The mechanics of the split, and the holding-period quirk. At distribution, you include the plan's cost basis in the shares as ordinary income. The appreciation above that basis is excluded. When you sell, that excluded amount is long-term capital gain no matter how briefly you held the shares after the distribution, which is a genuine exception to the normal one-year rule. Any further appreciation after the distribution is a separate matter and follows the ordinary holding-period rules, so gain accrued in the first year after the distribution is short-term. Form 1099-R reports the net unrealized appreciation in box 6, which is the number to look for when the plan sends its paperwork.
What counts as employer securities. Section 402(e)(4)(E) restricts "securities" to "only shares of stock and bonds or debentures issued by a corporation with interest coupons or in registered form," and defines securities of the employer corporation to include securities of a parent or subsidiary. So this works for actual company shares, not for a fund holding them, and not for a company that is not a corporation. The shares also have to be distributed in kind. If the plan sells them and hands you cash, there is no appreciation left to exclude.
The all-or-nothing conditions, and the opt-out. The distribution has to qualify as a lump-sum distribution under section 402(e)(4)(D), which means the entire balance in that kind of plan paid within one taxable year on a qualifying event. Partial approaches exist in practice, because you can distribute the employer stock in kind while rolling the rest of the balance over, but the underlying distribution still has to meet the statutory test. Running in the other direction, the statute permits you to decline the treatment: a taxpayer "may elect, on the return of tax on which a lump sum distribution is required to be included, not to have this subparagraph apply." Publication 575 spells out the consequence of that election, which is that the full value of the securities is taxed as ordinary income and no portion qualifies for capital gain treatment under these rules. Declining is occasionally sensible, for instance where the basis is high relative to the appreciation.
A narrower version of the benefit survives even without a lump-sum distribution. Section 402(e)(4)(A) and Publication 575 both provide that where the distribution is not a lump-sum distribution, tax is still deferred on the appreciation attributable to the participant's own after-tax contributions, just not on the far larger share attributable to employer contributions. That matters only to someone who made after-tax contributions to the plan, which is why the election is usually described as all or nothing.
The 10% additional tax reaches only the taxable part. Someone under 59½ without an applicable exception owes the additional tax on the ordinary-income cost basis, not on the excluded appreciation. That makes the cost of an early election smaller than it first appears, though separating from service at 55 or later from a qualified plan is a common way the exposure disappears entirely.
The estate-planning trap, which is the most expensive thing on this page. Inherited assets ordinarily receive a step-up in basis to fair market value at death. Net unrealized appreciation does not. The appreciation embedded at the time of distribution is treated as income in respect of a decedent, so an heir inherits it and pays capital gain tax on it when the shares are sold. Only the appreciation that accrued after the distribution receives a step-up. Anyone applying the general step-up rule to inherited employer stock that came out under this election will reach the wrong answer, and the error is easy to make because the shares sit in an ordinary brokerage account looking like any other holding.
The unglamorous risk is concentration. The election rewards a large gap between basis and market value, and that gap is produced by holding a lot of one company's stock for a long time, often the company that also pays your salary. The tax result and the concentration risk grow from the same root, and the tax tail should not be what decides how much of one company you own.