Estimate capital gains
The Capital Gains Estimator can help you plan your investment sales and see how they will affect your tax situation. You can see your gain or loss from potential sales, estimate your capital gains tax and after-tax net proceeds, and experiment with offsetting capital gains (Profit on the sale of stocks, bonds, mutual funds, or capital assets. Capital gains usually receive favorable tax treatment compared to other forms of income.) with capital losses.

For even more powerful capital gains estimation tools, import your Microsoft Money Plus Deluxe investment information file to GainsKeeper. GainsKeeper makes it simple for you to use your Money file to complete your IRS Schedule D, and offers precise capital gains calculations that automatically adjust for wash sales, stock splits, mergers, and spin-offs. In addition, you’ll have access to tools and suggestions that can help save money on your taxes. All Microsoft Money Plus Deluxe users receive a free 30-day trial for GainsKeeper and discounts on an annual subscription. Money Premium and Money Small Business users get a whole year free!

  1. Click Investing, click Investing Tools, and then click Capital Gains Estimator.
  2. Click Get Started.
  3. Enter the following information:
    • Select your filing status. Your filing status affects your income tax brackets. If you will file as a Qualifying Widow(er) with Dependent Child, select the Married Filing Jointly filing status.
    • Select your income bracket for this tax year. Money uses this to determine your short-term and long-term capital gains tax rates.
    • Do you want to estimate your state income tax on capital gains? If your state does not tax capital gains or you don’t want to consider state income tax in your capital gains tax projections, select No, don’t estimate state income tax on capital gains. Otherwise, select Yes, estimate state income tax on capital gains using these rates, and then enter the rates at which your state taxes short-term and long-term capital gains. If your state does not have special capital gains tax rates, enter the rate at which your ordinary income is taxed by your state.
    • In the Short-term loss or Long-term loss boxes, enter your capital loss carry-overs.
  4. Click Next.
  5. Select the accounts that contain investments you may want to sell, and then click Next.
  6. On the Plan sales of investments page, enter the following information about your proposed investment sale:
    • Date of sale: Enter today’s date or the future date when you expect to sell the investment. For example, if you have owned an investment for almost one year, you can enter a date at which you will have owned it for more than a year and see how qualifying for the long-term capital gains tax rate affects your tax.
    • Distribution method: If you sell less than all the shares you own of an investment that you purchased at different times, you can choose a distribution method to determine which lots you sell shares from. Unless you specify otherwise, the shares from the first lot you purchased will be the first shares assumed sold.
      • FIFO. Select First-In, First-Out (FIFO) if you want to sell the first shares you purchased. If your investment has been steadily gaining in price, this method will generally give you the largest taxable gain because you will be selling the stocks you purchased for a lower price.
      • LIFO. Select Last-In, First-Out (LIFO) if you want to sell the last shares you purchased.
      • Max gain. Select Max gain if you want Money to sell the shares with the lowest basis, resulting in the maximum gain this year. You may want to consider this strategy if you are in a lower tax bracket this year than usual, or if you have capital losses to offset your gains.
      • Min gain. Select Min gain if you want Money to sell the shares with the highest basis, resulting in the minimum gain this year.
      • Custom. Select Custom if you want to specify which shares from each lot to sell. Unless you use FIFO, you must tell your broker in writing which shares you want to sell before you make the sale.
    • In the Sale Price column, enter the price at which you expect to sell each investment. To use the current price, in the left pane, click Update prices, and then click Update prices online.
    • In the Qty to Sell column, enter the total number of shares you want to sell for each investment. The shares will be distributed by lot, according to the distribution method you selected at the top of the page. If you selected Custom, enter the number of shares you want to sell from each lot.

      Under Results of proposed sales, you can see the total amount you would receive from the sale, any carry-overs, your net gain or loss, estimated federal and state capital gains tax, and your after-tax net proceeds.

  7. Click Next.
  8. The Estimated Capital Gains Tax Summary shows the results of your proposed investment sales, your capital gains and estimated capital gains taxes on investment sales so far this year in your Money file, and the results of your proposed and year-to-date investment sales combined.
  9. To print the summary, click Print at the bottom of the page.


  • The Capital Gains Estimator is a tool in Money that helps you understand the tax consequences of potential or actual investment sales. GainsKeeper, a Microsoft partner, is a Web service that provides subscribers with detailed capital gains tracking, automated completion of IRS Schedule D, and tools and suggestions for managing capital gains and losses. You can use your Money investment information in GainsKeeper.
  • The Capital Gains Estimator excludes investments that are in retirement accounts because gains in retirement accounts are not taxable and losses are not deductible.
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Estimate capital gains