Rollover

The Direct Rollover — Trustee to Trustee

A direct rollover — also called a trustee-to-trustee transfer — is the movement of assets directly from the sending institution to the receiving institution without the account holder ever taking constructive receipt of the funds. The account holder instructs the distributing plan or IRA custodian to transfer the funds to the new plan or IRA custodian. The check is made payable to the new institution for the benefit of the account holder — not to the account holder personally — and is sent directly to the new custodian or forwarded by the account holder to the new custodian without being deposited into a personal account.

Because the account holder never receives the funds, the direct rollover is not a taxable distribution. No income tax is triggered. No withholding is applied. The sixty-day deadline does not apply because there is no distribution to complete. There is no limit on the number of direct rollovers an individual may execute in any twelve-month period — direct rollovers may be conducted as frequently as needed without limit. IRS Form 1099-R is issued by the distributing institution reporting the distribution with a distribution code indicating the direct rollover, and the account holder reports the rollover on their federal income tax return using Form 1040 with an offsetting rollover notation that eliminates the taxable income inclusion.

The direct rollover is the preferred method for virtually every rollover transaction because it eliminates all of the risks and complications associated with indirect rollovers. It is particularly important when rolling over assets from an employer-sponsored plan such as a 401(k) or 403(b), where the withholding rules for indirect rollovers are most consequential.

The Indirect Rollover — The Sixty-Day Rule

An indirect rollover — also called a sixty-day rollover — occurs when the distributing institution issues the funds directly to the account holder, who then has sixty calendar days to deposit the full amount into another eligible retirement account to preserve the tax-deferred status of the distribution. If the full amount is deposited within sixty days, the distribution is treated as a rollover rather than a taxable distribution and no income tax or penalty is owed.

If the account holder fails to deposit the full amount within sixty days — whether because they spent the funds, missed the deadline, or chose not to complete the rollover — the entire distributed amount that was not redeposited becomes taxable income in the year of the distribution. If the account holder was under age fifty-nine and a half at the time of the distribution, the additional ten percent early withdrawal penalty under IRC Section 72(t) applies to the taxable amount in addition to ordinary income tax.

The IRS may waive the sixty-day deadline in cases of financial institution error, severe illness, natural disaster, or other circumstances beyond the account holder's control — but waivers are granted only in limited circumstances and require a formal waiver application or a private letter ruling from the IRS. The account holder cannot simply claim that they intended to complete the rollover but forgot — the sixty-day deadline is strictly enforced except in the enumerated hardship categories.

The Mandatory Twenty Percent Withholding — The Critical Trap

The most examination-critical feature of indirect rollovers from employer-sponsored qualified plans — 401(k), 403(b), 457(b), and other employer plans — is the mandatory twenty percent federal income tax withholding that applies to all eligible rollover distributions paid directly to the account holder.

Under IRC Section 3405(c), when an employer plan makes an eligible rollover distribution directly to a participant — the indirect rollover scenario — the plan is legally required to withhold twenty percent of the taxable amount for federal income taxes. This withholding is mandatory — the participant cannot opt out, cannot elect a lower withholding rate, and cannot instruct the plan to skip the withholding even if they fully intend to complete the rollover within sixty days. The plan issues a check for eighty percent of the distribution and remits the twenty percent withholding to the IRS.

The withholding creates a critical practical problem. To complete the rollover and preserve the tax-deferred status of the entire distribution, the account holder must deposit one hundred percent of the original distribution amount into the new retirement account within sixty days — including the twenty percent that was withheld and sent to the IRS. The account holder must therefore make up the twenty percent withholding from their own personal funds outside the retirement account to deposit the full amount.

A worked example illustrates the mechanics precisely. An employee leaves their job with an eighty-thousand-dollar 401(k) balance and requests a distribution paid to themselves rather than requesting a direct rollover. The plan administrator withholds sixteen thousand dollars — twenty percent of eighty thousand — and issues a check for sixty-four thousand dollars. To complete a tax-free rollover of the entire eighty-thousand-dollar distribution, the employee must deposit eighty thousand dollars into the new IRA within sixty days — meaning they must come up with sixteen thousand dollars from personal funds to supplement the sixty-four-thousand-dollar check. If they deposit only the sixty-four thousand dollars received, the sixteen thousand dollars of withheld amount is treated as a taxable distribution — subject to income tax and potentially the ten percent early withdrawal penalty.

The withheld twenty percent is credited against the account holder's federal income tax liability for the year — so it is not permanently lost if the rollover is not completed or if only a partial rollover is completed. But it is a significant cash flow burden that many account holders do not anticipate, and it is the primary reason the direct rollover is strongly preferred for 401(k) rollovers.

The mandatory twenty percent withholding applies specifically to employer plan distributions. It does not apply to IRA distributions, which are subject to the more flexible ten percent default withholding rate that the account holder may change or elect to waive entirely by submitting Form W-4R to the IRA custodian.

The One-Rollover-Per-Year Limitation on IRA Indirect Rollovers

IRC Section 408(d)(3)(B) limits an individual to one IRA-to-IRA indirect rollover per twelve-month period across all of their IRA accounts combined. The Tax Court's ruling in Bobrow v. Commissioner — T.C. Memo 2014-21 — held in January 2014 that the one-rollover-per-year limitation applies on an aggregate basis across all of an individual's IRAs rather than on a per-IRA basis, consistent with the IRS's longstanding but previously disputed interpretation. The IRS subsequently issued Announcement 2014-15 and Announcement 2014-32 confirming that the aggregate one-rollover-per-year rule would be enforced beginning January 1, 2015.

The practical implication is that an individual who completes an indirect IRA-to-IRA rollover in any twelve-month period cannot complete another indirect IRA-to-IRA rollover until twelve months have elapsed from the date of the first distribution — regardless of how many separate IRA accounts they maintain. If they attempt a second indirect rollover within the twelve-month window, the second distribution is a taxable distribution and cannot be treated as a rollover.

The one-rollover-per-year limitation applies only to indirect IRA-to-IRA rollovers — it does not apply to direct trustee-to-trustee transfers between IRA accounts, which remain unlimited. It also does not apply to rollovers from employer plans to IRAs — an individual can complete unlimited direct rollovers from 401(k) accounts to IRAs regardless of how many IRA-to-IRA indirect rollovers they have recently completed.

Roth Conversions — A Related But Distinct Transaction

A Roth conversion is a specific type of rollover in which pre-tax funds from a traditional IRA, SEP IRA, SIMPLE IRA, or employer plan are moved to a Roth IRA. Unlike standard rollovers that preserve the existing tax treatment of the funds, a Roth conversion is always a taxable event — the converted amount is included in the account holder's gross income in the year of the conversion at their applicable marginal tax rate.

The taxability of Roth conversions arises from the fundamental difference between traditional and Roth account tax treatment — traditional accounts hold pre-tax funds that have not yet been subjected to income tax, while Roth accounts hold after-tax funds that will grow and be distributed tax-free. Moving funds from the pre-tax environment to the after-tax environment triggers the income tax that was deferred at the time of the original contribution.

The Roth conversion does not trigger the ten percent early withdrawal penalty even if the account holder is under age fifty-nine and a half — the conversion itself is not treated as a distribution for penalty purposes, only for income inclusion purposes. However, a five-year holding period applies separately to Roth conversions before the converted amounts can be withdrawn tax and penalty-free, distinct from the five-year holding period applicable to Roth IRA contributions.

Portability Rules — Which Accounts Can Roll to Which

The rollover portability rules govern which account types may receive rollover assets from which other account types, and understanding the permitted rollover directions is directly tested on Series 65 examinations.

Traditional IRAs may receive rollover assets from qualified plans including 401(k), 403(b), and governmental 457(b) plans, from SIMPLE IRAs after two years of participation, and from other traditional IRAs. Traditional IRA assets may be rolled to another traditional IRA, to a qualified plan that accepts incoming rollovers, or to a Roth IRA in a taxable conversion.

Roth IRAs may receive Roth 401(k) assets in a direct rollover, traditional pre-tax assets in a taxable Roth conversion, and assets from other Roth IRAs. Roth IRA assets cannot be rolled back to employer plans.

SIMPLE IRA assets may not be rolled to another IRA or qualified plan during the first two years of SIMPLE IRA participation — they may only be transferred to another SIMPLE IRA. After two years, SIMPLE IRA assets may be rolled to any traditional IRA, qualified plan, or 403(b) plan.

Examination Relevance and Key Takeaways

Rollovers are tested on the Series 65 examination in the context of retirement account portability, the direct versus indirect rollover distinction, mandatory withholding, the sixty-day rule, and the one-rollover-per-year limitation.

The key points to retain are these.

A rollover is the transfer of assets from one tax-advantaged retirement account to another in a manner that preserves tax-deferred or tax-free status. A direct rollover — trustee-to-trustee — transfers funds directly between institutions without the account holder taking receipt, triggering no withholding, no sixty-day deadline, and no limit on frequency. An indirect rollover distributes funds to the account holder who must redeposit the full amount within sixty calendar days to avoid taxation — failing to meet the sixty-day deadline renders the full undreposited amount taxable as ordinary income plus the ten percent early withdrawal penalty under IRC Section 72(t) if the account holder is under age fifty-nine and a half.

Employer plan indirect rollovers are subject to mandatory twenty percent federal income tax withholding under IRC Section 3405(c) — the account holder receives only eighty percent of the distribution and must fund the twenty percent gap from personal funds to deposit the full amount and complete the rollover. IRA indirect rollovers are subject to a default ten percent withholding that may be changed or waived using Form W-4R. The one-rollover-per-year limitation under IRC Section 408(d)(3)(B) — as interpreted in Bobrow v. Commissioner and confirmed by IRS Announcements 2014-15 and 2014-32 — restricts individuals to one IRA-to-IRA indirect rollover per twelve-month period across all IRA accounts combined — the limitation does not apply to direct trustee-to-trustee transfers or to rollovers from employer plans to IRAs. A Roth conversion is always a taxable event regardless of the rollover method — the converted pre-tax amount is included in gross income in the year of conversion at the applicable marginal tax rate.