Tax and financial advice from the Silicon Valley expert.

Developments and planning ideas for Roth IRA and Regular IRA accounts

Very high-income taxpayers should probably accelerate donations to 2025

Not all of the tax law changes in the One Big Beautiful Bill Act (OBBBA) enacted July 4, 2025 favor high-income taxpayers.

For example, effective for tax years beginning after 2025, under Section 70425 of the Act, the charitable contributions tax deduction for individuals is reduced by 0.5% of the taxpayer’s contribution base for the taxable year.

The contribution base is the taxpayer’s adjusted gross income, computed without regard to any net operating loss carryback to the taxable year.

For most taxpayers, this reduction might not seem significant. For example, if John has adjusted gross income of $1,000,000, the reduction would be $5,000.

Taxpayers with much higher income are hit harder. For example, if Jane has adjusted gross income of $20 million, the reduction would be $100,000. Jane would be in the 37% marginal federal income tax bracket plus 3.8% for the net investment income tax, or 40.8%, so this tax law change could increase Jane’s federal income tax liability by $40,800 for 2026 compared to 2025. If Jane makes $100,000 of charitable contributions each year, she should consider accelerating the contributions she would normally make during 2026 to 2025.

Charitable contributions disallowed because of the 0.5% of contribution base reduction are added to the charitable contributions carryover amount that might be deductible during the 5 subsequent tax years. They are only added to the charitable contributions carryover if the deduction ceiling amount is exceeded, such as 60% of the contribution base for cash contributions to qualifying charities. Otherwise, the deduction for the disallowed charitable contributions are lost. In the example above, if Jane made $100,000 of charitable contributions for 2026, the 60% limitation would be $12 million, so the tax deduction for $100,000 would not be added to the charitable contributions carryover and would be lost.

Another OBBBA change effective after 2025 reduces the tax benefit of itemized deductions by 2/37 (about 5.4%) of the lesser of (1) itemized deductions before the “haircut”, or (2) the taxable income of the the taxpayer, before itemized deductions, that exceeds the threshold for the 37% tax bracket. Note this “haircut” applies to itemized deductions after the 0.5% reduction of charitable contributions.

For example, Jane has taxable income for 2026, before itemized deductions, of $20 million, and itemized deductions before the “haircut” of $1,000,000. The 2026 threshold for the 37% tax bracket for a single person is $640,600. The taxable income, before itemized deductions, exceeding the threshold is $20 million – $640,600 = $19,359,400. The “haircut” would be $1,000,000 X 2/37 = $54,054.

Note that taxpayers age 70 1/2 or older may make qualified charitable distributions (QCDs) from a traditional IRA of up to $108,000 for 2025 and $111,000 for 2026. QCDs aren’t taxable and aren’t subject to the contribution base limits that apply for other charitable contributions. QCDs also “count” for satisfying required minimum distribution (RMD) requirements for traditional IRAs that currently apply for taxpayers who reached age 73 during 2025 or the ages when RMDs applied for earlier years.

Taxpayers who haven’t decided where to donate their charitable contributions yet can “park” the funds in a donor advised fund, community foundation or a private foundation. Lower maximum deduction thresholds might apply.

The 0.5% reduction of the charitable contributions deduction and the 2/37 “haircut” of itemized deductions are only two of the significant changes in OBBBA that are making tax planning more complicated, with many different effective dates and thresholds. Taxpayers should consult with tax advisors who work with tax planning software that incorporates these changes and understand the rules for charitable planning.

Stock Market’s Down! Convert to Roth Now?

The weak stock market might be an opportunity for taxpayers who want to convert their taxable traditional retirement accounts to tax-free Roth accounts.

On Monday, April 21, 2025, the S&P 500 sank 2.4%. The index at the center of many 401(k) accounts has retreated 16% below its record set two months ago.

The other stock market indexes, bond prices (including U.S. Treasury bonds) and the dollar have also fallen.

Reasons for the market weakness might be uncertainty as a result of President Trump’s imposition of tariffs of 145% to 245% on imports from China, broad-based 10% tariffs on other imports, and more tariffs on imports from other countries after a 90-day pause, together with his threat to fire Federal Reserve Chair Jerome Powell. Firing Chairman Powell threatens the independence of the Federal Reserve, which helps stabilize world financial markets.

With securities prices down, this could be a great time to make a Roth conversion.

What if securities prices fall even more? Timing financial decisions is problematic. Securities prices could fall even more if Trump actually fires Chairman Powell and goes ahead with many of Trump’s proposed tariffs that have been “paused.” Securities prices could improve if Trump reconsiders these threats and proposals and decides to not go ahead with them. Or, something else could happen. We just don’t know what will happen in the future.

We do know prices have already fallen, creating a potential opportunity to save taxes with a Roth conversion.

Why make a Roth conversion?

  1. After a short waiting period, most earnings and appreciation inside a Roth account are tax-free. . The earnings and appreciation inside a traditional retirement account are tax-deferred until distributions are made. (There is an exception for “unrelated business taxable income” that doesn’t apply to most taxpayers.)

2. Distributions from a Roth account after age 59 1/2 are tax-free, and so are many distributions before age 59 1/2. Distributions from a traditional retirement account in excess of any non-deductible contributions are generally taxable.

3. There are no required minimum distributions for a Roth account during the lifetime of the account owner (unless the retirement plan specifies otherwise.) Required minimum distributions generally must be made from a traditional retirement account when the account owner reaches the “applicable age”, currently age 73.

4. When the account owner dies after the required beginning date (April 1 of the year after reaching the “applicable age”), required minimum distributions must be made to the beneficiaries of a traditional retirement account. Since there is no required beginning date for Roth accounts (except Designated Roth Accounts of some employer plans), required minimum distributions don’t apply for most inherited Roth accounts. (Inherited Designated Roth Accounts can be rolled over to beneficiary Roth IRA accounts to avoid having to make required minimum distributions.) (Both traditional and Roth retirement accounts are subject to the requirement to be distributed by the end of the tenth year after the death of the account owner, with some exceptions.)

5. Distributions to beneficiaries from inherited Roth accounts are generally tax-free. Distributions to beneficiaries from inherited traditional retirement accounts are generally taxable, except for the recovery of any nondeductible contributions.

Since required minimum distributions don’t qualify for Roth conversions, taxpayers who have reached their required beginning date MUST TAKE THEIR REQUIRED MINIMUM DISTRIBUTION FOR THE YEAR BEFORE MAKING A ROTH CONVERSION.

A Roth conversion is currently taxable. Planning to have the cash available to pay the income taxes relating to the conversion is critical. You might want to consult with a tax consultant or financial planner to estimate in advance what the tax will be and decide how much to convert.

There can be other “side effects” of a conversion. For example, the additional income can reduce itemized deductions for medical expenses and can result in higher Medicare premiums. Get advice to “look before you leap.”

Now that tax return filing season is over, it’s tax planning season. Whether to make a Roth conversion during 2025 should be a topic on the agenda for a tax planning meeting for everyone who has a traditional retirement account.

Should a surviving spouse roll over an inherited retirement account?

When someone passes away is one time it's essential to consult with an estate planning lawyer, a tax advisor like a CPA or enrolled agent, and possibly a financial planner.

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Final regulations issued for Required Minimum Distributions

The IRS has issued final regulations (TD 1001) and proposed regulations (REG-103529-23) relating to Required Minimum Distributions from traditional and Roth qualified retirement plans, including Section 401(k) plans, and IRAs.

The regulations explain the rules for required minimum distributions under the SECURE Act of 2019 and SECURE 2.0 Act of 2022.

The final regulations are mostly the same as previously-issued proposed regulations with some minor changes in response to comments received by the IRS.

Notably, the final regulations didn’t change a controversial rule in previously-issued proposed regulations requiring that distributions be made annually when the plan participant dies after the required beginning date and annual required minimum distributions already applied during their lifetime. (This rule doesn’t apply to Roth account participants, because there is no required beginning date during their lifetimes.)

In most cases, that means when a plan participant dies after the required beginning date and annual required minimum distributions already applied during their lifetime, life expectancy distributions continue for the next nine years and the balance of the account is distributed during the tenth year after death. See your tax advisor for exceptions for “eligible designated beneficiaries” (including the surviving spouse) and non-designated beneficiaries.

See your tax advisor about how the new regulations apply for you and your family.

California FTB follows IRS with November 16 due date as California storm relief

The California Franchise Tax Board announced the evening of October 16, 2023 it is following the IRS by adopting a November 16, 2023 due date for 2022 income tax returns and payments for taxpayers who previously qualified for the October 16, 2023 due date. The relief applies to 55 of 58 California counties.

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At the last minute, IRS further extends 2022 filing and payment date for California storm victims

For residents of 55 of California's 58 counties that previously qualified for extended filing relief, the IRS has announced TODAY the tax-filing and tax-payment deadline has been further extended to November 16, 2023.

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Roth requirement for 401(k) catch-up contributions postponed

The IRS has announced a two-year administrative transition period for catch-up contributions to a qualified retirement plan (including a Section 401(k) plan) by highly compensated employees, permitting them to continue to be made on a pre-tax basis for taxable years beginning before January 1, 2026.

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Age 72 during 2023? You might get an extra IRA rollover

If you received a scheduled required minimum distribution from an IRA because you reached age 72 this year, the IRS just gave you a "mulligan". (This relief also applies for a surviving spouse.) The IRS has announced you may roll the distribution back to the account no later than September 30, 2023.

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Tax and financial advice from the Silicon Valley expert.