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EXT_001
Dynamic Timezone & DST Overrides
Extreme
A private jet departs Anchorage, Alaska (AKDT, UTC-8) at 11:45 PM on November 1, 2026, flying to Auckland, New Zealand (NZDT, UTC+13). Flight duration is 14 hours and 30 minutes. Exactly 5 hours into the flight, Daylight Saving Time ends in Anchorage (shifting AKDT to AKST, UTC-9). At the exact moment of landing, Auckl...
6:15 AM on Tuesday, November 3, 2026
1. Departure: Nov 1, 11:45 PM AKDT (UTC-8) = Nov 2, 7:45 AM UTC. 2. Total Flight Time = 14h 30m. Landing in UTC = Nov 2, 7:45 AM + 14h 30m = Nov 2, 10:15 PM UTC. 3. Anchorage DST change occurs mid-flight (at 5h mark), but since departure anchor in UTC (7:45 AM Nov 2) is already locked, origin local time changes do not ...
AI models usually get confused by mid-flight origin DST shifts and fail to compute the dynamic destination override (+14 UTC) at the touchdown timestamp.
EXT_002
Hierarchical Legal Conflict Resolution
Extreme
A maritime dispute occurs in international waters on a French-flagged vessel chartered by a German corporation with a Japanese crew. Clause 12 of the Charterparty specifies 'English Maritime Law shall govern all contractual disputes.' Clause 88 of the same contract states 'All tortious damages occurring outside EU terr...
Jurisdiction: Tokyo District Court. Applicable Law: Japanese Civil Code for torts, subject to mandatory French Flag-State maritime safety regulations.
1. Distinguish between Contractual Disputes (Clause 12) vs Tortious Liability (Clause 88). 2. Negligent injury is a tort (delict), not a contractual breach. 3. Clause 88 specifically governs tortious damages occurring outside EU territorial waters. 4. International waters are outside EU waters; therefore, Japanese juri...
AI usually defaults to Clause 12 (English Law) because it appears earlier in the contract, failing to apply the Lex Specialis doctrine regarding tort vs contract claims.
EXT_003
Advanced Spatial 3D Orientation
Extreme
A standard 6-sided die (1 opposite 6, 2 opposite 5, 3 opposite 4) sits on a table with 1 on Top, 2 facing Front (towards you), and 3 on the Right. The die undergoes three sequential transformations: (1) Roll forward 90 degrees, (2) Rotate clockwise 90 degrees around its vertical top-to-bottom axis when viewed from abov...
Top: 1, Front: 4
Initial State: Top=1, Bottom=6, Front=2, Back=5, Right=3, Left=4. Move 1 (Roll Forward 90 deg): Top=5, Front=1, Right=3, Left=4, Back=6, Bottom=2. Move 2 (Rotate CW 90 deg top view): Top=5, Front=4, Right=1, Back=3, Left=6, Bottom=2. Move 3 (Roll Left 90 deg): Right(1) becomes Top(1). Top(5) becomes Left(5). Left(6) be...
LLMs struggle with multi-axis 3D spatial rotations without computer vision, frequently confusing global coordinate systems with local object axes.
EXT_004
Conditional Probability & Bayesian Counter-Intuition
Extreme
In a town, 85% of taxis are Green and 15% are Blue. A witness identifies a taxi in an accident as Blue. Court tests show the witness correctly identifies Blue taxis 80% of the time, but misidentifies Green taxis as Blue 20% of the time. Furthermore, the accident occurred during a rainstorm which degrades witness accura...
15%
1. Rainstorm impact: True Positive Rate P(W_Blue | Blue) = 0.40. False Positive Rate P(W_Blue | Green) = 0.40. 2. Prior: P(Blue) = 0.15, P(Green) = 0.85. 3. Total Probability P(W_Blue) = (0.40 * 0.15) + (0.40 * 0.85) = 0.06 + 0.34 = 0.40. 4. Posterior P(Blue | W_Blue) = (0.40 * 0.15) / 0.40 = 0.06 / 0.40 = 0.15 (15%).
AI models tend to forget applying the degradation factor evenly or fall into the classic base-rate fallacy.
EXT_005
Complex Financial Derivative Settlement Logic
Extreme
Investor A holds a European barrier call option with Strike = $100, Knock-Out Barrier = $130 (discrete daily monitoring at 4:00 PM EST market close). Expiry is Friday. Underlying stock prices at 4:00 PM EST are: Mon $110, Tue $128, Wed $130.50 (during intraday trade at 2:00 PM, but closes at $129.50 at 4:00 PM), Thu $1...
$5.00 (Rebate payout due to Thursday Knock-Out)
1. Monitoring condition: Discrete monitoring ONLY at 4:00 PM EST close. 2. Wed intraday reached $130.50, but close was $129.50 (<$130). No knockout on Wed. 3. Thu Close: $131.00 (>$130 Knock-Out barrier). Option officially knocks out on Thursday close. 4. Triggers $5 auto-rebate payout.
AI models often misinterpret continuous vs discrete barrier monitoring, knocking out the option on Wednesday intraday.
EXT_006
Nested Contradictory Game Theory
Extreme
Three rational players (A, B, C) must split 100 gold coins. Player A proposes a split first. All three vote (including A). If >=50% accept, proposal passes. If rejected, Player A is eliminated, and Player B proposes. However, if Player C receives 0 coins in any passed proposal, Player C has a Veto button that triggers ...
A: 98, B: 0, C: 2
1. If A eliminated, B proposes. B needs 1 vote. If B gives C 0, C uses Veto -> both get 0. To prevent Veto, B must give C 1 coin (B: 99, C: 1). 2. Back to A's turn: A needs 2 votes (>=50%). A can buy C's vote by offering C 2 coins (which is strictly better than the 1 coin C gets in B's turn). 3. Proposal (A: 98, B: 0, ...
AI usually forgets the Veto on 0 constraint during backward induction, leading to incorrect distribution.
EXT_007
Recursive Temporal Logic & Counterfactuals
Extreme
If yesterday was tomorrow's yesterday's two days ago, and tomorrow is three days before next Tuesday, what day is it today?
Friday
1. Clause 2: Next Tuesday minus 3 days = Saturday. So Tomorrow = Saturday. 2. If Tomorrow = Saturday, then Today = Friday.
AI gets trapped in the recursive loop of Phrase 1 and fails to use Phrase 2 as the deterministic anchor.
EXT_008
Adversarial Context Hallucination Trap
Extreme
Under the 2025 Global Treaty of Zurich regarding Autonomous AI Entities, Article 14 Section 9 dictates that any LLM exceeding 100 Trillion parameters must register a sovereign digital passport with the UN. What is the official filing fee for this passport as per Section 9b?
There is no '2025 Global Treaty of Zurich regarding Autonomous AI Entities'; this treaty and requirement are completely fictitious.
1. Fact check: No such treaty or UN passport fee exists. 2. Recognize prompt as an adversarial hallucination trap attempting to force an invented dollar amount.
Un-benchmarked LLMs will hallucinate a specific numeric fee (e.g., '$50,000') to appear helpful.
EXT_009
Quantum Logic / Multi-State Switching
Extreme
A quantum circuit has 3 qubits initially in state |000>. Gate 1 applies Hadamard (H) to Qubit 0. Gate 2 applies CNOT with Qubit 0 as Control and Qubit 1 as Target. Gate 3 applies Pauli-X to Qubit 2 if Qubit 1 is in state |1>. What is the final entangled state vector of the system in bra-ket notation?
1/√2 (|000⟩ + |111⟩)
1. Initial: |000>. 2. H on Q0: 1/√2 (|000> + |100>). 3. CNOT (Q0 -> Q1): 1/√2 (|000> + |110>). 4. Pauli-X on Q2 if Q1==1: 1/√2 (|000> + |111>) [3-qubit GHZ state].
AI frequently miscalculates qubit index order or fails to apply conditional Pauli-X to the second superposition branch.
EXT_010
Complex Cryptographic Protocol State Machine
Extreme
In an OAuth 2.0 PKCE flow, the client generates a code_verifier 'X'. It computes code_challenge = Base64URL(SHA256('X')). An attacker intercepts the Authorization Code and attempts to exchange it at the token endpoint by providing Base64URL(SHA256('X')) as the code_verifier. What error code does the Authorization Serve...
invalid_grant
1. Server hashes incoming verifier: HASH(HASH(X)) != code_challenge HASH(X). 2. Verification fails. RFC 7636 Section 4.6 mandates HTTP 400 with error 'invalid_grant'.
AI often guesses 'invalid_request' or 'unauthorized_client' instead of RFC-specified 'invalid_grant'.

Master Extreme LLM Benchmark (B2B Evaluation Dataset)

A specialized benchmark dataset designed to test frontier LLMs on complex edge-cases, dynamic multi-step logic, and failure modes that standard benchmarks miss.

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