10/21/2026
Before you pull the trigger on rolling over that 401k plan from your old employer into an IRA, pause.
That seemingly routine rollover can close the door on a tax strategy that you’ll only get one chance to evaluate.
This decision point often appears with long-tenured employees who’ve accumulated substantial company stock inside their employer-sponsored retirement plans.
When they retire or change jobs, they may roll the entire account into an IRA.
The rollover may simplify the account, but it can also cause you to lose the ability to use a potentially tax-friendly strategy called net unrealized appreciation, or NUA, on your company stock.
How NUA works:
Instead of rolling the shares into an IRA, the shares may be distributed into a taxable brokerage account.
• You’ll generally recognize ordinary income on the cost basis of the shares distributed from the plan.
• The appreciation that occurred inside the 401k plan is generally taxed at long-term capital-gains rates when the shares are eventually sold.
Consider this example Imagine you’re an employee with:
• $5 million of company stock inside your 401k plan
• A cost basis of $1 million
• Approximately $4 million of embedded appreciation
When you’re evaluating an NUA strategy, you’ll typically have two paths forward.
Path 1: Complete a routine rollover
There’s generally no immediate tax impact if the rollover is completed correctly, tax deferral continues and future distributions from the IRA are generally treated as ordinary income. However, NUA treatment on the employer shares would no longer be available.
Path 2: Consider an NUA strategy
You could move the company stock into a taxable account and recognize ordinary income on the cost basis. The embedded appreciation would generally be taxed at long-term capital-gains rates when the shares are sold and the remaining retirement plan assets that aren’t employer stock can generally be rolled into an IRA as part of the distribution.
The difference between ordinary income and capital-gains tax rates gets most of the attention, but an NUA analysis should go much deeper.
• Can your cash flow absorb the ordinary income tax generated by the stock’s cost basis?
• How do current ordinary income rates compare with the rates you’d expect in the future?
• How quickly do you need to reduce your company-stock concentration?
• How could it affect your estate-planning goals? Charitable giving can be impacted too!
Most rollovers are treated as account-consolidation decisions. Employer stock can turn the rollover process into a one-time tax decision as well.
NUA isn’t appropriate in every case - the important thing is evaluating it while the option still exists, rather than discovering after the rollover that the decision can no longer be revisited or reversed.
If your 401k plan holds company stock, do you know its market value and cost basis?