Retirement
advanced · $50K - $100K
If you have employer stock in your 401(k), you can distribute it in-kind (not sell), pay ordinary income tax only on what you originally paid, and pay long-term capital gains on all appreciation.
Can save 20%+ in taxes.
Tax Benefit
Convert ordinary income to long-term capital gains
Requirements
- Employer stock in employer-sponsored retirement plan
- Triggering event (separation, age 59.5, disability)
- Lump-sum distribution of entire plan
- Stock has significant appreciation
How to Implement
- 1Calculate cost basis vs current value of employer stock
- 2Verify triggering event qualifies
- 3Distribute stock in-kind to taxable brokerage (not IRA)
- 4Pay ordinary tax on cost basis only
- 5Pay capital gains rate on NUA when sold
Frequently Asked Questions
Related retirement strategies
Sources
- Internal Revenue Service, Rev. Proc. 2025-32
2026 inflation-adjusted amounts (tax brackets, standard deduction, estate & gift, FSA, credits)
- Internal Revenue Service, Notice 2025-67
2026 retirement plan limits (401(k), IRA, SIMPLE, catch-up)
- Internal Revenue Service, Rev. Proc. 2025-19
2026 HSA and HDHP inflation-adjusted limits
Educational information only. Not financial, tax, or legal advice or a recommendation. Figures are drawn from the primary sources cited above; verify current amounts with the source before acting.