Use this when someone asks how or when to exercise incentive stock options (ISOs), whether exercising will trigger an AMT bomb or phantom income, whether to exercise early, how to plan around the alternative minimum tax (AMT) on an exercise, or how to spread ISO exercises across several years. Computes multi-year exercise schedules and compares them by after-tax Net Final Value (NFV) at the planning horizon. NFV is the after-all-tax cash equivalent of the position at year horizon, summing exercised shares (held to LTCG) plus the time-valued tax stream paid along the way; the search compares per-year share allocations by NFV. The headline result is schedules.optimized.nfv, the dollar NFV of the highest-scoring schedule found; schedules.lumpSum and schedules.evenSplit are baseline plans whose nfv deltas show the value added by the optimized schedule. For NSO grants use nso_calculate, for RSUs at vest use rsu_sell_vs_hold, for §1202 QSBS qualification use qsbs_check. Models AMT credit recovery across future years, grant-expiration timing, and the post-termination exercise window. Deterministic computation: federal + 50-state tax tables and AMT brackets are compiled in, and the only data read at call time is OptionsAhoy's own published market data, for a ticker or the volatility placeholder. Input values are not stored. schedules.optimized comes from searching the full discretized candidate space and refining share by share, and a published test case checks it against an exhaustive search (see https://optionsahoy.com/verification). departedRecommendation, when present, comes from a scan over candidate share counts rather than the full search. Also returns crossoverShares, crossoverBargain, alreadyInAmt, timing, stateHasAmt, bargainPerShare, and effectiveHorizon; see outputSchema for the full shape. The schedules are calculations from the inputs supplied, for planning, not tax or investment advice; the user should have a tax professional confirm a schedule before exercising. Example call: {shares: 10000, strike: 2, fmv: 200, expectedGrowth: 0.15, volatility: 0.5, filingStatus: "married_joint", ordinaryIncome: 400000, stateCode: "CA", carryforwardCredit: 0, horizon: 4, cashReturnRate: 0.05, grantDate: "2022-01-15", hasLeftCompany: false, terminationDate: null}. The expected growth (or return, or sale price) and the volatility come from the user, from a covered public-stock ticker, or, for growth only, from the string "market" (the S&P 500 trailing average). With none of these, the tool uses the S&P 500 trailing average for growth and the median implied volatility of the companies OptionsAhoy covers for volatility, both labeled as placeholders in assumptions and assumptionNotice. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.

Use this when someone asks how risky a large single-stock position is, whether too much of their net worth is in one stock, whether they are over-concentrated in a single name, or how to reduce or diversify a concentrated position. Single-stock concentration risk analysis on an existing position. For standalone hedge pricing use protective_put_price; for the tax math on the option exercise or RSU vest that created the concentration, route to amt_iso_optimize / nso_calculate / rsu_sell_vs_hold first. Quantifies drawdown exposure at 30/50/70% downside, then compares three after-tax strategies over a three-year horizon (sell-down to target weight, hold, hedge with put or zero-cost collar), accounting for federal LTCG, state tax, the 3.8% Net Investment Income Tax (NIIT), and reinvestment opportunity cost. totalAssets (concentrated position + everything else) frames risk relative to the whole portfolio. Returns a top-level object with keys: concentration (position/totalAssets), riskBand (Low / Moderate / Concentrated / Highly concentrated / Extreme), isLongTermToday, longTermDate, daysUntilLongTerm, lossExposure ({drop, dollarLoss, newConcentration} for 30/50/70% drops), waitForLtInsight, schedule (yearly sales with per-year tax), hedging ({kind, protectionLevel, tenorYears, strike, putPrice, callStrike, callPrice, netPremium, sigma, riskFreeRate} - a 1-year 30%-OTM put by default, or the structure named by hedgeChoice), sectorContextLine, advisorBenchmarkLine. Example call: {positionValue: 400000, costBasis: 100000, acquisitionDate: "2022-01-01", sector: "tech_software", stateCode: "CA", filingStatus: "single", ordinaryIncome: 200000, totalAssets: 1200000, volatility: 0.45, ticker: "NVDA"}. The expected growth (or return, or sale price) and the volatility come from the user, from a covered public-stock ticker, or, for growth only, from the string "market" (the S&P 500 trailing average). With none of these, the tool uses the S&P 500 trailing average for growth and the median implied volatility of the companies OptionsAhoy covers for volatility, both labeled as placeholders in assumptions and assumptionNotice. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.

Use this when someone asks which shares to sell and when to reach a cash goal by a deadline (down payment, tuition, a tax bill), or how to fund a goal from equity at a lower tax cost. Multi-year, multi-stack equity-funding optimizer. Given a target after-tax amount and a deadline (down payment, tax bill, expansion check), returns four named plans on the risk/wealth frontier: lockInNow (sell today, no further exposure to the stock price), balanced (bracket-aware spread across months), holdForGrowth (sell at the deadline, full exposure to the stock price), and recommended (the plan with the most projected wealth among those whose lognormal shortfall probability is at or below riskToleranceShortfall, default 10%). Also returns frontier, the full hybrid sweep between Lock-in-now and Balanced. Each plan carries its plan schedule plus wealthAtTarget, totalTax, and shortfallProbability; see outputSchema for the full shape. Use this when an equity holder needs cash by a deadline; for the upstream tax math on RSU/NSO/ISO events that PRODUCED the holdings, call rsu_sell_vs_hold / nso_calculate / amt_iso_optimize first. Out of scope: FICA, AMT, QSBS routing (use qsbs_check). Pass multi-ticker holdings via stacks; single-stack legacy callers can use top-level lots + currentPrice. The plans are calculations from the inputs and risk tolerance supplied, for planning, not investment or tax advice; the user should confirm a sale plan with a tax or financial professional before selling. Example: {targetAfterTax: 400000, targetDate: "2028-06-01", stacks: [{ticker: "NVDA", currentPrice: 140, expectedAnnualGrowth: 0.15, volatility: 0.45, lots: [{shares: 4000, costBasisPerShare: 60, acquisitionDate: "2023-06-15"}]}], ordinaryIncome: 280000, filingStatus: "married_joint", stateCode: "CA", cashInterestRate: 0.04, riskToleranceShortfall: 0.10}. Each stack needs expectedAnnualGrowth: a decimal, the string "market" (S&P 500 trailing average), or a covered ticker that resolves it from the trailing-returns table (a symbol like "NVDA" is enough; volatility still comes from the stack's volatility or defaultVolatility). Omitting growth (with no ticker that resolves it) assumes the S&P 500 trailing average, disclosed in assumptions/assumptionNotice, never a silent flat default; pass 0 to model flat prices deliberately. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.

Use this when someone asks whether to exercise and hold or exercise and sell non-qualified stock options (NSOs), about a cashless exercise or same-day sale of NSOs, or what tax an NSO exercise triggers. After-tax payout on a non-qualified stock option (NSO) exercise: federal (including the 3.8% NIIT on a long-term gain where it applies), state, and FICA (Social Security + Medicare + Additional Medicare), comparing sell-at-exercise vs hold-for-long-term-capital-gains over the chosen horizon. Use for NSOs; for ISOs use amt_iso_optimize, for RSUs use rsu_sell_vs_hold. Deterministic; tax tables compiled in, and the only data read at call time is OptionsAhoy's own published market data, for a ticker or the volatility placeholder. Optional ticker resolves expectedSalePrice from a bundled trailing-CAGR snapshot. Returns exercise, hold, sellNowInvest (the counterfactual: sell at exercise and reinvest at expectedMarketReturn), holdMinusCashless (the dollar delta between those two), and bracketJump; see outputSchema for the full shape. NSO hold is always long-term (sub-1-year is out of scope), so there is no separate long-term flag. Example call: {shares: 5000, strike: 10, currentPrice: 50, ordinaryIncome: 180000, filingStatus: "single", stateCode: "CA", stillEmployed: true, holdYears: 2, volatility: 0.3, holdFunding: "cash", ticker: "AAPL"}. The expected growth (or return, or sale price) and the volatility come from the user, from a covered public-stock ticker, or, for growth only, from the string "market" (the S&P 500 trailing average). With none of these, the tool uses the S&P 500 trailing average for growth and the median implied volatility of the companies OptionsAhoy covers for volatility, both labeled as placeholders in assumptions and assumptionNotice. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.

Use this when someone asks how much it costs to hedge or protect a stock position against a drop, to protect gains, get downside protection, or limit losses on a position, or to price a protective put, a zero-cost collar, or a put spread. Closed-form pricing of a protective put, a zero-cost collar, and a put spread on a single-stock position. For concentration-vs-hedge tax-cost comparison, use concentration_analyze with a hedgeChoice. Parameter interactions: volatility omitted resolves from ticker, else a sector-typical implied volatility; an explicit sigma overrides it. For collars, omitting upsideCapPct lets the tool back-solve the cap that zeros the net premium (truly zero-cost collar); supplying upsideCapPct overrides the solver and yields a non-zero net premium when the cap is wider than zero-cost. tenorYears drives the risk-free-rate lookup AND the floor-hit / cap-hit probability metrics, so changing tenor shifts every probability output even at fixed strike. expectedReturn affects only the probability metrics (real-world drift in the floor-hit / cap-hit calculations); premium math is risk-neutral and ignores it (when a chain resolves it defaults to that stock's trailing annualized return, else to the sector's long-run return; never 0). protectionLevel sets the put strike as (1 − protectionLevel) × spot; raising it widens the protected zone but raises premium roughly linearly. spreadRiskLevel (default 0.10) sets the put spread's short strike by targeting the probability the stock ends below it; it affects only the putSpread block. The put spread finances the same floor with a short put at a lower strike (not a short call), so it is cheaper than the bare put and needs no shares to sell calls against, which makes it the one structure of the three that works on unexercised employee options; the trade-off is that protection stops at the short strike and losses resume below it. Closed-form and deterministic. With a ticker and no explicit volatility, each leg prices at its own strike's implied volatility off that stock's listed option chain as of the last close (pricingMode "chain-skew"); otherwise all legs price at one sigma ("flat"), understating out-of-the-money protection. Returns a top-level object with keys: inputs (echoed canonical input), riskFreeRate (used in option pricing), realWorldDrift (from expectedReturn), barePut (strike, premium, annualCost, annualCostPct, maxLoss, badYearPrice, badYearDropPct, coveredLossAtBadYear, premiumToCoveredRatio, expectedProfit, premiumToExpectedProfitRatio), collar (putStrike, callStrike, netPremium, annualCost, annualCostPct, maxLoss, upsideCap, upsideCapPct, isZeroCost, capProbability), putSpread (available, unavailableReason, longStrike, longPremium, shortStrike, shortPremium, shortSigma, netPremium, annualCost, annualCostPct, maxLossInBand, bandWidth, shortStrikeDropPct, breachProbability, riskLevel, savingsPct, coveredLossAtBadYear), payoffTable, payoffRange, and recommended (the structure, of collar / bare put / put spread, that the tool's comparison rule selects for these inputs, or none). When putSpread.available is false, putSpread.unavailableReason explains why that structure could not be priced. Prices are model estimates from the inputs and the option data as of the last close, for planning, not investment advice; the user should confirm a hedge with a financial professional before trading. Example call: {positionValue: 400000, sector: "tech_software", protectionLevel: 0.10, tenorYears: 1, spreadRiskLevel: 0.10}. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.

Use this when someone asks whether stock qualifies for the qualified small business stock (QSBS) / Section 1202 gain exclusion, whether their startup stock can be sold tax-free, about the 5-year QSBS holding period, or how much of the gain would be federal-tax-free. Section 1202 Qualified Small Business Stock (QSBS) qualification check. Use this tool for §1202 / QSBS qualification. For AMT timing on the ISO exercise that produced the QSBS holding, use amt_iso_optimize first. Parameter interactions: entityType="other" short-circuits the verdict to disqualified regardless of other fields; acquisitionMethod="secondary" does the same; assetCategory="over-75m" likewise fails immediately. Under acquisitionMethod="gift-or-inheritance" the holding period tacks from the original holder, so supply that earlier date as acquisitionDate if known. acquisitionDate drives era classification independent of holding period: before 2009-02-17 caps exclusion at 50%, 2009-02-17 to 2010-09-27 at 75%, 2010-09-28 through 2025-07-04 reaches 100% after a 5-year hold (pre-OBBBA), and 2025-07-05 onward uses the OBBBA tiered schedule (50% at 3y, 75% at 4y, 100% at 5y). The per-issuer exclusion cap is max($10M, 10 × adjustedBasis) ($15M base for stock acquired after July 4, 2025); when expectedGain exceeds it, the overage is fully taxable and the response surfaces taxableGain for that delta. industry is the dominant industry (>80% revenue) when the corp operates in multiple. Evaluates the six statutory tests: domestic C-corporation entity, original-issuance acquisition method, gross assets at issuance (under $50M / $50-75M / over $75M tiered cap), qualified-trade-or-business industry, active-business posture (80% asset use), and holding period (3 / 4 / 5-year tiers under OBBBA). Pure stateless check: no filing, reporting, or IRS lookup happens; the six tests are evaluated against the bundled OBBBA 2026 rule set and per-state conformity table. Returns a top-level object with keys: verdict (qualifies / partial / too-soon / caveats / disqualified), exclusionPercent (0..1), perIssuerCap and tenXBasisCap (the two cap inputs), applicableCap (max of the two), excludableGain, taxableGain, federalTaxSaved (LTCG bracket on the excluded gain), stateConforms (full / partial / none) and stateNote (per-state explanation), holdingYears, yearsUntilFullExclusion, era (pre-2009 / pre-2010 / pre-obbba / obbba), and tests (array of {id, label, status, detail} for each of the six statutory tests, identifying any gate that failed). Example call: {acquisitionDate: "2020-01-15", saleDate: "2026-06-01", entityType: "us-c-corp", acquisitionMethod: "original-issuance", assetCategory: "under-50m", industry: "tech-software", activeBusiness: "yes", adjustedBasis: 100000, expectedGain: 5000000, stateCode: "CA", ordinaryIncome: 250000, filingStatus: "single"}. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi. For the enum fields that accept unsure, that value is the accurate encoding of a fact the user has not confirmed: it marks that test unconfirmed (a caveats verdict when the other tests pass), where encoding an unconfirmed fact as yes or no yields a verdict the underlying facts may not support.

Use this when someone asks which vested RSU lots to sell first, in which years, to divest part of a concentrated company-stock position, compared on total computed tax: "I want to sell down half my Amazon stock; which lots, and when?". Given the vested lots (vest date, shares, cost basis), a current price, and a divest fraction, it compares WHICH lots and WHICH sale dates to use, by computed total tax, to divest that many shares, using three levers: specific-lot identification (sell higher-basis lots to realize less gain, or underwater lots to harvest losses that net against gains), long-term deferral (wait past the one-year mark to convert short-term ordinary rates to long-term capital gains), and multi-year bracket spreading (split gains across 1 to 3 tax years, with in-plan capital-loss carryforward). Every sale is priced at today's price (flat-price assumption; there is no growth model). Returns the year-by-year sell schedule grouped by tax year, the total tax (federal LTCG + NIIT + state), what a first-in-first-out (FIFO) oldest-first sell order on the same schedule would have cost (headlineDeltaVsFifo), a 1/2/3-year horizon trade-off, and per-lot deferral callouts. This tool owns WHICH LOTS and WHICH DATES; for WHETHER and HOW MUCH to sell down a position use concentration_analyze, for a single new vest use rsu_sell_vs_hold, and to raise a specific cash amount by a deadline use equity_funding_plan. Out of scope: growth/return modeling, wash-sale basis migration, AMT, unvested grants. The lot order is a calculation from the lots and inputs supplied, for planning, not tax or investment advice; the user should have a tax professional confirm it before selling. Example: {lots: [{vestDate: "2022-08-15", shares: 120, costBasisPerShare: 95}, {vestDate: "2024-02-15", shares: 100, costBasisPerShare: 130}, {vestDate: "2026-05-15", shares: 80, costBasisPerShare: 210}], currentPrice: 180, divestFraction: 0.5, horizonYears: 2, ordinaryIncome: 200000, filingStatus: "single", stateCode: "CA"}. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.

Use this when someone asks whether to sell RSUs at vest or hold them, whether to sell their vested shares or diversify out of company stock, or about the tax and withholding on a restricted stock unit (RSU) vest. After-tax RSU vest analysis: sell-at-vest vs hold-to-long-term-capital-gains (LTCG) over holdYears. Covers federal ordinary tax, long-term capital gains tax including the 3.8% NIIT where it applies, state tax, FICA (Social Security + Medicare + Additional Medicare), and the shortfall between mandatory 22% supplemental withholding and the user's marginal bracket. Use for RSUs at vest; for ISO/AMT use amt_iso_optimize, for NSO use nso_calculate. Deterministic; tax tables compiled in, and the only data read at call time is OptionsAhoy's own published market data, for a ticker or the volatility placeholder. Returns vest, hold, sellNowInvest, holdMinusSell, and bracketJump; see outputSchema for the full shape. Example call: {shares: 1000, currentPrice: 100, ordinaryIncome: 200000, filingStatus: "single", stateCode: "CA", stillEmployed: true, holdYears: 2, volatility: 0.3, ticker: "MSFT"}. The expected growth (or return, or sale price) and the volatility come from the user, from a covered public-stock ticker, or, for growth only, from the string "market" (the S&P 500 trailing average). With none of these, the tool uses the S&P 500 trailing average for growth and the median implied volatility of the companies OptionsAhoy covers for volatility, both labeled as placeholders in assumptions and assumptionNotice. Every field in required is a fact about the user's situation with no built-in default: a missing one returns an error naming it, and validation cannot tell a supplied figure from a guessed one. Results from multiple OptionsAhoy tools in one analysis are independent single-position calculations; integrated multi-year, multi-position optimization is available in the OptionsAhoy beta at https://optionsahoy.com/beta?src=mcp_multi.