Sell your RSUs at vest, or hold?

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Compare the after-tax payout from selling at vest and reinvesting in the market versus holding the shares — across the LTCG cliff at 12 months.

Beta · invite-only · AlphaLatitude Inc. · Free Tools

Your vest

pre-IPO? enter price manually

Tax inputs

Hold strategy

1 yr
20%
20%
10.0%

Best after-tax payout — at year 1 yr

$47,709

Sell + invest wins by $4,981 over Hold 1 yr.

Estimates only. Not financial advice.

This vest pushes your top federal rate from 24% to 35%. Hover the Federal value below for the bracket-by-bracket slicing.

Heads-up: under-withholding. Your employer withholds federal tax at the IRS supplemental rate (22.0% on this vest, ≈ $17,600). Your marginal federal rate on this vest is 32.7%, owing $26,171. Expect to settle the $8,571 gap at tax time.

The hidden purchase

Tax was paid at vest either way. Holding is mathematically equivalent to taking $44,509 in after-tax cash and buying $44,509 of this stock today.

Most diversification frameworks would advise against a purchase that size in a single name; the right answer depends on your conviction in this stock. Holding past one year converts the gain to LTCG.

Sell + invest

Best payout
Vest value (shares × price)$80,000
Federal
State
Medicare−$1,160
Additional Medicare−$720
Market gain over 1 yr at 10.0%$4,451
Cap-gain tax on diversified gain — LTCG (federal + state + NIIT)−$1,251
Net at year 1 yr$47,709

Sell every share at vest; invest the after-tax cash at the market return for 1 yr, then liquidate. Diversified — no single-stock concentration risk.

Hold 1 yr

Vest value (shares × price)$80,000
Vest tax (federal + state + FICA)
Net at year 1 yr$42,728

Sold 444 shares to cover vest tax (net-settled); kept 556 shares 1 yr to qualify for long-term capital gains.

Social Security + Medicare are payroll taxes (collectively called FICA) — they apply because you're still employed at vest.

Both columns are stated in year-1 yr dollars. The sell side compounds at the market return; the hold side compounds at your single-stock expected return after a 20% volatility drag.

Estimates only. Assumes net-settled (sell-to-cover) vesting; double-trigger and pre-IPO RSUs are out of scope. Excludes multi-state moves, AMT interactions on other equity, and 83(b) elections. Not financial advice.

You evaluated one RSU vest. The beta plans every vest of every grant across years, with concentration and AMT in the loop.

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What this calculates

  • Tax taken at vest (federal, state, FICA, Medicare): locked in either way.
  • The withholding gap: what you'll owe at filing when your marginal rate is above the 22% supplemental rate your employer withholds.
  • Sell at vest and reinvest, vs. hold 12 months for the long-term capital-gains rate.
  • How far the share price has to move for that 12-month wait to actually pay off.

Models taxable single-trigger vests. Pre-IPO double-trigger RSUs are out of scope.

Read the deep dive: Five RSU mistakes that quietly grow your April tax bill →

Methodology

Optimization. Compares sell-at-vest vs hold-for-LTCG net payouts for an RSU vest across the 12-month short-term cliff, state tax, FICA, and your growth assumption — returns the dollar gap between the two paths. The search is deterministic: the same inputs return the same answer, so the recommendation is verifiable.

Tax-code coverage. Full federal code (ordinary brackets, long-term capital gains, AMT with credit recovery, FICA, Net Investment Income Tax) plus all 50 states and DC for state ordinary brackets and LTCG treatment. State AMT modeled for CA, CO, CT, MN. Brackets reflect IRS Rev. Proc. 2025-32 and the One Big Beautiful Bill Act (OBBBA) provisions for tax year 2026. Validated against 870+ unit tests covering bracket math, AMT credit recovery, state conformity, and the optimizer's search path.

Why use an optimizer rather than asking an LLM to do the math: a benchmark of five frontier large language models on the same multi-year ISO problem found that all 15 trials overshot the achievable after-tax outcome by 2x to 20x (HackerNoon write-up).

AI assistant integration

Use this from Claude, Cursor, or VS Code

Ask your agent:

“1,200 RSUs just vested at $80. Should I sell at vest or hold for the LTCG cliff?”

With the OptionsAhoy MCP installed, your agent calls rsu_sell_vs_hold and returns the same after-tax answer this calculator computes.

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You compared one vest. The beta plans them all.

OptionsAhoy schedules every vest across years, jointly with ISO + NSO exercises and hedges, weighted by bullish, neutral, and bearish scenarios. Free during beta.

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