Now accepting new clients for the 2027 tax season.

Investment Income & Capital Gains Tax Preparation

Your investments deserve careful tax reporting.

Brokerage statements can run to dozens of pages, and the numbers that matter aren’t always the ones on top. We prepare your individual return with your investment income, sales, and losses reported accurately, including the details that affect how much tax you pay.

Check the States We Serve

What we prepare and report

  • Sales of stocks, bonds, mutual funds and ETFs from Form 1099-B, on Form 8949 and Schedule D.
  • Dividends and capital gain distributions from Form 1099-DIV, including qualified dividends taxed at capital-gain rates.
  • Interest income from Form 1099-INT and 1099-OID, including tax-exempt interest.
  • Capital loss carryforwards from prior years, applied and carried forward correctly.
  • Investment-related forms when they apply, such as foreign tax paid by your funds.

Common tax considerations

Short-term and long-term

Assets held for more than a year generally qualify for lower long-term capital gain rates; those held a year or less are taxed like ordinary income. Your 1099-B usually separates them, and we check that it’s right.

Cost basis

Your gain or loss depends on your basis: what you paid, adjusted for reinvested dividends and other events. Brokers report basis for most newer purchases, but not always for older shares or transferred accounts. Missing basis can mean paying tax on money that was never a gain.

Losses and carryforwards

Capital losses offset capital gains, and up to $3,000 of net loss a year ($1,500 if married filing separately) can offset other income. Anything beyond that carries forward to future years, so your prior-year return matters.

Wash sales

If you sold at a loss and bought the same or a substantially identical investment within 30 days, the loss may be disallowed for now and added to your new basis. Brokers report many of these; we look for the ones they can’t see across accounts.

Documents and records to gather

  • Consolidated 1099 from each brokerage
  • Forms 1099-B, 1099-DIV, 1099-INT, 1099-OID
  • Cost basis records for older or transferred shares
  • Last year’s return (for loss carryforwards)
  • Schedule K-1s from any partnerships or trusts
  • Corrected 1099s if your broker issued any
The Square Penny provides tax preparation, not investment advice. We report what happened in your accounts; we don’t recommend what to buy, sell, or hold.

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You receive a quote after we review your intake and documents.