By Kevin Luu, Co-Founder and Chief Learning Officer. Reviewed on 2026-09-30.
An IRA transfer moves money directly from one custodian to another, so you never touch it, nothing is withheld, and there is no limit on how many you do. A rollover (the 60-day kind) pays the money to you first, and you have 60 days to deposit it into another IRA or plan, or it becomes taxable. For a family in a top bracket, the direct route is almost always the right one, and the indirect rollover is the one that causes expensive mistakes.
The same logic applies when you leave a job with a 401(k) or 403(b): ask the old plan for a direct rollover, paid straight to the new plan or IRA, rather than a check made out to you.
The three ways money moves between retirement accounts
The IRS uses three terms, and the differences matter more than the words suggest (IRS, Rollovers of Retirement Plan and IRA Distributions):
| Trustee-to-trustee transfer | Direct rollover | Indirect (60-day) rollover | |
|---|---|---|---|
| Typical use | IRA to IRA, such as changing brokers | Old 401(k) or 403(b) to a new plan or an IRA | Any plan or IRA, when the money is paid to you |
| Who holds the money | Custodian to custodian | Plan pays the new plan or IRA on your behalf | You, for up to 60 days |
| Withholding | None | None | 20% mandatory from an employer plan; 10% from an IRA unless you elect out |
| Deadline | None | None | 60 days from the day you receive it |
| Frequency limit | Unlimited | Unlimited | One IRA-to-IRA rollover per 12 months |
The one-rollover-per-year rule applies only to IRA-to-IRA rollovers where you take possession of the money. It does not apply to trustee-to-trustee transfers or to rollovers from an employer plan into an IRA. Under IRS Publication 590-A, the limit counts all of your IRAs together, not each account separately (IRS Pub 590-A).
Why the 60-day rollover is costly at a $950k income
The trap is the 20% withholding. When a 401(k) pays the money to you, the plan must withhold 20% for federal tax, even if you plan to roll every dollar over. To avoid tax on the withheld part, you have to replace it from your own cash within 60 days. You get the withholding back as a credit when you file, but only months later.
Worked example: leaving one Bay Area employer for another
Assumptions (illustrative): a married couple in California filing jointly, $950,000 of combined W-2 income in 2026 (about $900,000 of taxable income after deductions, federal and California), both in their 40s. One spouse leaves a biotech employer with a $420,000 pre-tax 401(k) and requests a check instead of a direct rollover.
- The plan withholds 20%, or $84,000. The check is for $336,000.
- To roll over the full $420,000 within 60 days, the family must add $84,000 from savings. The $84,000 withheld is credited against their 2026 tax when they file next spring, as a larger refund or a smaller balance due.
- If they deposit only the $336,000, the missing $84,000 is treated as a taxable distribution.
What the shortfall can cost at their bracket:
- Federal income tax at the 37% rate (2026 MFJ taxable income over $768,700): about $31,080.
- 10% additional tax on early distributions, since neither spouse is 59½ and no exception applies: $8,400.
- California tax at the 11.3% bracket rate (2025 joint rate schedule, the latest published: taxable income from $891,542 to $1,485,906): about $9,492. Their taxable income stays under $1,000,000, so the extra 1% Behavioral Health Services Tax does not apply.
- California’s own 2.5% additional tax on early distributions (FTB Form 3805P, 2025): $2,100.
That is roughly $51,072 lost on a move that would have cost nothing as a direct rollover. Missing the 60-day deadline entirely would make the whole $420,000 taxable.
California and Washington: what changes
California taxes a failed rollover as ordinary income, with no special rate, up to 13.3% at the top (12.3% plus the 1% Behavioral Health Services Tax on taxable income over $1,000,000, per the FTB 2025 rate schedules). Before age 59½, California also adds its own 2.5% additional tax on top of the federal 10% unless an exception applies.
Washington has no individual income tax in 2026, and retirement accounts are exempt from its capital gains tax (WA DOR), so a botched rollover there costs the federal tax and penalty only. That is changing: Washington enacted a 9.9% income tax on individuals and joint filers with AGI over $1,000,000, effective January 1, 2028 (WA DOR, Income tax). How it will treat retirement distributions is still pending DOR guidance.
Where to send an old 401(k) if you use the backdoor Roth
This is the decision high-income families most often get wrong, and it has nothing to do with the 60 days. Most families at this income are above the 2026 Roth IRA phase-out ($242,000 to $252,000 MFJ), so they fund Roth IRAs through the backdoor: a $7,500 nondeductible traditional IRA contribution for 2026, then a conversion.
The conversion is taxed under the pro-rata rule. Form 8606 counts the combined December 31 value of all your traditional, SEP and SIMPLE IRAs; money inside a 401(k) is not counted (IRS, Instructions for Form 8606).
Continue the example. If the $420,000 goes into a rollover IRA and the spouse then converts a $7,500 backdoor contribution in the same year, only $7,500 of $427,500 is basis. About 1.75% of the conversion is tax-free, and roughly $7,368 of the $7,500 is taxable. Repeat that every year and the backdoor stops working.
The cleaner path is a direct rollover into the new employer’s 401(k), if the new plan accepts roll-ins. The IRA balance stays at zero and the backdoor keeps working. Leaving the money in the old plan does the same, though it is one more account to track.
If the old plan holds after-tax contributions (the money behind a mega backdoor Roth), IRS Notice 2014-54 lets you split one distribution: pre-tax dollars to a traditional IRA or plan, after-tax contributions to a Roth IRA (IRS Notice 2014-54). Ask the plan to show the split before it processes the request.
Decision checklist when you change jobs
- Request a direct rollover or trustee-to-trustee transfer. Do not accept a check made out to you.
- If a check is unavoidable, have it made payable to the new custodian “for the benefit of” you. That is still a direct rollover.
- If you use the backdoor Roth, roll pre-tax money into the new 401(k), not an IRA.
- Ask whether the old plan holds after-tax or Roth money, and route each piece to the right account.
- Set new beneficiary designations on any new account. A designation on the old plan does not carry over.
- Keep the distribution paperwork and the new custodian’s confirmation for your tax preparer.
Common mistakes
- Doing a second IRA-to-IRA rollover within 12 months. The second one is not a valid rollover. Moving IRAs custodian to custodian avoids the issue entirely; see our guide to transferring a Roth IRA to another broker.
- Forgetting the 20% replacement. The 60 days apply to the full distribution, not the net check.
- Rolling into an IRA in a backdoor year. Covered in detail in our piece on the pro-rata rule.
- Cashing out a small old account. At a 37% federal bracket plus the 10% additional tax and California tax, a $30,000 balance can lose roughly 60% to federal and California tax and penalties by the time the return is filed (only 20% is withheld up front, so the rest shows up as a balance due).
What to write down for your kids
A family with two job changes can end up with five or six retirement accounts at different custodians. Write one page: where each account is, why the money went where it did (for example, “rolled into the new 401(k) to keep the backdoor Roth clean”), and who the beneficiaries are. Your spouse needs it now, and your children will need it later. As Kevin Luu puts it: “Your kids don’t need to inherit your portfolio. They need to inherit your decision-making process.”
Frequently asked questions
Is there a time limit on a 401(k) rollover?
Only for the indirect kind. If the money is paid to you, you have 60 days from the day you receive it to deposit it into another plan or IRA. A direct rollover has no deadline because you never take possession. You can leave money in a former employer’s plan and roll it over later, subject to that plan’s rules.
Can I move a 403(b) to an IRA the same way?
Yes. A 403(b) follows the same rollover rules as a 401(k): a direct rollover avoids withholding and the 60-day clock, while a check paid to you triggers 20% mandatory withholding. The same backdoor Roth caution applies, so check whether your new employer’s plan accepts roll-ins before choosing an IRA.
Does an IRA transfer show up on my tax return?
A trustee-to-trustee transfer between IRAs is not a distribution, so there is nothing to report as income. Direct rollovers from employer plans are reported on Form 1099-R but are not taxable when completed correctly. Keep the confirmation statements so your preparer can match them.
Next step
Before you sign a distribution form from an old employer, list every IRA balance you will have on December 31 and decide where the money goes based on your backdoor Roth plans. If you want a second set of eyes on the full picture, our retirement and employee benefits and tax management work starts with the Tax & Wealth Assessment.
This is general education, and the right move depends on your family’s full picture.
Kevin has advised high-income W-2 tech and biotech families since 2015, and leads the education-first Age Five Family Office from Brea, California.
Connect on LinkedIn → · About KevinThis is part of how we approach Investment & Risk Management for high-income W-2 families at Bright Advisers.
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