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OptionsAhoy: Stock Equity and Tax Optimizer

qsbs_check

Read-onlyIdempotent

Check if startup stock qualifies for the QSBS Section 1202 gain exclusion and see how much of the sale gain is federally tax-free based on holding period, entity, and asset tests.

Instructions

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 listed in required is a fact about the user's situation with no built-in default: a call missing a required field returns an error naming the field rather than an estimated result, and a number from any other source is accepted as-is, because a syntactically valid figure passes validation with no provenance check. The math runs inside the tool with no randomness and no model inference. 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 yields a partial verdict flagging that test as unconfirmed, where encoding an unconfirmed fact as yes or no yields a verdict the underlying facts may not support.

Input Schema

TableJSON Schema
NameRequiredDescriptionDefault
industryYes§1202 Test 4: Industry classification of the corporation. Four values qualify: tech-software, manufacturing, biotech-research, retail-wholesale. Specified service trades or businesses (law, engineering, architecture, accounting-actuarial, consulting, finance, health-services, performing-arts) do NOT qualify, and farming, extraction and hospitality are separately excluded, so they do not qualify either. other-services and unsure return a caveated verdict rather than a pass or fail.
saleDateYesPlanned or actual sale date (YYYY-MM-DD). Together with acquisitionDate determines holdingYears.
stateCodeYesTwo-letter US state code. Drives the state-conformity verdict: CA/AL/PA/MS do not conform (full state tax owed); HI/MA partial; NJ 2026-01-01 conformity switch; most others fully conform.
entityTypeYes§1202 Test 1: Type of issuer at the time of acquisition. Only 'us-c-corp' qualifies. S-corps, LLCs, partnerships, and foreign entities fail.
expectedGainYesExpected total gain on sale, USD. Compared against the per-issuer exclusion cap to compute excludableGain and taxableGain. Must come from the user.
filingStatusYesFederal filing status. Drives the LTCG bracket on any non-excluded gain and the NIIT MAGI threshold.
adjustedBasisYesAdjusted basis of the QSBS shares, USD. Used in the 10× basis cap: the per-issuer exclusion cap is max($10M, 10 × adjustedBasis). Must come from the user.
assetCategoryYes§1202 Test 3: Aggregate gross assets of the issuing corporation at the time of issuance. 'under-50m' qualifies pre-OBBBA. '50m-to-75m' qualifies ONLY under OBBBA 2026+ (post-2025-07-05). 'over-75m' never qualifies. 'unsure' returns a partial verdict.
activeBusinessYes§1202 Test 5: Did the corporation use ≥80% of its assets in the active conduct of a qualified trade throughout the holding period? 'yes' qualifies. 'no' fails. 'unsure' returns a partial verdict (user should confirm with their CFO).
ordinaryIncomeYesAnnual ordinary income, USD. Baseline for the federal LTCG bracket on any taxable gain. Must come from the user. This is taxable income after deductions, not gross wages: the engine applies no standard or itemized deduction to it.
acquisitionDateYesDate the QSBS shares were acquired (YYYY-MM-DD). Drives the holding-period test and the era classification (50% pre-2009 era, 75% pre-2010 era, 100% after a 5-year hold for acquisitions from 2010-09-28 through 2025-07-04, OBBBA tiered after 2025-07-05).
acquisitionMethodYes§1202 Test 2: How the user obtained the shares. 'original-issuance' (direct from the company) qualifies. 'gift-or-inheritance' tacks the original holder's basis and clock. 'secondary' (bought on a secondary market) does NOT qualify. 'unsure' triggers a partial verdict.

Output Schema

TableJSON Schema
NameRequiredDescriptionDefault
eraYesAcquisition-era classification that sets the exclusion schedule (50% pre-2009 era, 75% pre-2010 era, 100% at 5y pre-OBBBA, tiered 50/75/100% at 3/4/5y under OBBBA).
testsYesThe six statutory tests with per-test status, identifying any gate that failed.
verdictYesOverall verdict. "partial" = qualifies but at a sub-100% exclusion tier (e.g. an OBBBA 3- or 4-year hold gives 50% or 75%). "caveats" = qualifies, but one or more tests returned "unsure" (pass conditional on facts the caller marked unknown). "too-soon" = the holding period has not reached any exclusion tier yet.
stateNoteNoPer-state conformity explanation. May be omitted.
taxableGainYesPortion of expectedGain still federally taxable in dollars (overage above the cap plus any non-excluded fraction).
holdingYearsYesCalendar-aware years between acquisitionDate and saleDate.
perIssuerCapYesStatutory per-issuer cap in dollars: $10M pre-OBBBA, $15M for stock acquired after July 4, 2025.
tenXBasisCapYes10 x adjustedBasis cap in dollars.
applicableCapYesmax(perIssuerCap, tenXBasisCap): the exclusion cap actually applied, in dollars.
stateConformsYesWhether the user state conforms to the federal 1202 exclusion.
excludableGainYesPortion of expectedGain excludable from federal tax in dollars.
federalTaxSavedYesFederal LTCG tax (including NIIT) avoided on the excluded gain, in dollars.
exclusionPercentYesFraction of the capped gain excludable from federal tax, per the era and holding-period tier.
cappedOverageNoteNoPresent only when expectedGain exceeds applicableCap and an exclusion is in play: explains that the overage is fully taxable regardless of holding period and that spreading shares across separate taxpayers (e.g. non-grantor trusts) can multiply the per-issuer exclusion. Omitted otherwise.
yearsUntilFullExclusionYesAdditional years to hold before reaching the 100% exclusion tier; 0 when already reached.

Schema Changelog

Changes observed during successful MCP inspections.

  1. Addedv1.10.1
  2. Removedv1.9.8
  3. Changed7 schema fields changedv1.9.7
    • changedInput schema / properties / acquisitionDate / description
      Previous value: -"Date the QSBS shares were acquired (YYYY-MM-DD). Drives the holding-period test and the era classification (50% pre-2009, 75% 2009-2010, 100% 2010-2025-07-04, OBBBA tiered after 2025-07-05)."New value: +"Date the QSBS shares were acquired (YYYY-MM-DD). Drives the holding-period test and the era classification (50% pre-2009 era, 75% pre-2010 era, 100% after a 5-year hold for acquisitions from 2010-09-28 through 2025-07-04, OBBBA tiered after 2025-07-05)."
    • addedInput schema / properties / stateCode / enum
      Added value: +[
      +  "AK",
      +  "AL",
      +  "AR",
      +  "AZ",
      +  "CA",
      +  "CO",
      +  "CT",
      +  "DC",
      +  "DE",
      +  "FL",
      +  "GA",
      +  "HI",
      +  "IA",
      +  "ID",
      +  "IL",
      +  "IN",
      +  "KS",
      +  "KY",
      +  "LA",
      +  "MA",
      +  "MD",
      +  "ME",
      +  "MI",
      +  "MN",
      +  "MO",
      +  "MS",
      +  "MT",
      +  "NC",
      +  "ND",
      +  "NE",
      +  "NH",
      +  "NJ",
      +  "NM",
      +  "NV",
      +  "NY",
      +  "OH",
      +  "OK",
      +  "OR",
      +  "PA",
      +  "RI",
      +  "SC",
      +  "SD",
      +  "TN",
      +  "TX",
      +  "UT",
      +  "VA",
      +  "VT",
      +  "WA",
      +  "WI",
      +  "WV",
      +  "WY"
      +]
    • removedInput schema / properties / stateCode / pattern
      Removed value: -"^[A-Z]{2}$"
    • changedOutput schema / properties / era / description
      Previous value: -"Acquisition-era classification that sets the exclusion schedule (50% pre-2009, 75% 2009-2010, 100% at 5y pre-OBBBA, tiered 50/75/100% at 3/4/5y under OBBBA)."New value: +"Acquisition-era classification that sets the exclusion schedule (50% pre-2009 era, 75% pre-2010 era, 100% at 5y pre-OBBBA, tiered 50/75/100% at 3/4/5y under OBBBA)."
    • changedOutput schema / properties / perIssuerCap / description
      Previous value: -"The $10M statutory per-issuer cap in dollars."New value: +"Statutory per-issuer cap in dollars: $10M pre-OBBBA, $15M for stock acquired after July 4, 2025."
    • changedOutput schema / properties / tests / description
      Previous value: -"The eight statutory tests with per-test status, so an agent can show exactly which gate failed."New value: +"The six statutory tests with per-test status, so an agent can show exactly which gate failed."
    • changedOutput schema / properties / verdict / description
      Previous value: -"Overall verdict. \"partial\"/\"caveats\" mean some tests came back unsure; \"too-soon\" means the holding period has not reached an exclusion tier yet."New value: +"Overall verdict. \"partial\" = qualifies but at a sub-100% exclusion tier (e.g. an OBBBA 3- or 4-year hold gives 50% or 75%). \"caveats\" = qualifies, but one or more tests returned \"unsure\" (pass conditional on facts the caller marked unknown). \"too-soon\" = the holding period has not reached any exclusion tier yet."
  4. Changed1 schema field changedv1.9.5
    • addedOutput schema / properties / cappedOverageNote
      Added value: +{
      +  "description": "Present only when expectedGain exceeds applicableCap and an exclusion is in play: explains that the overage is fully taxable regardless of holding period and that spreading shares across separate taxpayers (e.g. non-grantor trusts) can multiply the per-issuer exclusion. Omitted otherwise.",
      +  "type": "string"
      +}
  5. Changed1 schema field changedv1.9.2
    • changedOutput schema / (root)
      Previous value: -nullNew value: +{
      +  "description": "Section 1202 QSBS qualification result. All dollar amounts are USD.",
      +  "properties": {
      +    "applicableCap": {
      +      "description": "max(perIssuerCap, tenXBasisCap): the exclusion cap actually applied, in dollars.",
      +      "type": "number"
      +    },
      +    "era": {
      +      "description": "Acquisition-era classification that sets the exclusion schedule (50% pre-2009, 75% 2009-2010, 100% at 5y pre-OBBBA, tiered 50/75/100% at 3/4/5y under OBBBA).",
      +      "enum": [
      +        "pre-2009",
      +        "pre-2010",
      +        "pre-obbba",
      +        "obbba"
      +      ],
      +      "type": "string"
      +    },
      +    "excludableGain": {
      +      "description": "Portion of expectedGain excludable from federal tax in dollars.",
      +      "type": "number"
      +    },
      +    "exclusionPercent": {
      +      "description": "Fraction of the capped gain excludable from federal tax, per the era and holding-period tier.",
      +      "enum": [
      +        0,
      +        0.5,
      +        0.75,
      +        1
      +      ],
      +      "type": "number"
      +    },
      +    "federalTaxSaved": {
      +      "description": "Federal LTCG tax (including NIIT) avoided on the excluded gain, in dollars.",
      +      "type": "number"
      +    },
      +    "holdingYears": {
      +      "description": "Calendar-aware years between acquisitionDate and saleDate.",
      +      "type": "number"
      +    },
      +    "perIssuerCap": {
      +      "description": "The $10M statutory per-issuer cap in dollars.",
      +      "type": "number"
      +    },
      +    "stateConforms": {
      +      "description": "Whether the user state conforms to the federal 1202 exclusion.",
      +      "enum": [
      +        "full",
      +        "partial",
      +        "none"
      +      ],
      +      "type": "string"
      +    },
      +    "stateNote": {
      +      "description": "Per-state conformity explanation. May be omitted.",
      +      "type": "string"
      +    },
      +    "taxableGain": {
      +      "description": "Portion of expectedGain still federally taxable in dollars (overage above the cap plus any non-excluded fraction).",
      +      "type": "number"
      +    },
      +    "tenXBasisCap": {
      +      "description": "10 x adjustedBasis cap in dollars.",
      +      "type": "number"
      +    },
      +    "tests": {
      +      "description": "The eight statutory tests with per-test status, so an agent can show exactly which gate failed.",
      +      "items": {
      +        "properties": {
      +          "detail": {
      +            "description": "One-line explanation of the test outcome.",
      +            "type": "string"
      +          },
      +          "id": {
      +            "description": "Stable test identifier.",
      +            "type": "string"
      +          },
      +          "label": {
      +            "description": "Human-readable test name.",
      +            "type": "string"
      +          },
      +          "status": {
      +            "description": "\"wait\" means the test will pass with more holding time.",
      +            "enum": [
      +              "pass",
      +              "fail",
      +              "unsure",
      +              "wait"
      +            ],
      +            "type": "string"
      +          }
      +        },
      +        "required": [
      +          "id",
      +          "label",
      +          "status",
      +          "detail"
      +        ],
      +        "type": "object"
      +      },
      +      "type": "array"
      +    },
      +    "verdict": {
      +      "description": "Overall verdict. \"partial\"/\"caveats\" mean some tests came back unsure; \"too-soon\" means the holding period has not reached an exclusion tier yet.",
      +      "enum": [
      +        "qualifies",
      +        "partial",
      +        "too-soon",
      +        "caveats",
      +        "disqualified"
      +      ],
      +      "type": "string"
      +    },
      +    "yearsUntilFullExclusion": {
      +      "description": "Additional years to hold before reaching the 100% exclusion tier; 0 when already reached.",
      +      "type": "number"
      +    }
      +  },
      +  "required": [
      +    "verdict",
      +    "exclusionPercent",
      +    "perIssuerCap",
      +    "tenXBasisCap",
      +    "applicableCap",
      +    "excludableGain",
      +    "taxableGain",
      +    "federalTaxSaved",
      +    "stateConforms",
      +    "holdingYears",
      +    "yearsUntilFullExclusion",
      +    "era",
      +    "tests"
      +  ],
      +  "type": "object"
      +}
  6. Changed12 schema fields changedv1.2.2
    • addedInput schema / properties / acquisitionDate / description
      Added value: +"Date the QSBS shares were acquired (YYYY-MM-DD). Drives the holding-period test and the era classification (50% pre-2009, 75% 2009-2010, 100% 2010-2025-07-04, OBBBA tiered after 2025-07-05)."
    • addedInput schema / properties / acquisitionMethod / description
      Added value: +"§1202 Test 2: How the user obtained the shares. 'original-issuance' (direct from the company) qualifies. 'gift-or-inheritance' tacks the original holder's basis and clock. 'secondary' (bought on a secondary market) does NOT qualify. 'unsure' triggers a partial verdict."
    • addedInput schema / properties / activeBusiness / description
      Added value: +"§1202 Test 5: Did the corporation use ≥80% of its assets in the active conduct of a qualified trade throughout the holding period? 'yes' qualifies. 'no' fails. 'unsure' returns a partial verdict (user should confirm with their CFO)."
    • addedInput schema / properties / adjustedBasis / description
      Added value: +"Adjusted basis of the QSBS shares, USD. Used in the 10× basis cap: the per-issuer exclusion cap is max($10M, 10 × adjustedBasis)."
    • addedInput schema / properties / assetCategory / description
      Added value: +"§1202 Test 3: Aggregate gross assets of the issuing corporation at the time of issuance. 'under-50m' qualifies pre-OBBBA. '50m-to-75m' qualifies ONLY under OBBBA 2026+ (post-2025-07-05). 'over-75m' never qualifies. 'unsure' returns a partial verdict."
    • addedInput schema / properties / entityType / description
      Added value: +"§1202 Test 1: Type of issuer at the time of acquisition. Only 'us-c-corp' qualifies. S-corps, LLCs, partnerships, and foreign entities fail."
    • addedInput schema / properties / expectedGain / description
      Added value: +"Expected total gain on sale, USD. Compared against the per-issuer exclusion cap to compute excludableGain and taxableGain."
    • addedInput schema / properties / filingStatus / description
      Added value: +"Federal filing status. Drives the LTCG bracket on any non-excluded gain and the NIIT MAGI threshold."
    • addedInput schema / properties / industry / description
      Added value: +"§1202 Test 4: Industry classification of the corporation. Qualified-trade-or-business industries qualify (tech-software, manufacturing, biotech-research, retail-wholesale, hospitality, etc.). Specified service trades or businesses (law, engineering, architecture, accounting-actuarial, consulting, finance, farming, extraction, health-services, performing-arts) generally do NOT qualify."
    • addedInput schema / properties / ordinaryIncome / description
      Added value: +"Annual W-2 ordinary income, USD. Baseline for the federal LTCG bracket on any taxable gain."
    • addedInput schema / properties / saleDate / description
      Added value: +"Planned or actual sale date (YYYY-MM-DD). Together with acquisitionDate determines holdingYears."
    • addedInput schema / properties / stateCode / description
      Added value: +"Two-letter US state code. Drives the state-conformity verdict: CA/AL/PA/MS do not conform (full state tax owed); HI/MA partial; NJ 2026-01-01 conformity switch; most others fully conform."
  7. First observedv1.2.0

TDQS

A4.9/5.0
Behavior5/5

Does the description disclose side effects, auth requirements, rate limits, or destructive behavior?

Annotations already mark the tool readOnly and idempotent, and the description adds substantive behavioral context: it is a pure stateless check with no filing, reporting, or IRS lookup, deterministic math with no randomness or model inference, and required-field errors rather than estimated defaults. It also discloses the 'unsure' partial-verdict behavior and provenance limits.

Agents need to know what a tool does to the world before calling it. Descriptions should go beyond structured annotations to explain consequences.

Conciseness4/5

Is the description appropriately sized, front-loaded, and free of redundancy?

The description is long, but the tool is a 12-parameter statutory tax calculation and nearly every paragraph adds operational detail. It loses a point for redundancy ('Section 1202 Qualified Small Business Stock...' appears more than once) and a beta-promotion sentence that is not needed for tool selection.

Shorter descriptions cost fewer tokens and are easier for agents to parse. Every sentence should earn its place.

Completeness5/5

Given the tool's complexity, does the description cover enough for an agent to succeed on first attempt?

For a complex statutory test with 12 required inputs and an output schema, the description is fully sufficient: it explains all six tests, return keys, edge cases, state conformity, required-field behavior, and provides an example call. Nothing needed to call the tool correctly is missing.

Complex tools with many parameters or behaviors need more documentation. Simple tools need less. This dimension scales expectations accordingly.

Parameters5/5

Does the description clarify parameter syntax, constraints, interactions, or defaults beyond what the schema provides?

Although the schema covers all 12 parameters individually, the description adds cross-parameter semantics the schema cannot express: entityType/acquisitionMethod/assetCategory short-circuit values, gift-or-inheritance holding-period tacking, era classification dates, the per-issuer cap interaction with expectedGain, and the industry >80% revenue rule. This materially improves correct invocation.

Input schemas describe structure but not intent. Descriptions should explain non-obvious parameter relationships and valid value ranges.

Purpose5/5

Does the description clearly state what the tool does and how it differs from similar tools?

The description opens with concrete user intents: whether stock qualifies for QSBS / Section 1202 gain exclusion, whether startup stock can be sold tax-free, the 5-year holding period, and how much gain would be federal-tax-free. It names the exact resource and differentiates from the closest sibling by directing AMT-timing questions to amt_iso_optimize.

Agents choose between tools based on descriptions. A clear purpose with a specific verb and resource helps agents select the right tool.

Usage Guidelines5/5

Does the description explain when to use this tool, when not to, or what alternatives exist?

It gives explicit when-to-use triggers and states a key exclusion: 'For AMT timing on the ISO exercise that produced the QSBS holding, use amt_iso_optimize first.' This is sufficient to route an agent to the correct tool among the siblings.

Agents often have multiple tools that could apply. Explicit usage guidance like "use X instead of Y when Z" prevents misuse.