What Should You Do If Your Investments Fall After You Complete a Roth Conversion?

Ross Marino |

You completed a Roth conversion after considering the tax cost and the role that money would play in retirement. Then the investments fell. Looking at the smaller balance, you may feel that you suffered two setbacks: an investment loss and a tax bill based on money that is no longer there.

That disappointment deserves attention. The useful response begins by separating the completed transaction from the choices you can still make. A lower balance may change what your household needs next, even though it does not rewrite the conversion.

What did the completed conversion establish?

For a direct conversion of investments from a traditional IRA to a Roth IRA, the value transferred establishes the gross conversion amount. The relevant value is the value when converted, not a later account balance. The custodian reports the transaction; a genuine valuation or processing error warrants prompt review and correction. A subsequent market decline is a different event.[1]

The taxable portion generally enters income for the conversion year. Any after-tax IRA basis must be handled under the applicable allocation rules, so the gross amount and taxable amount are not necessarily identical. You cannot undo conversions made after 2017 through recharacterization. Waiting until filing time or moving investments again does not restore that option.[2]

Selling a losing investment inside the Roth IRA does not create a deductible capital loss on your personal return.[3] The loss is economically real, but it does not automatically produce a tax offset against the conversion.

Why might another transaction feel like the answer?

Selling everything can feel like ending the mistake. Converting more can feel like improving the average entry point. Refusing to sell until the balance returns can feel like refusing to lose. Each reaction makes the earlier balance the target, even though that number does not tell you what the investment should do for you now.

Research offers reasons to pause in both directions. A study of individual brokerage accounts found that the securities investors bought subsequently underperformed those they sold.[4] Separate research using Taiwan trading records documented investors’ greater willingness to sell winners than losers.[5] These historical findings do not predict your investments. They caution against assuming either more activity or waiting to break even is automatically sound.

Which decisions can still respond to the decline?

Read each row from left to right. The completed fact provides context; the paired decision identifies where a review can still help. “Already determined” assumes an accurately processed conversion, not an unresolved reporting error.

Already determined

Still adjustable

Completed conversion value

Later prices do not reset it.

Tax-payment funding

Protect cash needed for the bill.

Completed transaction treatment

No reversal through recharacterization.

Future conversion amount

Reassess any uncompleted plan.

Past market movement

It has already occurred.

Current investment fit

Match risk to today’s needs.

Start with the money for taxes. If you reserved cash and it remains available, the decline may not have disrupted funding for payments. If you expected to sell investments that have also fallen, paying the same bill may now consume more of those holdings. Review that shortfall before committing additional money to a conversion.

Federal income tax is paid during the year through withholding or estimated payments. A lower Roth balance does not cancel required payments or excuse late payment.[6] Have your tax professional update the payment calculation and any state obligations. If selling taxable investments would supply the cash, include the sale’s potential gains or losses in that review.[7]

Dovetail Principle: When Life Changes, the Plan Can Change Without Starting Over

You can acknowledge an unwelcome outcome without treating the whole retirement plan as broken. Preserve the parts that still serve your life, and adjust the changed parts specifically. Reviewing the decline should support the next decision, not defend the last one.

What adjustment would serve your household now?

Revisit when you expect to spend this money and how much investment risk you are willing and able to carry. Those are different questions: you might feel comfortable with volatility while having less capacity for another loss because a necessary expense is approaching.[8] A longer horizon does not guarantee recovery, and a Roth account does not make an unsuitable investment suitable.

Ask your advisor whether the current allocation still fits across the household’s accounts. If it does, keeping it may remain reasonable. If the decline exposes excessive concentration or a spending mismatch, a measured change may be warranted. Neither conclusion requires waiting for the conversion-date balance to return.

Treat any remaining conversion plan as a new decision using current income, available tax money, and the purpose of the Roth assets. You may reduce, defer, or retain that planned amount. Converting more solely to make up a loss does not repair the earlier transaction.

Finish with a bounded decision: can the household still fund its taxes and sustain the investment plan? If yes, avoid forcing a repair. If something material changed, identify that change with your financial and tax professionals and adjust only the decisions that now need it.

For the payment decision that may need attention first, read How Do You Pay Taxes After the Paycheck Stops?.

About the author

Ross Marino, CFP®, CeFT®, is the Founder & CEO of Dovetail Financial and creator of Human-First Financial Guidance®. He helps people nearing or living in retirement connect their lives and wealth so that financial decisions become clearer, more personal, and easier to navigate.

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Notes

  1. Instructions for Forms 1099-R and 5498 (2026), Internal Revenue Service.
  2. Publication 590-A (2025), Contributions to Individual Retirement Arrangements (IRAs), Internal Revenue Service.
  3. Asset Allocation and Diversification, FINRA.
  4. Do Investors Trade Too Much? (1999), Terrance Odean, American Economic Review.
  5. Is the Aggregate Investor Reluctant to Realise Losses? Evidence from Taiwan (2007), Brad M. Barber, Yi-Tsung Lee, Yu-Jane Liu, and Terrance Odean, European Financial Management.
  6. Underpayment of Estimated Tax by Individuals Penalty, Internal Revenue Service.
  7. Capital Gains Explained, FINRA.
  8. Risk, FINRA.

Disclosure

This content is provided by Dovetail Financial Group LLC (“Dovetail Financial”) for informational and educational purposes only. It is not intended as, and should not be construed as, individualized investment, tax, legal, or accounting advice; a recommendation to buy or sell any security; or a recommendation to adopt any investment strategy. Because each person’s situation is unique, readers should consult their own financial, tax, and legal professionals before taking action based on this content. Information contained herein is believed to be reliable, but its accuracy or completeness is not guaranteed. Any opinions expressed are current as of the date of publication and are subject to change without notice. All investing involves risk, including the possible loss of principal. Asset allocation and diversification do not guarantee profits or protect against losses in declining markets. Past performance is not a guarantee of future results. Dovetail Financial Group LLC is a registered investment adviser. Registration does not imply a certain level of skill or training. Additional information about Dovetail Financial Group LLC, including Form ADV Part 2A and Form CRS, is available at adviserinfo.sec.gov. © 2026 Dovetail Financial Group LLC. All rights reserved.