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    • Revocable Living Trust
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Tag Archives: Retirement Taxes

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  2. Entries tagged with "Retirement Taxes"

After-tax 401(k) contributions and associated earnings moving to Roth and traditional IRA accounts at retirement

What Happens to After-Tax 401(k) Money When You Retire?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Have after-tax contributions inside your 401(k)? Before rolling the whole account into an IRA, learn why pretax and after-tax dollars may deserve different destinations at retirement.

Traditional IRA converting to a Roth IRA beside an estate plan and family legacy symbol

Does a Roth Conversion Reduce Estate Taxes?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Does converting an IRA to Roth reduce estate taxes? Learn why Roth conversions can change the income-tax character of an inheritance without automatically removing assets from your taxable estate.

Comparing a Roth conversion with the NUA strategy for company stock held inside a 401(k)

Roth Conversion or NUA? What If Your 401(k) Holds Company Stock?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Have company stock inside your 401(k)? Before rolling everything to an IRA or Roth, compare Roth conversion planning with the special NUA tax rules that may apply to employer securities.

Comparing paying off a mortgage with using available cash for Roth conversion taxes

Pay Off Your Mortgage or Use the Cash for a Roth Conversion?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Have enough cash to pay off your mortgage before retirement? See why using that money for the house can change your Roth conversion strategy, liquidity, and long-term retirement math.

Sequence-of-returns risk and its effect on Roth conversion planning

How Does Sequence-of-Returns Risk Affect a Roth Conversion?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Retiring into a bad market? Learn how sequence-of-returns risk can change the way you think about Roth conversion amounts, taxes, cash reserves, and portfolio withdrawals.

Donor-advised fund and Roth conversion tax-planning strategies

Can a Donor-Advised Fund Help With Roth Conversion Taxes?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Planning a Roth conversion and significant charitable giving? Learn how a donor-advised fund may let you bunch donations into a conversion year and why the math still needs to be tested.

Tax-loss harvesting and its potential effect on taxes during a Roth conversion

Can Tax-Loss Harvesting Reduce the Taxes on a Roth Conversion?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Have investment losses and considering a Roth conversion? Learn what capital losses can offset, what they generally cannot, and how both strategies may fit together.

Comparing cash, brokerage, Traditional IRA, and Roth IRA withdrawals during Roth conversions

Which Accounts Should You Spend From While Doing Roth Conversions?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Doing Roth conversions after retirement? The account you use for living expenses can change your taxable income, conversion room, liquidity, and future retirement balances.

Roth conversion planning before deferred compensation payments begin

Should I Do Roth Conversions Before My Deferred Compensation Pays Out?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Retiring with deferred compensation, RSUs, or stock compensation still coming? See why future compensation income can change the best years for Roth conversions.

Roth conversion planning while preparing for potential long-term care costs

Should I Do a Roth Conversion If I’m Worried About Long-Term Care Costs?

IRA / 401(K) Roth Conversions, Retirement InsightsBy Dr. Dylan FosterSeptember 20, 2026Leave a comment

Worried that future long-term care costs could force large taxable IRA withdrawals? See how Roth conversion planning may create another source of retirement liquidity.

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