Asset 1099-DA Cross-Check

Beginner

Addresses the new digital asset reporting workflow and the risk of missing or incomplete basis data.

Compliance

ID 432

Help me review a Form 1099-DA for digital assets. Compare proceeds, transaction dates, transferred-in assets, missing or zero cost basis, wallet transfers, exchange records, and crypto tax software output. List issues to resolve before filing.

Cost Basis Gap Finder

Medium

Finds missing basis, transfers, splits, reinvestments, and records that can distort taxable gain calculations.

Taxes

ID 433

Review my investment records for cost-basis gaps. Look for transferred assets, reinvested dividends, partial sales, crypto wallet transfers, missing acquisition dates, inherited or gifted assets, and broker-reported basis that may not match my records.

Tax-Loss Harvesting Decision Aid

Medium

Structures a tax-loss harvesting review while keeping portfolio exposure and replacement risk visible.

Taxes

ID 434

Create a tax-loss harvesting decision aid for my portfolio portfolio summary. Identify loss candidates, replacement exposure ideas, timing issues, holding-period considerations, transaction costs, portfolio drift, and questions to ask a tax professional before acting.

Wash-Sale & Replacement Exposure Watch

Medium

Flags wash-sale and substantially similar exposure questions without giving legal conclusions.

Compliance

ID 435

Build a wash-sale and replacement exposure checklist for my trades trade list. Identify purchases before and after loss sales, similar ETFs or funds, retirement-account transactions, crypto edge cases, and items that require professional tax judgment.

Estimated Tax Cash Reserve Planner

Medium

Helps users set aside cash for potential tax liabilities from gains, dividends, interest, and crypto sales.

Taxes

ID 436

Create a tax cash-reserve planner for my realized gains, dividends, interest, and crypto sales tax summary. Estimate what data I need, separate short-term and long-term items, flag state-tax questions, and suggest a conservative cash reserve workflow to discuss with a tax professional.

Advisor Question Pack

Pro

Prepares concise questions for a CPA or tax advisor so the meeting is faster and more productive.

Regulations

ID 437

Create a question pack for meeting a CPA or tax advisor about my investment portfolio. Include questions about capital gains, losses, wash sales, ETF distributions, crypto 1099-DA, estimated taxes, recordkeeping, state tax, and documentation I should bring.

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