How do I use the What Should I Sell component of the Capital Gains Estimator

Using the powerful What Should I Sell component of the Capital Gains Estimator, you can specify an amount, rank sales criteria such as maximize my after-tax gain, and then have Quicken search for an optimal combination of securities to meet your specified objectives.

1. From within the Capital Gains Estimator, choose What Should I Sell on the left navigation bar.

  • What happens now?
    The first time you use the Capital Gains Estimator, you'll be taken to the What Should I Sell page as you enter your information prior to proposing a sale. If you've previously entered proposed sales, launching the Capital Gains Estimator will take you to either:
    • The page you were on when you last visited the Estimator.
    • The What if Scenarios page (What If Scenario is selected on the left navigation bar).

2. As you work through the What Should I Sell page, you may need additional information. Click a topic below to learn more.

  • Update your portfolio to include recent market prices
    • From the Options drop-down menu, choose Update YTD Cap. Gains. Click Continue, and then click OK to update your year-to-date capital gains information from Quicken's Tax Planner.
    • From the Options drop-down menu, choose Get Online Quotes (Internet access required).
      • If you have incentive stock options, verify the fair market value
        If you have incentive stock options (ISO) and are converting from a previous version of Quicken, the fair market value of your options was not stored in the earlier version of Quicken at the time you entered them. What Should I Sell may make mistaken calculations concerning these options unless you now correctly enter the initial fair market value.
  • Tell Quicken how much money you want to make from this sale
    Enter, in dollars, the amount you want to receive in gross proceeds from this sale. Under some circumstances you might want this amount to be zero.
    • Set the cash amount to zero with a high ranking for Minimize taxes and commissions to yield a proposed loss sale that can offset other (including non-investment) tax liabilities.
    • Set the cash amount to zero and use the Balance my year-to-date capital gains goal to yield a proposed loss sale that will offset previous capital gains. (See Identify your goal for this sale below.)
  • Identify your goal for this sale
    A sales goal such as Maximize profits/gains consists of nine ranked objectives. Four common goals are predefined on the main What Should I Sell page. You can either choose one of these predefined goals or create a custom goal. To create a custom goal, select None of the above, expand the Custom Settings drop-down, and adjust the individual objectives to your liking. Click here to learn more about how What Should I Sell works with goals, objectives, and rankings.
  • Search
    Click Search to begin the What Should I Sell analysis. Quicken will review your data for a set of holdings to sell.
    • What happens now?
      The Search dialog appears and displays a progress bar. The progress bar is colored:
      • Yellow, when What Should I Sell is preparing to calculate your scenario
      • Blue, when What Should I Sell is looking for a solution
      • Green, when What Should I Sell has found a solution within your parameters
      • Red, if What Should I Sell couldn't find an acceptable solution

      The analysis is complete when the progress bar displays 100 percent.

  • Adjust your settings and perform an additional analysis (Optional)
    Settings determine the amount of time used for a search, the conditions under which Quicken should stop searching, and so on.

    You can't adjust settings while a search is in progress. Either wait until the current search has finished, or choose Stop to halt it. Then, choose Settings to modify:

    • The variance (from your target dollar amount) that you're willing to accept in your result. The default is ten percent.
    • A time limit for your search (default is 30 seconds)
    • The number of optimal solutions Quicken should seek before ending the search process (default is 5)
      • What is meant by the number of optimal solutions?
        What Should I Sell searches by performing multiple passes: it solves the problem once and then, as long as time remains, it attempts a better solution. This setting limits the number of passes (optimal solutions) independent of any specified time limit.
    • Whether the search should stop immediately after What Should I Sell finds an optimal result. If Stop as soon as the first acceptable answer is found is not checked, What Should I Sell will continue searching for the full time limit specified above.
    • Whether What Should I Sell will perform a quick or an exhaustive search. A quick search will try different searching methods and choose one best result. An exhaustive search can merge individual best-of-kind searches to obtain a final result.

3. Click OK to accept your settings. Then, in the Search dialog, click Start.

  • View your results
    Click View Results to dismiss the Search dialog. You will be taken to the Proposed Sales window on the Estimator page to view What Should I Sell recommendations. From here, you can manually fine-tune the results. You can also select a different scenario and rerun What Should I Sell for comparison.


  • If you have employee stock options, What Should I Sell will not recommend selling any underwater options, and underwater shares will not be included in the What Should I Sell analysis.
  • What Should I Sell assumes that all unexercised stock options will be treated as a same-day sale.
  • If you receive an incomplete Tax Plan message after clicking Search from within What Should I Sell, you should update your tax information to ensure accurate results. Carefully review the options in Step 2 of the Choose tax rates in the Capital Gains Estimator topic before proceeding (click each radio button to view the associated option).
  • If you're using What Should I Sell to evaluate whether U.S. savings bonds should be cashed in early, make sure you've entered the Savings Bond interest in the penalties field of the Transaction Fees dialog for the account from which you purchased the bond. For example if a U.S. Series I Savings Bond pays 5 percent interest, then cashing it in early would cost you the most recent 6 months interest (5 percent in this case).
  • To learn more about the model used by What Should I Sell, click here.

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