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Taxes · plain-English guide

Realize gains while keeping the money invested

Use Tax Planning to test realizing selected brokerage gains now, raising basis for later withdrawals.

2 min readWorked example included
How to read itGain harvesting
Core relationshipnew cost basis = previous cost basis + gain harvested, limited by the account’s embedded gain

Conceptual illustration. The annual engine resolves the connected taxes and cash flows described below.

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The basics

Gain harvesting models selling appreciated holdings and reinvesting the proceeds. The account stays invested, while the gain becomes taxable income and its cost basis rises.

In Tax Planning, choose the participating accounts, active years, target capital-gains bracket, and any annual cap or income guardrail.

Illustrative numbers

Raise basis without changing the holding’s value

Account value before harvesting$100,000

Cost basis before harvesting$60,000

Gain realized$10,000

Basis after harvesting$70,000

Before any tax-funding withdrawals, the account is still worth $100,000. It now has $30,000 of embedded gain instead of $40,000.

Calculation transparency

How it works in MoneyWhatIf

  1. 01

    Step 2 of Tax Planning normally includes the realized Roth-conversion schedule from Step 1. Ordinary income already used by conversions reduces the room available for gains.

  2. 02

    The search stops at the selected gains bracket and applicable enabled guardrails. The optional NIIT guardrail applies only when selected; do not assume it is always active.

  3. 03

    Only chosen eligible accounts have their basis raised. The amount is limited by their embedded gains and by the strategy’s window and cap.

  4. 04

    The year-by-year explanation reports why a year harvested or did not harvest. Compare the overall funded outcome, including tax, cash needs, and later withdrawals.

Keep in mind

Model limits

This is a planning transaction; it does not send trades to a brokerage or choose security lots.

A favorable federal bracket alone does not prove a strategy helps. Review state tax, NIIT, marketplace coverage, and the later IRMAA effect.

This explanation documents the planning model. It is educational, not individualized tax, legal, Medicare, or investment advice.

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