The decision you make once, and cannot make again.
If you hold employer stock inside your 401(k), you have a tax election available at retirement that disappears the moment you roll the account to an IRA. There is no amended return that brings it back. Model both paths before you sign the rollover paperwork.
Distribute the shares in kind, pay ordinary tax on the cost basis now, and let the built-in gain be taxed at long-term capital-gains rates.
Roll the entire balance into an IRA; nothing is taxed until you withdraw, and then every dollar comes out as ordinary income.
See how each number was calculated
| Stock value today | $800,000 |
| Cost basis | $120,000 |
| NUA locked at distribution value minus basis, fixed on the distribution date | $680,000 |
| Value in 12 years | $1,609,757 |
| NUA election | |
| Less: LTCG tax on the NUA NUA × 20%, no NIIT | −$136,000 |
| Less: tax on post-distribution appreciation appreciation × 23.8% | −$192,722 |
| Less: ordinary tax on basis, paid now from other funds, and the growth it forgoes $42,000 grown at 6% for 12 years | −$84,512 |
| After-tax proceeds — NUA election | $1,196,523 |
| Roll everything to an IRA | |
| Less: ordinary income tax on withdrawal full value × 24% | −$386,342 |
| After-tax proceeds — IRA rollover | $1,223,415 |
What this model does not do
- Assumes you qualify — separation from service, disability, death, or age 59½, plus a full lump-sum distribution of the entire plan balance within one calendar year.
- Assumes the tax on basis is paid from other savings, and charges that money the same growth rate it would have earned.
- Uses one flat rate per category. Real brackets are graduated, and a large basis can push you up a bracket in the distribution year.
- Ignores state income tax, which can reverse the answer — particularly if you are moving between states in retirement.
- Does not model dying while holding the shares. NUA is income in respect of a decedent and receives no step-up; appreciation after the distribution does.
- Does not account for concentration risk. Holding one stock to defer tax is a portfolio decision, not just a tax decision.
Get the real number for your plan.
Send us your plan statement and we'll run the same analysis with your actual basis, your bracket, and your state — and tell you plainly if a straight rollover is the better move.
Request a review →Important: This tool is educational and hypothetical. It is not tax, legal, or investment advice, and it does not constitute a recommendation to take or forgo any distribution. Results are illustrations based on assumptions you selected; they are not projections, guarantees, or predictions of actual results, and actual outcomes will differ. Tax treatment depends on your specific facts and on current law, which is subject to change. Consult your CPA and attorney before acting. Skyview Financial Group is a registered investment advisor; registration does not imply a certain level of skill or training.