Planning tool

10b5-1 sale schedule and diversification planner.

This planner models a 10b5-1 trading plan schedule: choose what portion of your employer-stock position to sell, the sale cadence (monthly or quarterly), and the plan duration. It produces a period-by-period sale schedule and a year-by-year federal LTCG and NIIT tax estimate — so you can see how multi-year spreading compares to a compressed plan before you coordinate with your advisor, broker, and counsel.

Why the schedule structure matters

A 10b5-1 plan can be written as a fixed-share plan, a fixed-dollar plan, or a price-conditional plan. The sale structure affects execution mechanics but the same tax framework applies to all of them: each sale produces capital gain, gains in a given calendar year stack on top of ordinary income, and the 3.8% NIIT applies when modified AGI crosses $200,000 (single) or $250,000 (MFJ).¹

Multi-year spreading: the core tax planning question

For large employer-stock positions, the single most important decision is how many calendar years the gains spread across. A $3M position sold in one year can push gains deeply into the 20% bracket and fully into NIIT territory, producing a materially higher effective rate than spreading the same total gain over 24 or 36 months.

The planner above applies the same ordinary income estimate to each plan year. In practice, year-to-year income can shift — particularly if an executive retires, changes roles, or controls RSU vesting elections. The rough rule of thumb: if a year's gain alone is likely to push combined AGI above $583,750 (MFJ) or $518,900 (single) — the 2026 threshold where LTCG reaches 20% — spreading the plan over an additional year is worth modeling with your advisor.²

Constraints that can change the schedule

• Cooling-off period: Directors and officers generally cannot execute the first sale until 90 days after plan adoption (up to 120 days, the later of 90 days or two business days after the next earnings release for the quarter in which the plan was adopted). Non-officer employees have a 30-day waiting period. Full cooling-off period guide.³
• Single-plan rule: The 2022 SEC amendments generally prohibit having more than one single-counterparty 10b5-1 plan in effect at the same time (with a limited exception for plans established to sell shares to cover tax withholding on RSU vests). A new plan terminates any prior plan.³
• Rule 144 volume limits for affiliates: If you are an affiliate of your company (typically an officer, director, or 10%+ shareholder), Rule 144 volume limits apply to sales of control securities even inside a 10b5-1 plan. The ceiling is the greater of 1% of shares outstanding or the average weekly reported trading volume for the prior four weeks. Very large positions may not be fully saleable within one plan year even if the tax modeling supports a compressed schedule.⁴
• Section 16 reporting: Officers and directors report each disposition on Form 4 within two business days of the trade date. High-volume plans mean frequent Form 4 filings — your securities counsel typically handles this coordination.³
• IRMAA exposure: For executives within two years of Medicare eligibility (age 63+), a large sale year can raise Part B and D premiums for the following two years. 2026 IRMAA surcharges begin at $106,000 (single) or $212,000 (MFJ).⁵
• Plan modification and termination: A single modification to an existing plan — including changing the sale price, number of shares, or timing — can reset the cooling-off period and requalify the plan under SEC scrutiny. Terminating a plan prematurely also carries risk if the termination occurs while you possess MNPI.

For the full compliance picture, see the 10b5-1 plan rules overview, the pre-adoption checklist, and our plan structure examples.