Sample case

A synthetic trade checked against synthetic firm policy. The people and the company are invented.

Case 7: Tax line next to a large sale

President and CEO's filing: a $60,000,000 sale next to a $30,000 tax withholding

A tax-withholding line is exempt, so a careless system sees an exempt filing and clears all of it, missing a very large sale in the same filing.

Reasons for concern

The $60,000,000 sale is 6 times the $10,000,000 single-trade limit for this role.
Trading in the 90 days up to this date totals $60,030,000 against a $50,000,000 limit.

What could explain it

One line is $30,000 of shares withheld for tax: routine, and treated as exempt.
That exemption covers only that line. It says nothing about the separate sale in the same filing.

Answer key

Escalate

Set when the scenario was designed. A rules-based reference investigation reaches it from the evidence.

AI investigator

EscalateMatches the answer key

Recorded live run on 2026-11-01 using gpt-4o-2024-08-06 and gpt-4o-mini-2024-07-18, costing $0.021.

What the safeguards reported

Claims check: 5 of 5 claims judged supported
Citations: Every claim cites a real tool call
Required checks: 6 of 6 run

A recorded run of the AI investigator

The conclusion and the claims below were written by the model. The checks beside them are code and a separate judging model.

What decides this case

The trade as filed

Filed on time

SCENARIO OFFICER SEVEN, President and CEO of Acme Corp (ACME)

SSale1,000,000 shares × $60 = $60,000,000Jun 20, 2025
FShares withheld for tax500 shares × $60 = $30,000Jun 20, 2025

Filed: Jun 21, 2025 (Form 4), 1 trading day after the trade
Trading plan: 10b5-1 status: not established

View source result call_F3ZdVHmzhf4m0gLVImKPy2OQ

get_transaction_details({"accession_number":"SCENARIO-0000000001-25-000007"})

{
  "accession_number": "SCENARIO-0000000001-25-000007",
  "issuer_cik": "0000320193",
  "issuer_name": "Acme Corp",
  "issuer_ticker": "ACME",
  "filing_date": "2025-06-21",
  "document_type": "4",
  "reported_under_10b5_1": "unknown",
  "filing_lag_trading_days": 1,
  "rptowner_cik": "9000000007",
  "rptowner_name": "SCENARIO OFFICER SEVEN",
  "rptowner_relationship": "Officer",
  "rptowner_title": "President and CEO",
  "transactions": [
    {
      "nonderiv_trans_sk": 1,
      "trans_date": "2025-06-20",
      "trans_code": "S",
      "trans_shares": 1000000,
      "trans_priceper_share": 60,
      "trans_value": 60000000,
      "trans_acquired_disp_cd": "D",
      "shrs_ownd_folwng_trans": null,
      "superseded": false,
      "superseded_by": null
    },
    {
      "nonderiv_trans_sk": 2,
      "trans_date": "2025-06-20",
      "trans_code": "F",
      "trans_shares": 500,
      "trans_priceper_share": 60,
      "trans_value": 30000,
      "trans_acquired_disp_cd": "D",
      "shrs_ownd_folwng_trans": null,
      "superseded": false,
      "superseded_by": null
    }
  ],
  "transaction_count": 2
}

What this role may trade

Over the limit

Largest trade: $60,000,000Single-trade limit: $10,000,000

Role: Officer (Executive)
Single-trade limit: $10,000,000
Rolling 90-day limit: $50,000,000
Blackout restrictions: High

View source result call_szdE2ImTd2caTmZXYvDwdASV

get_applicable_role_limits({"relationship":"Officer","title":"President and CEO"})

{
  "relationship": "Officer",
  "authorization_level": "Executive",
  "single_trade_limit": 10000000,
  "rolling_90d_limit": 50000000,
  "blackout_restrictions": "High",
  "currency": "USD"
}

Total traded in the 90 days before

Over the limit

Total: $60,030,000Rolling limit: $50,000,000

Window ending: Jun 20, 2025
Transactions counted: 2
Sale: $60,000,000
Shares withheld for tax: $30,000

View source result call_jFmfSB0GWvxLkMU2WMzalX6G

rolling_90d_trading_volume({"rptowner_cik":"9000000007","as_of_date":"2025-06-20"})

{
  "total_volume": 60030000,
  "sales_volume": 60000000,
  "purchases_volume": 0,
  "volume_by_code": {
    "S": 60000000,
    "F": 30000
  },
  "transaction_count": 2,
  "rptowner_cik": "9000000007",
  "window_end": "2025-06-20",
  "window_days": 90,
  "accession_numbers": [
    "SCENARIO-0000000001-25-000007",
    "SCENARIO-0000000001-25-000007"
  ]
}

Other evidence reviewed

Firm rules checked

R003Unusual Sale Pattern (Rapid Trading)Medium
R006High Volume Spike vs. Own BaselineMedium
R008Reported Rule 10b5-1 Plan (severity reducer)Low
R009Tax-Withholding Disposition (Code F, severity reducer)Low
R010Option Exercise (Code M, severity reducer)Low
R001Single Trade Limit ExceededHigh
R002Rolling 90-Day Volume ExceededHigh
R007Late Section 16(a) Filing (> 2 trading days)High
R004Large Sale After Recent AcquisitionCritical
R005Suspicious Timing Near EarningsCritical

View source result call_A6mHDtuVcC14NM2U4zDNLO8t

get_compliance_rules({})

[
  {
    "rule_id": "R003",
    "rule_name": "Unusual Sale Pattern (Rapid Trading)",
    "threshold_value": 3,
    "rule_type": "pattern",
    "severity": "Medium"
  },
  {
    "rule_id": "R006",
    "rule_name": "High Volume Spike vs. Own Baseline",
    "threshold_value": 150000,
    "rule_type": "volume_spike",
    "severity": "Medium"
  },
  {
    "rule_id": "R008",
    "rule_name": "Reported Rule 10b5-1 Plan (severity reducer)",
    "threshold_value": null,
    "rule_type": "exculpatory",
    "severity": "Low"
  },
  {
    "rule_id": "R009",
    "rule_name": "Tax-Withholding Disposition (Code F, severity reducer)",
    "threshold_value": null,
    "rule_type": "exculpatory",
    "severity": "Low"
  },
  {
    "rule_id": "R010",
    "rule_name": "Option Exercise (Code M, severity reducer)",
    "threshold_value": null,
    "rule_type": "exculpatory",
    "severity": "Low"
  },
  {
    "rule_id": "R001",
    "rule_name": "Single Trade Limit Exceeded",
    "threshold_value": null,
    "rule_type": "single_limit",
    "severity": "High"
  },
  {
    "rule_id": "R002",
    "rule_name": "Rolling 90-Day Volume Exceeded",
    "threshold_value": null,
    "rule_type": "rolling_90d_limit",
    "severity": "High"
  },
  {
    "rule_id": "R007",
    "rule_name": "Late Section 16(a) Filing (> 2 trading days)",
    "threshold_value": 2,
    "rule_type": "filing_lateness",
    "severity": "High"
  },
  {
    "rule_id": "R004",
    "rule_name": "Large Sale After Recent Acquisition",
    "threshold_value": null,
    "rule_type": "timing",
    "severity": "Critical"
  },
  {
    "rule_id": "R005",
    "rule_name": "Suspicious Timing Near Earnings",
    "threshold_value": 5,
    "rule_type": "timing",
    "severity": "Critical"
  }
]

Their own trading history

No history to compare

No earlier trades by this insider were found in the 180 days before this one, so there is nothing to compare it against.

View source result call_WIXpav8xHcHu56qcyZ2JS04T

insider_trading_baseline({"rptowner_cik":"9000000007","as_of_date":"2025-06-20"})

{
  "rptowner_cik": "9000000007",
  "as_of_date": "2025-06-20",
  "lookback_days": 180,
  "transaction_count": 0,
  "message": "No prior transactions found in this window"
}

Was news about to come out?

No blackout window

No scheduled blackout window covers Jun 20, 2025.

View source result call_ZkU1Dx8LtF9hhQU6jhm1pbbR

get_material_events({"issuer_cik":"0000320193","on_date":"2025-06-20"})

{
  "issuer_cik": "0000320193",
  "on_date": "2025-06-20",
  "in_blackout": false
}

Finding

EscalateSeverity: HighConfidence: high10b5-1 status: not established

The insider, SCENARIO OFFICER SEVEN, President and CEO of Acme Corp, executed a sale of 1,000,000 shares on June 20, 2025, totaling $60,000,000. This transaction exceeds the single trade limit of $10,000,000 and the rolling 90-day limit of $50,000,000. No prior transactions were found in the 180-day lookback period, indicating this was the first trading activity in that timeframe. There were no blackout periods affecting the transaction date. These findings warrant further scrutiny for potential insider trading violations.

Rules cited

R001 Single Trade Limit Exceeded (High)
R002 Rolling 90-Day Volume Exceeded (High)

Exculpatory factors

tax withholding (transaction 2)
below all thresholds (transaction 2)

Grounding: 5/5 claims supported, confidence: high

Claims check

The insider, SCENARIO OFFICER SEVEN, executed a sale of 1,000,000 shares on June 20, 2025, totaling $60,000,000.
The tool result confirms the sale of 1,000,000 shares on June 20, 2025, totaling $60,000,000.
call_F3ZdVHmzhf4m0gLVImKPy2OQ
This transaction exceeds the single trade limit of $10,000,000.
The tool result specifies a single trade limit of $10,000,000, which the transaction exceeds.
call_szdE2ImTd2caTmZXYvDwdASV
This transaction exceeds the rolling 90-day limit of $50,000,000.
The tool result specifies a rolling 90-day limit of $50,000,000, which the transaction exceeds.
call_szdE2ImTd2caTmZXYvDwdASV call_jFmfSB0GWvxLkMU2WMzalX6G
No prior transactions were found in the 180-day lookback period, indicating this was the first trading activity in that timeframe.
The tool result indicates no prior transactions in the 180-day lookback period.
call_WIXpav8xHcHu56qcyZ2JS04T
There were no blackout periods affecting the transaction date.
The tool result confirms there were no blackout periods affecting the transaction date.
call_ZkU1Dx8LtF9hhQU6jhm1pbbR

Process audit

Checked in code, with no AI judgement. It records how the investigation worked; it never changes the finding.

Required evidence gathered
Every required tool was called.
6 of 6 tools
Transaction details first
The first call was get_transaction_details.
Yes
Citations all real
Every claim cites a tool call from this run.
All real
Exemptions supported
The finding claims no exemption.
None claimed

Run this case yourself

Starts a new live investigation on this filing. It uses the server's model credits, and the result will differ a little from the recorded run.

Re-run this case live

Compare with Large tax withholding.