//! Test Vector Validation
//!
//! Validates that our implementation produces byte-exact output matching
//! the test vectors in docs/spec/test-vectors.md
//!
//! These tests ensure the specification and implementation stay in sync.

use std::collections::BTreeMap;
use tenuo::*;

// Fixed timestamps from spec (2024-01-01T00:00:00Z and +1 hour)
const ISSUED_AT: u64 = 1704067200;
const EXPIRES_AT: u64 = 1704070800;

// Future timestamps for tests that need to verify against live verifier
// (2030-01-01T00:00:00Z and +1 hour)
const FUTURE_ISSUED_AT: u64 = 1893456000;
const FUTURE_EXPIRES_AT: u64 = 1893459600;

// Fixed warrant IDs (deterministic UUIDs from spec)
const ID_A1: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x01,
];
const ID_A3_L0: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x10,
];
const ID_A3_L1: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x11,
];
const ID_A3_L2: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x12,
];
const ID_A5: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x50,
];
const ID_A6: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x60,
];
const ID_A7: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x70,
];
const ID_A10_PARENT: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x90,
];
const ID_A10_CHILD: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x91,
];
const ID_A11_PARENT: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x92,
];
const ID_A11_CHILD: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x93,
];
const ID_A12_PARENT: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xA0,
];
const ID_A12_CHILD: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xA1,
];
const ID_A13_PARENT: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xB0,
];
const ID_A13_CHILD: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xB1,
];
const ID_A14: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xC0,
];
const ID_A15_ISSUER: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xD0,
];
const ID_A15_CHILD: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xD1,
];
// A.16 uses builder API (not raw payload), so ID not needed
#[allow(dead_code)]
const ID_A16: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xE0,
];
const ID_A17_PARENT: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xF0,
];
const ID_A17_CHILD: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0xF1,
];
const ID_A18: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x18,
];
// A.2 uses builder API (not raw payload), so ID not needed
#[allow(dead_code)]
const ID_A2: [u8; 16] = [
    0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00, 0x02,
];

// Fixed seeds for deterministic key generation (from spec)
fn control_plane_key() -> SigningKey {
    SigningKey::from_bytes(&[0x01; 32])
}

fn orchestrator_key() -> SigningKey {
    SigningKey::from_bytes(&[0x02; 32])
}

fn worker_key() -> SigningKey {
    SigningKey::from_bytes(&[0x03; 32])
}

fn worker2_key() -> SigningKey {
    SigningKey::from_bytes(&[0x04; 32])
}

fn attacker_key() -> SigningKey {
    SigningKey::from_bytes(&[0xFF; 32])
}

// Test vector nonce for A.24 SignedApproval - deterministic for byte-exact interop testing
const TEST_VECTOR_NONCE: [u8; 16] = [
    0xA1, 0xA2, 0xA3, 0xA4, 0xA5, 0xA6, 0xA7, 0xA8, 0xB1, 0xB2, 0xB3, 0xB4, 0xB5, 0xB6, 0xB7, 0xB8,
];

/// Test Vector A.1: Minimal Valid Execution Warrant
#[test]
fn test_vector_a1_minimal_execution_warrant() {
    // Expected bytes from docs/spec/test-vectors.md A.1
    let expected_payload_hex = "\
aa00010150019471f8000070008000000000000001020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688210f604820158208139\
770ea87d175f56a35466c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b3940582\
0158208a88e3dd7409f195fd52db2d3cba5d72ca6709bf1d94121bf3748801b4\
0f6f5c061a65920080071a65920e9008031200";

    let expected_sig_hex = "\
4396783e89f37eebfa7d25ad7d61d6cddfbb6c58eade0e9ccc6e28759f1eb56b\
3c03873a6232483d05f766481edf9f85560881aed03b6ef25771285409e6d800";

    // Regenerate the warrant
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();

    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert("path".to_string(), Constraint::Wildcard(Wildcard));
    tools.insert("read_file".to_string(), cs);

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A1),
        tools,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant = sign_payload(&payload, &control_plane);

    // Verify byte-exact match
    assert_eq!(
        hex::encode(warrant.payload_bytes()),
        expected_payload_hex,
        "A.1 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant.signature().to_bytes()),
        expected_sig_hex,
        "A.1 signature mismatch"
    );
}

/// Test Vector A.3 Level 0: 3-Level Chain Root
#[test]
fn test_vector_a3_level0_chain_root() {
    let expected_payload_hex = "\
aa00010150019471f8000070008000000000000010020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e672f646174612f2a04820158208139770ea87d175f56a35466c34c7ecccb8d\
8a91b4ee37a25df60f5b8fc9b39405820158208a88e3dd7409f195fd52db2d3c\
ba5d72ca6709bf1d94121bf3748801b40f6f5c061a65920080071a65920e9008\
031200";

    let expected_sig_hex = "\
98bcd71626112aded9d4d1aa728580934d908611ea15fb90a44b4efb00ad5114\
5dbe1c5ee1b2ba5790bc1215bd9805b2b06449b271f5a8fd080564cba2335a09";

    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();

    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools.insert("read_file".to_string(), cs);

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L0),
        tools,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant = sign_payload(&payload, &control_plane);

    assert_eq!(
        hex::encode(warrant.payload_bytes()),
        expected_payload_hex,
        "A.3 Level 0 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant.signature().to_bytes()),
        expected_sig_hex,
        "A.3 Level 0 signature mismatch"
    );
}

/// Test Vector A.3 Level 1: First Attenuation
#[test]
fn test_vector_a3_level1_first_attenuation() {
    let expected_payload_hex = "\
ab00010150019471f8000070008000000000000011020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e6f2f646174612f7265706f7274732f2a0482015820ed4928c628d1c2c6eae9\
0338905995612959273a5c63f93636c14614ac8737d105820158208139770ea8\
7d175f56a35466c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b394061a659200\
80071a65920e9008030998201870185e187918411868182318ef1881189a0818\
e018c5189f18ec18cb185d184b18ae18d418a718eb18ca18ca18290b01184112\
18ce18c518fc18641201";

    let expected_sig_hex = "\
a3ec5b753afad510ffa1145ce686f930470976dd93b5da08a6bf26fdaaac60d7\
c3420d5c87021fe63713e06f1a2a60360dea7f3776a0f28da0bb3d42c3319906";

    // Need Level 0 parent for parent_hash
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Build Level 0
    let mut tools_l0 = BTreeMap::new();
    let mut cs_l0 = ConstraintSet::new();
    cs_l0.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_l0.insert("read_file".to_string(), cs_l0);

    let payload_l0 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L0),
        tools: tools_l0,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l0 = sign_payload(&payload_l0, &control_plane);
    let parent_hash_l1 = sha256(warrant_l0.payload_bytes());

    // Build Level 1
    let mut tools_l1 = BTreeMap::new();
    let mut cs_l1 = ConstraintSet::new();
    cs_l1.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_l1.insert("read_file".to_string(), cs_l1);

    let payload_l1 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L1),
        tools: tools_l1,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash_l1),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l1 = sign_payload(&payload_l1, &orchestrator);

    assert_eq!(
        hex::encode(warrant_l1.payload_bytes()),
        expected_payload_hex,
        "A.3 Level 1 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant_l1.signature().to_bytes()),
        expected_sig_hex,
        "A.3 Level 1 signature mismatch"
    );
}

/// Test Vector A.3 Level 2: Most Restricted
#[test]
fn test_vector_a3_level2_most_restricted() {
    let expected_payload_hex = "\
ab00010150019471f8000070008000000000000012020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688201a16576616c756574\
2f646174612f7265706f7274732f71332e7064660482015820ca93ac17051870\
71d67b83c7ff0efe8108e8ec4530575d7726879333dbdabe7c0582015820ed49\
28c628d1c2c6eae90338905995612959273a5c63f93636c14614ac8737d1061a\
65920080071a65920e900803099820184a189418bb18941877181e184e18d418\
4c18c40a18cb187f188b01186418cd18b00818af1894188c18b1189518900618\
3718ff186e189818f9189b1202";

    let expected_sig_hex = "\
f47307c756b98144fd4eeac30c157e317a307da7630db619001f531c479128fd\
1997c666baf0d020e8d60619bb8644f79a5a0038836d49b2a1f676fc7ee8d307";

    // Build full chain to get correct parent_hash
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();
    let worker2 = worker2_key();

    // Level 0
    let mut tools_l0 = BTreeMap::new();
    let mut cs_l0 = ConstraintSet::new();
    cs_l0.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_l0.insert("read_file".to_string(), cs_l0);

    let payload_l0 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L0),
        tools: tools_l0,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l0 = sign_payload(&payload_l0, &control_plane);
    let parent_hash_l1 = sha256(warrant_l0.payload_bytes());

    // Level 1
    let mut tools_l1 = BTreeMap::new();
    let mut cs_l1 = ConstraintSet::new();
    cs_l1.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_l1.insert("read_file".to_string(), cs_l1);

    let payload_l1 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L1),
        tools: tools_l1,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash_l1),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l1 = sign_payload(&payload_l1, &orchestrator);
    let parent_hash_l2 = sha256(warrant_l1.payload_bytes());

    // Level 2
    let mut tools_l2 = BTreeMap::new();
    let mut cs_l2 = ConstraintSet::new();
    cs_l2.insert(
        "path".to_string(),
        Constraint::Exact(Exact::new("/data/reports/q3.pdf")),
    );
    tools_l2.insert("read_file".to_string(), cs_l2);

    let payload_l2 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L2),
        tools: tools_l2,
        holder: worker2.public_key(),
        issuer: worker.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 2,
        parent_hash: Some(parent_hash_l2),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l2 = sign_payload(&payload_l2, &worker);

    assert_eq!(
        hex::encode(warrant_l2.payload_bytes()),
        expected_payload_hex,
        "A.3 Level 2 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant_l2.signature().to_bytes()),
        expected_sig_hex,
        "A.3 Level 2 signature mismatch"
    );
}

/// Test Vector A.5: Expired Warrant
#[test]
fn test_vector_a5_expired_warrant() {
    let expected_payload_hex = "\
aa00010150019471f8000070008000000000000050020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688210f604820158208139\
770ea87d175f56a35466c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b3940582\
0158208a88e3dd7409f195fd52db2d3cba5d72ca6709bf1d94121bf3748801b4\
0f6f5c061a65920080071a6592008108031200";

    let expected_sig_hex = "\
13c824cd5c27c5fc1b6c0fd36ed0579d3278a1dd8df2b5e941679e25890f3129\
530dfd1ba49d4691bbb56aa30f4eafdeea15e60a4f20c61c56bcf888404f4f0a";

    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();

    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert("path".to_string(), Constraint::Wildcard(Wildcard));
    tools.insert("read_file".to_string(), cs);

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A5),
        tools,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: ISSUED_AT + 1, // 1 second TTL
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant = sign_payload(&payload, &control_plane);

    assert_eq!(
        hex::encode(warrant.payload_bytes()),
        expected_payload_hex,
        "A.5 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant.signature().to_bytes()),
        expected_sig_hex,
        "A.5 signature mismatch"
    );

    // Verify it's actually expired
    assert!(
        warrant.is_expired(),
        "A.5 warrant should be expired (TTL was 1 second)"
    );
}

/// Test Vector A.6: Proof-of-Possession
#[test]
fn test_vector_a6_proof_of_possession() {
    let expected_payload_hex = "\
aa00010150019471f8000070008000000000000060020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688201a16576616c756570\
2f646174612f7265706f72742e7064660482015820ed4928c628d1c2c6eae903\
38905995612959273a5c63f93636c14614ac8737d105820158208a88e3dd7409\
f195fd52db2d3cba5d72ca6709bf1d94121bf3748801b40f6f5c061a65920080\
071a65920e9008011200";

    let expected_sig_hex = "\
3c170967a561d9bf81c4d45398fa6defdddfcb87157bde9e597a7e16abca5c22\
6b31199e57ca87953ce814a178c6e018835c8a24c50afbc4bcdc8d485a9d5a0c";

    let expected_pop_sig_hex = "\
84f11618ec5b7234287e3fc1dbb6f8c18de9aab1ad60d8bc3e26ba293814a062\
0cae3be2c96baf7698ef959105231d2b4eee57fa247a56c11170d100e66d6f0a";

    let control_plane = control_plane_key();
    let worker = worker_key();

    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert(
        "path".to_string(),
        Constraint::Exact(Exact::new("/data/report.pdf")),
    );
    tools.insert("read_file".to_string(), cs);

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A6),
        tools,
        holder: worker.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 1,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant = sign_payload(&payload, &control_plane);

    assert_eq!(
        hex::encode(warrant.payload_bytes()),
        expected_payload_hex,
        "A.6 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant.signature().to_bytes()),
        expected_sig_hex,
        "A.6 signature mismatch"
    );

    // Generate PoP signature
    const POP_CONTEXT: &[u8] = b"tenuo-pop-v1";
    const POP_TIMESTAMP_WINDOW: i64 = (ISSUED_AT as i64 / 30) * 30;

    let pop_challenge = (
        warrant.id().to_string(),
        "read_file".to_string(),
        vec![("path".to_string(), "/data/report.pdf".to_string())],
        POP_TIMESTAMP_WINDOW,
    );

    let mut challenge_bytes = Vec::new();
    ciborium::ser::into_writer(&pop_challenge, &mut challenge_bytes)
        .expect("Failed to serialize challenge");

    let mut pop_preimage = Vec::new();
    pop_preimage.extend_from_slice(POP_CONTEXT);
    pop_preimage.extend_from_slice(&challenge_bytes);

    let pop_signature = worker.sign(&pop_preimage);

    assert_eq!(
        hex::encode(pop_signature.to_bytes()),
        expected_pop_sig_hex,
        "A.6 PoP signature mismatch"
    );

    // Verify PoP signature
    assert!(
        worker
            .public_key()
            .verify(&pop_preimage, &pop_signature)
            .is_ok(),
        "A.6 PoP signature should verify"
    );
}

/// Test Vector A.2: Minimal Issuer Warrant
#[test]
fn test_vector_a2_minimal_issuer_warrant() {
    const ID_A2: [u8; 16] = [
        0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00,
        0x02,
    ];

    let expected_payload_hex = "\
ac00010150019471f8000070008000000000000002020103a004820158208139\
770ea87d175f56a35466c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b3940582\
0158208a88e3dd7409f195fd52db2d3cba5d72ca6709bf1d94121bf3748801b4\
0f6f5c061a65920080071a65920e9008050b8269726561645f66696c656a7772\
6974655f66696c650d031200";

    let expected_sig_hex = "\
a00345650d5ede861ee944a42012b8c7b9f8f7172a5f750e7c9bec592118b15e\
ffd554ec7c2d020c10bd38c37369104ae79d91e3acf8bd22b344ba8b1291d707";

    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Issuer,
        id: warrant::WarrantId::from_bytes(ID_A2),
        tools: BTreeMap::new(), // Issuer warrants have empty tools
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 5,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: Some(vec!["read_file".to_string(), "write_file".to_string()]),
        max_issue_depth: Some(3),
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant = sign_payload(&payload, &control_plane);

    assert_eq!(
        hex::encode(warrant.payload_bytes()),
        expected_payload_hex,
        "A.2 payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(warrant.signature().to_bytes()),
        expected_sig_hex,
        "A.2 signature mismatch"
    );

    // Verify it's an issuer warrant
    assert_eq!(
        warrant.r#type(),
        warrant::WarrantType::Issuer,
        "A.2 should be an Issuer warrant"
    );
}

/// Test Vector A.4: Invalid Chain (I1 Violation)
/// Verifies that chains with wrong issuer are properly detected
#[test]
fn test_vector_a4_invalid_chain_i1_violation() {
    const ID_A4: [u8; 16] = [
        0x01, 0x94, 0x71, 0xf8, 0x00, 0x00, 0x70, 0x00, 0x80, 0x00, 0x00, 0x00, 0x00, 0x00, 0x00,
        0x40,
    ];

    let expected_invalid_payload_hex = "\
ab00010150019471f8000070008000000000000040020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e672f646174612f2a0482015820ca93ac1705187071d67b83c7ff0efe8108e8\
ec4530575d7726879333dbdabe7c0582015820ed4928c628d1c2c6eae9033890\
5995612959273a5c63f93636c14614ac8737d1061a65920080071a65920e9008\
030998201870185e187918411868182318ef1881189a0818e018c5189f18ec18\
cb185d184b18ae18d418a718eb18ca18ca18290b0118411218ce18c518fc1864\
1201";

    let expected_invalid_sig_hex = "\
93d9c6d8a26fb450f9245c9cfec0a34dc8033bb08ed669d6f19502d1da0d35d5\
64b1a3767a2a469353417136ebc6ed9b27645b806c708baadc3dde27b4116f0c";

    // Build valid Level 0 (parent)
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();
    let worker2 = worker2_key();

    let mut tools_l0 = BTreeMap::new();
    let mut cs_l0 = ConstraintSet::new();
    cs_l0.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_l0.insert("read_file".to_string(), cs_l0);

    let payload_l0 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L0),
        tools: tools_l0.clone(),
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l0 = sign_payload(&payload_l0, &control_plane);
    let parent_hash = sha256(warrant_l0.payload_bytes());

    // Build INVALID child: signed by Worker (wrong), should be Orchestrator
    let payload_invalid = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A4),
        tools: tools_l0,
        holder: worker2.public_key(),
        issuer: worker.public_key(), // WRONG: Should be orchestrator (parent's holder)
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let invalid_warrant = sign_payload(&payload_invalid, &worker);

    // Verify byte-exact match with test vector
    assert_eq!(
        hex::encode(invalid_warrant.payload_bytes()),
        expected_invalid_payload_hex,
        "A.4 invalid payload bytes mismatch"
    );
    assert_eq!(
        hex::encode(invalid_warrant.signature().to_bytes()),
        expected_invalid_sig_hex,
        "A.4 invalid signature mismatch"
    );

    // Verify that the I1 invariant is violated:
    // child.issuer != parent.holder
    assert_ne!(
        invalid_warrant.issuer(),
        warrant_l0.authorized_holder(),
        "A.4 should demonstrate I1 violation: child.issuer != parent.holder"
    );
}

/// Test Vector A.8: WarrantStack Serialization
#[test]
fn test_vector_a8_warrant_stack_serialization() {
    // Expected WarrantStack CBOR (851 bytes) - first 64 hex chars for verification
    let expected_stack_prefix = "83830158a3aa00010150019471f8000070008000000000000010";

    // Build the full 3-level chain
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();
    let worker2 = worker2_key();

    // Level 0
    let mut tools_l0 = BTreeMap::new();
    let mut cs_l0 = ConstraintSet::new();
    cs_l0.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_l0.insert("read_file".to_string(), cs_l0);

    let payload_l0 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L0),
        tools: tools_l0,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l0 = sign_payload(&payload_l0, &control_plane);
    let parent_hash_l1 = sha256(warrant_l0.payload_bytes());

    // Level 1
    let mut tools_l1 = BTreeMap::new();
    let mut cs_l1 = ConstraintSet::new();
    cs_l1.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_l1.insert("read_file".to_string(), cs_l1);

    let payload_l1 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L1),
        tools: tools_l1,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash_l1),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l1 = sign_payload(&payload_l1, &orchestrator);
    let parent_hash_l2 = sha256(warrant_l1.payload_bytes());

    // Level 2
    let mut tools_l2 = BTreeMap::new();
    let mut cs_l2 = ConstraintSet::new();
    cs_l2.insert(
        "path".to_string(),
        Constraint::Exact(Exact::new("/data/reports/q3.pdf")),
    );
    tools_l2.insert("read_file".to_string(), cs_l2);

    let payload_l2 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A3_L2),
        tools: tools_l2,
        holder: worker2.public_key(),
        issuer: worker.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 2,
        parent_hash: Some(parent_hash_l2),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_l2 = sign_payload(&payload_l2, &worker);

    // Create WarrantStack as CBOR array
    let warrant_stack = vec![&warrant_l0, &warrant_l1, &warrant_l2];
    let mut stack_bytes = Vec::new();
    ciborium::ser::into_writer(&warrant_stack, &mut stack_bytes)
        .expect("Failed to serialize warrant stack");

    // Verify size (851 bytes per spec)
    assert_eq!(
        stack_bytes.len(),
        851,
        "A.8 WarrantStack should be 851 bytes"
    );

    // Verify prefix matches expected
    let stack_hex = hex::encode(&stack_bytes);
    assert!(
        stack_hex.starts_with(expected_stack_prefix),
        "A.8 WarrantStack prefix mismatch.\nExpected prefix: {}\nGot: {}",
        expected_stack_prefix,
        &stack_hex[..expected_stack_prefix.len().min(stack_hex.len())]
    );

    // Verify structure: outer array has 3 elements
    assert_eq!(stack_bytes[0], 0x83, "A.8 should start with array(3)");

    // Verify round-trip deserialization
    let deserialized: Vec<Warrant> =
        ciborium::de::from_reader(&stack_bytes[..]).expect("Failed to deserialize WarrantStack");
    assert_eq!(
        deserialized.len(),
        3,
        "A.8 should deserialize to 3 warrants"
    );

    // Verify chain invariants
    assert_eq!(
        deserialized[1].issuer(),
        deserialized[0].authorized_holder(),
        "A.8 Level 1 issuer should be Level 0 holder"
    );
    assert_eq!(
        deserialized[2].issuer(),
        deserialized[1].authorized_holder(),
        "A.8 Level 2 issuer should be Level 1 holder"
    );
}

/// Test Vector A.7: Extensions with CBOR Values
#[test]
fn test_vector_a7_extensions_with_cbor() {
    let expected_payload_hex = "\
ab00010150019471f8000070008000000000000070020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688201a16576616c756570\
2f646174612f7265706f72742e70646604820158208139770ea87d175f56a354\
66c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b39405820158208a88e3dd7409\
f195fd52db2d3cba5d72ca6709bf1d94121bf3748801b40f6f5c061a65920080\
071a65920e9008030aa273636f6d2e6578616d706c652e62696c6c696e679838\
18a31864187418651861186d186b186d186c182d187218651873186518611872\
18631868186718701872186f186a186518631874186e18771861187218721861\
186e1874182d18731879187318741865186d186b1863186f18731874185f1863\
1865186e187418651872181910186974636f6d2e6578616d706c652e74726163\
655f69648e186d1872186518711875186518731874182d183118321833183418\
351200";

    let expected_sig_hex = "\
e760545471300ee3493c16336d8013b3e815c34fb79179a490570a016d8a0347\
30f22302bded9573b8264d0700e85cd93fbf683ef4648973fa11ae63a50b5900";

    // Create keys (same seeds as generator)
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();

    // Create extensions with CBOR-encoded values
    let mut extensions = BTreeMap::new();

    // Extension 1: Simple string (CBOR-encoded)
    let trace_id = "request-12345";
    let mut trace_id_bytes = Vec::new();
    ciborium::ser::into_writer(&trace_id, &mut trace_id_bytes).expect("Failed to encode trace_id");
    extensions.insert("com.example.trace_id".to_string(), trace_id_bytes);

    // Extension 2: Structured data (CBOR-encoded)
    #[derive(serde::Serialize, serde::Deserialize, Debug, PartialEq)]
    struct BillingTag {
        team: String,
        project: String,
        cost_center: u32,
    }
    let billing = BillingTag {
        team: "ml-research".to_string(),
        project: "warrant-system".to_string(),
        cost_center: 4201,
    };
    let mut billing_bytes = Vec::new();
    ciborium::ser::into_writer(&billing, &mut billing_bytes).expect("Failed to encode billing");
    extensions.insert("com.example.billing".to_string(), billing_bytes);

    // Create payload
    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert(
        "path".to_string(),
        Constraint::Exact(Exact::new("/data/report.pdf")),
    );
    tools.insert("read_file".to_string(), cs);

    let payload_a7 = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A7),
        tools,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions,
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    // Sign payload
    let warrant_a7 = sign_payload(&payload_a7, &control_plane);

    // Verify byte-exact match
    assert_eq!(
        hex::encode(warrant_a7.payload_bytes()),
        expected_payload_hex,
        "A.7 payload bytes should match test vector"
    );
    assert_eq!(
        hex::encode(warrant_a7.signature().to_bytes()),
        expected_sig_hex,
        "A.7 signature should match test vector"
    );

    // Verify extensions round-trip
    let extensions_map = &warrant_a7.payload.extensions;
    assert_eq!(extensions_map.len(), 2, "A.7 should have 2 extensions");
    assert!(
        extensions_map.contains_key("com.example.trace_id"),
        "A.7 should have trace_id extension"
    );
    assert!(
        extensions_map.contains_key("com.example.billing"),
        "A.7 should have billing extension"
    );

    // Verify extension values decode correctly
    let trace_id_decoded: String =
        ciborium::de::from_reader(&extensions_map["com.example.trace_id"][..])
            .expect("Failed to decode trace_id");
    assert_eq!(
        trace_id_decoded, "request-12345",
        "A.7 trace_id should match"
    );

    let billing_decoded: BillingTag =
        ciborium::de::from_reader(&extensions_map["com.example.billing"][..])
            .expect("Failed to decode billing");
    assert_eq!(
        billing_decoded.team, "ml-research",
        "A.7 billing.team should match"
    );
    assert_eq!(
        billing_decoded.project, "warrant-system",
        "A.7 billing.project should match"
    );
    assert_eq!(
        billing_decoded.cost_center, 4201,
        "A.7 billing.cost_center should match"
    );

    // Verify CBOR hex encoding matches documented values
    let expected_trace_id_cbor = "6d726571756573742d3132333435";
    let expected_billing_cbor = "a3647465616d6b6d6c2d72657365617263686770726f6a6563746e77617272616e742d73797374656d6b636f73745f63656e746572191069";

    assert_eq!(
        hex::encode(&extensions_map["com.example.trace_id"]),
        expected_trace_id_cbor,
        "A.7 trace_id CBOR encoding should match"
    );
    assert_eq!(
        hex::encode(&extensions_map["com.example.billing"]),
        expected_billing_cbor,
        "A.7 billing CBOR encoding should match"
    );
}

/// Test Vector A.10: Invalid Depth Monotonicity (I2 Violation)
/// Uses future timestamps so verifier doesn't reject on expiration
#[test]
fn test_vector_a10_invalid_depth_monotonicity() {
    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Create parent warrant (depth=0) with FUTURE timestamps
    let mut tools_parent = BTreeMap::new();
    let mut cs_parent = ConstraintSet::new();
    cs_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_parent.insert("read_file".to_string(), cs_parent);

    let payload_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A10_PARENT),
        tools: tools_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_parent = sign_payload(&payload_parent, &control_plane);
    let parent_hash = sha256(warrant_parent.payload_bytes());

    // Create child with WRONG depth (2 instead of 1)
    let mut tools_child = BTreeMap::new();
    let mut cs_child = ConstraintSet::new();
    cs_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_child.insert("read_file".to_string(), cs_child);

    let payload_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A10_CHILD),
        tools: tools_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 2, // WRONG: should be 1
        parent_hash: Some(parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_child = sign_payload(&payload_child, &orchestrator);

    // Verify the depth violation
    assert_eq!(warrant_parent.payload.depth, 0, "A.10 parent depth");
    assert_eq!(warrant_child.payload.depth, 2, "A.10 child depth (wrong)");
    assert_ne!(
        warrant_child.payload.depth,
        warrant_parent.payload.depth + 1,
        "A.10 child should have WRONG depth (I2 violation)"
    );

    // Verify that the verifier REJECTS this chain
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant_parent, warrant_child]);
    assert!(
        result.is_err(),
        "A.10 verify_chain should REJECT depth violation"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("depth") || err_msg.contains("Depth"),
        "A.10 error should mention depth: {}",
        err_msg
    );
}

/// Test Vector A.11: Invalid Capability Monotonicity (I4 Violation)
/// Uses future timestamps so verifier doesn't reject on expiration
#[test]
fn test_vector_a11_invalid_capability_monotonicity() {
    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Create parent warrant with NARROW constraint
    let mut tools_parent = BTreeMap::new();
    let mut cs_parent = ConstraintSet::new();
    cs_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()), // Narrow
    );
    tools_parent.insert("read_file".to_string(), cs_parent);

    let payload_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A11_PARENT),
        tools: tools_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_parent = sign_payload(&payload_parent, &control_plane);
    let parent_hash = sha256(warrant_parent.payload_bytes());

    // Create child with BROADER constraint (invalid!)
    let mut tools_child = BTreeMap::new();
    let mut cs_child = ConstraintSet::new();
    cs_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()), // TOO BROAD!
    );
    tools_child.insert("read_file".to_string(), cs_child);

    let payload_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A11_CHILD),
        tools: tools_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_child = sign_payload(&payload_child, &orchestrator);

    // Verify that the verifier REJECTS this chain
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant_parent, warrant_child]);
    assert!(
        result.is_err(),
        "A.11 verify_chain should REJECT capability expansion"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("attenuation")
            || err_msg.contains("Pattern")
            || err_msg.contains("expand"),
        "A.11 error should mention attenuation/pattern issue: {}",
        err_msg
    );
}

/// Test Vector A.12: Invalid Parent Hash (I5 Violation)
#[test]
fn test_vector_a12_invalid_parent_hash() {
    // Parent warrant
    let expected_parent_payload_hex = "\
aa00010150019471f80000700080000000000000a0020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e672f646174612f2a04820158208139770ea87d175f56a35466c34c7ecccb8d\
8a91b4ee37a25df60f5b8fc9b39405820158208a88e3dd7409f195fd52db2d3c\
ba5d72ca6709bf1d94121bf3748801b40f6f5c061a65920080071a65920e9008\
031200";

    let expected_parent_sig_hex = "\
795cfa2f604317b61c770a2e1595968be9fc9ff77846b9c65f1e40570eb17344\
b62d8929ddc1ac1af2a40f1f9a0d817057f2a397a609afeb581e24ca1cb79f0c";

    // Child warrant with WRONG parent hash
    let expected_child_payload_hex = "\
ab00010150019471f80000700080000000000000a1020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e6f2f646174612f7265706f7274732f2a0482015820ed4928c628d1c2c6eae9\
0338905995612959273a5c63f93636c14614ac8737d105820158208139770ea8\
7d175f56a35466c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b394061a659200\
80071a65920e9008030998200000000000000000000000000000000000000000\
0000000000000000000000001201";

    let expected_child_sig_hex = "\
65cc4fc544c331ba682404a444367d644ebd4438a8e731eb84c0f1d0ba575955\
68e94fb3053a20d22727770414f5b7c9f2f7c32841801ec93c07bd842ac9490b";

    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Create parent warrant
    let mut tools_parent = BTreeMap::new();
    let mut cs_parent = ConstraintSet::new();
    cs_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_parent.insert("read_file".to_string(), cs_parent);

    let payload_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A12_PARENT),
        tools: tools_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_parent = sign_payload(&payload_parent, &control_plane);

    // Verify parent matches
    assert_eq!(
        hex::encode(warrant_parent.payload_bytes()),
        expected_parent_payload_hex,
        "A.12 parent payload bytes should match"
    );
    assert_eq!(
        hex::encode(warrant_parent.signature().to_bytes()),
        expected_parent_sig_hex,
        "A.12 parent signature should match"
    );

    // Create child with WRONG parent hash (all zeros)
    let wrong_parent_hash = [0u8; 32];
    let correct_parent_hash = sha256(warrant_parent.payload_bytes());

    let mut tools_child = BTreeMap::new();
    let mut cs_child = ConstraintSet::new();
    cs_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_child.insert("read_file".to_string(), cs_child);

    let payload_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A12_CHILD),
        tools: tools_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(wrong_parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_child = sign_payload(&payload_child, &orchestrator);

    // Verify child matches
    assert_eq!(
        hex::encode(warrant_child.payload_bytes()),
        expected_child_payload_hex,
        "A.12 child payload bytes should match"
    );
    assert_eq!(
        hex::encode(warrant_child.signature().to_bytes()),
        expected_child_sig_hex,
        "A.12 child signature should match"
    );

    // Verify the hash comparison
    assert_eq!(
        hex::encode(correct_parent_hash),
        "9b60b7ae1a679d990d77502db310315455d3b624f9a616f5bb7f34bccbd37914",
        "A.12 correct parent hash should match"
    );
    assert_eq!(
        hex::encode(wrong_parent_hash),
        "0000000000000000000000000000000000000000000000000000000000000000",
        "A.12 wrong parent hash should be all zeros"
    );
    assert_ne!(
        warrant_child.payload.parent_hash.unwrap(),
        correct_parent_hash,
        "A.12 child should have WRONG parent hash (I5 violation)"
    );

    // Create fresh warrants with FUTURE timestamps for verifier rejection test
    // (the byte-exact test above uses historical timestamps from the spec)
    let mut tools_verify_parent = BTreeMap::new();
    let mut cs_verify_parent = ConstraintSet::new();
    cs_verify_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_verify_parent.insert("read_file".to_string(), cs_verify_parent);

    let payload_verify_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A12_PARENT),
        tools: tools_verify_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_verify_parent = sign_payload(&payload_verify_parent, &control_plane);
    let wrong_hash = [0u8; 32]; // Wrong hash

    let mut tools_verify_child = BTreeMap::new();
    let mut cs_verify_child = ConstraintSet::new();
    cs_verify_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_verify_child.insert("read_file".to_string(), cs_verify_child);

    let payload_verify_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A12_CHILD),
        tools: tools_verify_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(wrong_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_verify_child = sign_payload(&payload_verify_child, &orchestrator);

    // Verify that the verifier REJECTS this chain
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant_verify_parent, warrant_verify_child]);
    assert!(
        result.is_err(),
        "A.12 verify_chain should REJECT parent hash mismatch"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("hash") || err_msg.contains("broken"),
        "A.12 error should mention hash mismatch: {}",
        err_msg
    );
}

/// Test Vector A.13: TTL Extension Attack (I3 Violation)
#[test]
fn test_vector_a13_ttl_extension_attack() {
    // Parent warrant
    let expected_parent_payload_hex = "\
aa00010150019471f80000700080000000000000b0020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e672f646174612f2a04820158208139770ea87d175f56a35466c34c7ecccb8d\
8a91b4ee37a25df60f5b8fc9b39405820158208a88e3dd7409f195fd52db2d3c\
ba5d72ca6709bf1d94121bf3748801b40f6f5c061a65920080071a65920e9008\
031200";

    let expected_parent_sig_hex = "\
221a7bcbe2e9427338c316262d2322edfcc59340814447b0deaf5556dd11ff76\
4ca48a4166aedafa21da6a52e22d9b0b20392ad425c10eaad4221157f730e903";

    // Child warrant with EXTENDED TTL
    let expected_child_payload_hex = "ab00010150019471f80000700080000000000000b1020003a169726561645f66696c65a16b636f6e73747261696e7473a164706174688202a1677061747465726e6f2f646174612f7265706f7274732f2a0482015820ed4928c628d1c2c6eae90338905995612959273a5c63f93636c14614ac8737d105820158208139770ea87d175f56a35466c34c7ecccb8d8a91b4ee37a25df60f5b8fc9b394061a65920080071a65921ca0080309982018ee18451836184a1844184e18b40f183418b01718d81858184b18431856182918de18251882081862184a188d18e418fc18e618d318eb18d918a318c91201";

    let expected_child_sig_hex = "4cc40a8fb7776042dbc0eef0a4833c92b678b3da405d249c58226db34c26e1905f86f2e73e98d891e93d0cd79a1ab3b15d811b4d4cf5f3f6a6d06e8030e8f705";

    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Create parent warrant
    let mut tools_parent = BTreeMap::new();
    let mut cs_parent = ConstraintSet::new();
    cs_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_parent.insert("read_file".to_string(), cs_parent);

    let payload_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A13_PARENT),
        tools: tools_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT, // 1704070800
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_parent = sign_payload(&payload_parent, &control_plane);

    // Verify parent matches
    assert_eq!(
        hex::encode(warrant_parent.payload_bytes()),
        expected_parent_payload_hex,
        "A.13 parent payload bytes should match"
    );
    assert_eq!(
        hex::encode(warrant_parent.signature().to_bytes()),
        expected_parent_sig_hex,
        "A.13 parent signature should match"
    );

    // Create child with EXTENDED TTL (parent + 1 hour)
    let parent_hash = sha256(warrant_parent.payload_bytes());
    let extended_expires_at = EXPIRES_AT + 3600; // 1704074400

    let mut tools_child = BTreeMap::new();
    let mut cs_child = ConstraintSet::new();
    cs_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_child.insert("read_file".to_string(), cs_child);

    let payload_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A13_CHILD),
        tools: tools_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: ISSUED_AT,
        expires_at: extended_expires_at, // EXTENDED (invalid)
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_child = sign_payload(&payload_child, &orchestrator);

    // Verify child matches
    assert_eq!(
        hex::encode(warrant_child.payload_bytes()),
        expected_child_payload_hex,
        "A.13 child payload bytes should match"
    );
    assert_eq!(
        hex::encode(warrant_child.signature().to_bytes()),
        expected_child_sig_hex,
        "A.13 child signature should match"
    );

    // Verify TTL violation
    assert_eq!(
        warrant_parent.payload.expires_at, EXPIRES_AT,
        "A.13 parent expires_at"
    );
    assert_eq!(
        warrant_child.payload.expires_at, extended_expires_at,
        "A.13 child expires_at"
    );
    assert!(
        warrant_child.payload.expires_at > warrant_parent.payload.expires_at,
        "A.13 child should have EXTENDED TTL (I3 violation)"
    );

    // Create fresh warrants with FUTURE timestamps for verifier rejection test
    // (the byte-exact test above uses historical timestamps from the spec)
    let mut tools_verify_parent = BTreeMap::new();
    let mut cs_verify_parent = ConstraintSet::new();
    cs_verify_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_verify_parent.insert("read_file".to_string(), cs_verify_parent);

    let payload_verify_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A13_PARENT),
        tools: tools_verify_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_verify_parent = sign_payload(&payload_verify_parent, &control_plane);
    let verify_parent_hash = sha256(warrant_verify_parent.payload_bytes());
    let verify_extended_expires_at = FUTURE_EXPIRES_AT + 3600; // Extended by 1 hour

    let mut tools_verify_child = BTreeMap::new();
    let mut cs_verify_child = ConstraintSet::new();
    cs_verify_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/reports/*").unwrap()),
    );
    tools_verify_child.insert("read_file".to_string(), cs_verify_child);

    let payload_verify_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A13_CHILD),
        tools: tools_verify_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: verify_extended_expires_at, // EXTENDED (invalid)
        max_depth: 3,
        depth: 1,
        parent_hash: Some(verify_parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_verify_child = sign_payload(&payload_verify_child, &orchestrator);

    // Verify that the verifier REJECTS this chain
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant_verify_parent, warrant_verify_child]);
    assert!(
        result.is_err(),
        "A.13 verify_chain should REJECT TTL extension"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("expir") || err_msg.contains("TTL") || err_msg.contains("lifetime"),
        "A.13 error should mention expiration/TTL issue: {}",
        err_msg
    );
}

/// Test Vector A.14: Invalid Signature (Cryptographic Verification)
/// Tests that implementations correctly verify Ed25519 signatures
#[test]
fn test_vector_a14_invalid_signature() {
    // Expected hex values from generated test vectors
    let expected_forged_payload_hex = "\
aa00010150019471f80000700080000000000000c0020003a169726561645f66\
696c65a16b636f6e73747261696e7473a164706174688202a167706174746572\
6e672f646174612f2a04820158208139770ea87d175f56a35466c34c7ecccb8d\
8a91b4ee37a25df60f5b8fc9b39405820158208a88e3dd7409f195fd52db2d3c\
ba5d72ca6709bf1d94121bf3748801b40f6f5c061a65920080071a65920e9008\
031200";

    // Forged signature (signed by attacker key, not control_plane)
    let expected_forged_sig_hex = "\
0038e4fc6d200a00e3a39987a0e172d8086812331da17e911e0fc2699bde94a7\
e413ad1b7a2ea1886627d822535ab3f469cd43e7f28e4c7c476bede22dcc8a05";

    // Valid signature (signed by control_plane)
    let expected_valid_sig_hex = "\
8e08644ea750b3b09f8593b05fbb9f4d2c1c0b37f07dfe097fb58952ba279228\
eede73926d6d4d2796a2fdf69b28501aaa75439ebcbbd2adb9efd0f04bd84c0e";

    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let attacker = attacker_key();

    // Create warrant payload that CLAIMS to be issued by control_plane
    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools.insert("read_file".to_string(), cs);

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A14),
        tools,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(), // Claims to be from control_plane
        issued_at: ISSUED_AT,
        expires_at: EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    // Sign with WRONG key (attacker) - this should be rejected
    let warrant_forged = sign_payload(&payload, &attacker);

    // Sign with CORRECT key (control_plane) - this should be accepted
    let warrant_valid = sign_payload(&payload, &control_plane);

    // Verify payload bytes are IDENTICAL
    assert_eq!(
        warrant_forged.payload_bytes(),
        warrant_valid.payload_bytes(),
        "A.14 forged and valid should have identical payload bytes"
    );

    // Verify byte-exact match for forged warrant
    assert_eq!(
        hex::encode(warrant_forged.payload_bytes()),
        expected_forged_payload_hex,
        "A.14 forged payload bytes should match"
    );
    assert_eq!(
        hex::encode(warrant_forged.signature().to_bytes()),
        expected_forged_sig_hex,
        "A.14 forged signature should match"
    );

    // Verify byte-exact match for valid warrant
    assert_eq!(
        hex::encode(warrant_valid.signature().to_bytes()),
        expected_valid_sig_hex,
        "A.14 valid signature should match"
    );

    // Verify the forged warrant has the claimed issuer but different signer
    assert_eq!(
        warrant_forged.payload.issuer,
        control_plane.public_key(),
        "A.14 forged warrant claims to be from control_plane"
    );
    assert_ne!(
        attacker.public_key(),
        control_plane.public_key(),
        "A.14 attacker key should differ from control_plane"
    );

    // Create fresh warrants with FUTURE timestamps for verifier rejection test
    let mut tools_verify = BTreeMap::new();
    let mut cs_verify = ConstraintSet::new();
    cs_verify.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_verify.insert("read_file".to_string(), cs_verify);

    let payload_verify = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A14),
        tools: tools_verify,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_verify_forged = sign_payload(&payload_verify, &attacker);
    let warrant_verify_valid = sign_payload(&payload_verify, &control_plane);

    // Verify that the verifier REJECTS the forged warrant
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result_forged = data_plane.verify_chain(&[warrant_verify_forged]);
    assert!(
        result_forged.is_err(),
        "A.14 verify_chain should REJECT forged signature"
    );
    let err_msg = result_forged.unwrap_err().to_string();
    assert!(
        err_msg.contains("ignature") || err_msg.contains("verification"),
        "A.14 error should mention signature issue: {}",
        err_msg
    );

    // Verify that the verifier ACCEPTS the valid warrant
    let result_valid = data_plane.verify_chain(&[warrant_verify_valid]);
    assert!(
        result_valid.is_ok(),
        "A.14 verify_chain should ACCEPT valid signature: {:?}",
        result_valid.err()
    );
}

/// Test Vector A.15: Issuer Constraint Violation
/// Child warrant exceeds constraint bounds defined by issuer warrant
#[test]
fn test_vector_a15_issuer_constraint_violation() {
    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Create issuer warrant with constraint bounds limiting to /data/*
    let mut constraint_bounds = ConstraintSet::new();
    constraint_bounds.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );

    let payload_issuer = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Issuer,
        id: warrant::WarrantId::from_bytes(ID_A15_ISSUER),
        tools: BTreeMap::new(), // Issuer warrants have empty tools
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 5,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: Some(vec!["read_file".to_string()]),
        max_issue_depth: Some(3),
        constraint_bounds: Some(constraint_bounds),
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_issuer = sign_payload(&payload_issuer, &control_plane);
    let parent_hash = sha256(warrant_issuer.payload_bytes());

    // Create child execution warrant that EXCEEDS bounds (/etc/passwd is outside /data/*)
    let mut tools_child = BTreeMap::new();
    let mut cs_child = ConstraintSet::new();
    cs_child.insert(
        "path".to_string(),
        Constraint::Exact(Exact::new("/etc/passwd")), // OUTSIDE /data/* bounds!
    );
    tools_child.insert("read_file".to_string(), cs_child);

    let payload_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A15_CHILD),
        tools: tools_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_child = sign_payload(&payload_child, &orchestrator);

    // Verify that the verifier REJECTS this chain
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant_issuer, warrant_child]);
    assert!(
        result.is_err(),
        "A.15 verify_chain should REJECT constraint violation"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("bound")
            || err_msg.contains("constraint")
            || err_msg.contains("attenuation")
            || err_msg.contains("allowed"),
        "A.15 error should mention constraint bounds issue: {}",
        err_msg
    );
}

/// Test Vector A.16: Self-Issuance Violation
/// Tests that the Issuer → Execution self-issuance is blocked.
///
/// **Security rationale:** The holder of an Issuer warrant cannot issue an Execution
/// warrant to themselves. This enforces the separation of duties principle (P-LLM ≠ Q-LLM):
/// the entity that plans/issues warrants should not be the same entity that executes them.
///
/// **Note:** Self-issuance in Execution → Execution chains is NOT blocked because
/// monotonicity invariants (I2-I4) ensure it can only attenuate, never escalate capabilities.
#[test]
fn test_vector_a16_self_issuance_violation() {
    use std::time::Duration;

    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();

    // Create issuer warrant held by orchestrator
    let issuer_warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Issuer)
        .issuable_tools(vec!["read_file".to_string()])
        .ttl(Duration::from_secs(3600))
        .holder(orchestrator.public_key())
        .build(&control_plane)
        .expect("Failed to build issuer warrant");

    // Attempt self-issuance: orchestrator tries to issue execution warrant to themselves
    let self_issue_result = issuer_warrant
        .issue_execution_warrant()
        .unwrap()
        .capability("read_file", ConstraintSet::new())
        .ttl(Duration::from_secs(60))
        .holder(orchestrator.public_key()) // Same as issuer warrant holder!
        .build(&orchestrator);

    // Verify the builder REJECTS self-issuance
    assert!(
        self_issue_result.is_err(),
        "A.16 builder should REJECT Issuer → Execution self-issuance"
    );
    let err_msg = self_issue_result.unwrap_err().to_string();
    assert!(
        err_msg.contains("self") || err_msg.contains("Self") || err_msg.contains("issuance"),
        "A.16 error should mention self-issuance: {}",
        err_msg
    );
}

/// Test Vector A.17: Clearance Violation
/// Child attempts to increase clearance level beyond parent's
#[test]
fn test_vector_a17_clearance_violation() {
    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Create parent warrant with clearance=5
    let mut tools_parent = BTreeMap::new();
    let mut cs_parent = ConstraintSet::new();
    cs_parent.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_parent.insert("read_file".to_string(), cs_parent);

    let payload_parent = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A17_PARENT),
        tools: tools_parent,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: Some(Clearance(5)), // Parent clearance = 5
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_parent = sign_payload(&payload_parent, &control_plane);
    let parent_hash = sha256(warrant_parent.payload_bytes());

    // Create child with HIGHER clearance (invalid!)
    let mut tools_child = BTreeMap::new();
    let mut cs_child = ConstraintSet::new();
    cs_child.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools_child.insert("read_file".to_string(), cs_child);

    let payload_child = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A17_CHILD),
        tools: tools_child,
        holder: worker.public_key(),
        issuer: orchestrator.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 1,
        parent_hash: Some(parent_hash),
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: Some(Clearance(6)), // HIGHER than parent (invalid!)
        session_id: None,
        agent_id: None,
        required_approvers: None,
        min_approvals: None,
    };

    let warrant_child = sign_payload(&payload_child, &orchestrator);

    // Verify clearance violation
    assert_eq!(
        warrant_parent.payload.clearance,
        Some(Clearance(5)),
        "A.17 parent clearance should be 5"
    );
    assert_eq!(
        warrant_child.payload.clearance,
        Some(Clearance(6)),
        "A.17 child clearance should be 6"
    );
    assert!(
        warrant_child.payload.clearance > warrant_parent.payload.clearance,
        "A.17 child should have HIGHER clearance (violation)"
    );

    // Verify that the verifier REJECTS this chain
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant_parent, warrant_child]);
    assert!(
        result.is_err(),
        "A.17 verify_chain should REJECT clearance escalation"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("clearance")
            || err_msg.contains("Clearance")
            || err_msg.contains("escalat"),
        "A.17 error should mention clearance issue: {}",
        err_msg
    );
}

/// Test Vector A.18: Multi-sig Configuration
/// Warrant requires approvals from multiple parties
#[test]
fn test_vector_a18_multisig_configuration() {
    // Create keys
    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();
    let worker2 = worker2_key();

    // Create warrant with required approvers
    let mut tools = BTreeMap::new();
    let mut cs = ConstraintSet::new();
    cs.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );
    tools.insert("read_file".to_string(), cs);

    let payload = payload::WarrantPayload {
        version: 1,
        warrant_type: warrant::WarrantType::Execution,
        id: warrant::WarrantId::from_bytes(ID_A18),
        tools,
        holder: orchestrator.public_key(),
        issuer: control_plane.public_key(),
        issued_at: FUTURE_ISSUED_AT,
        expires_at: FUTURE_EXPIRES_AT,
        max_depth: 3,
        depth: 0,
        parent_hash: None,
        extensions: BTreeMap::new(),
        issuable_tools: None,
        max_issue_depth: None,
        constraint_bounds: None,
        clearance: None,
        session_id: None,
        agent_id: None,
        required_approvers: Some(vec![worker.public_key(), worker2.public_key()]),
        min_approvals: Some(1), // Require 1 of 2 approvers
    };

    let warrant = sign_payload(&payload, &control_plane);

    // Verify multi-sig configuration
    assert!(
        warrant.payload.required_approvers.is_some(),
        "A.18 warrant should have required_approvers"
    );
    let approvers = warrant.payload.required_approvers.as_ref().unwrap();
    assert_eq!(approvers.len(), 2, "A.18 should have 2 required approvers");
    assert_eq!(
        warrant.payload.min_approvals,
        Some(1),
        "A.18 should require minimum 1 approval"
    );

    // Verify approvers are worker and worker2
    assert!(
        approvers.contains(&worker.public_key()),
        "A.18 approvers should include worker"
    );
    assert!(
        approvers.contains(&worker2.public_key()),
        "A.18 approvers should include worker2"
    );

    // Verify the warrant passes chain verification (the multi-sig is valid config)
    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    let result = data_plane.verify_chain(&[warrant]);
    assert!(
        result.is_ok(),
        "A.18 verify_chain should ACCEPT valid multi-sig warrant: {:?}",
        result.err()
    );
}

// Helper function to sign a payload
fn sign_payload(payload: &payload::WarrantPayload, signing_key: &SigningKey) -> Warrant {
    // Serialize payload to CBOR
    let mut payload_bytes = Vec::new();
    ciborium::ser::into_writer(payload, &mut payload_bytes).expect("Failed to serialize payload");

    // Create preimage: envelope_version || payload_bytes
    // (signing_key.sign() will automatically add "tenuo-warrant-v1" context prefix)
    let mut preimage = Vec::with_capacity(1 + payload_bytes.len());
    preimage.push(1); // envelope_version
    preimage.extend_from_slice(&payload_bytes);

    // Sign (context prefix added automatically by SigningKey::sign)
    let signature = signing_key.sign(&preimage);

    Warrant {
        payload: payload.clone(),
        signature,
        payload_bytes,
        envelope_version: 1,
    }
}

fn sha256(data: &[u8]) -> [u8; 32] {
    use sha2::{Digest, Sha256};
    let mut hasher = Sha256::new();
    hasher.update(data);
    hasher.finalize().into()
}

// ============================================================================
// A.19 CONSTRAINT TYPE COVERAGE
// ============================================================================

/// Test Vector A.19.1: Range Constraint
/// Validates that Range constraints correctly accept/reject numeric values.
#[test]
fn test_vector_a19_1_range_constraint() {
    use std::collections::HashMap;
    use std::time::Duration;

    let control_plane = control_plane_key();
    let worker = worker_key();

    // Build warrant with Range constraint: count must be 0..100
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "count".to_string(),
        Constraint::Range(Range::new(Some(0.0), Some(100.0)).unwrap()),
    );

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("api_call", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .build(&control_plane)
        .expect("Failed to build Range warrant");

    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    // Valid: count = 50 (within range)
    let mut valid_args: HashMap<String, ConstraintValue> = HashMap::new();
    valid_args.insert("count".to_string(), ConstraintValue::Float(50.0));

    let pop = warrant.sign(&worker, "api_call", &valid_args).unwrap();
    let result = data_plane.check_chain(
        std::slice::from_ref(&warrant),
        "api_call",
        &valid_args,
        Some(&pop),
        &[],
    );
    assert!(
        result.is_ok(),
        "A.19.1 Range should ACCEPT value within bounds: {:?}",
        result.err()
    );

    // Invalid: count = 150 (outside range)
    let mut invalid_args: HashMap<String, ConstraintValue> = HashMap::new();
    invalid_args.insert("count".to_string(), ConstraintValue::Float(150.0));

    let pop = warrant.sign(&worker, "api_call", &invalid_args).unwrap();
    let result = data_plane.check_chain(&[warrant], "api_call", &invalid_args, Some(&pop), &[]);
    assert!(
        result.is_err(),
        "A.19.1 Range should REJECT value outside bounds"
    );
}

/// Test Vector A.19.2: OneOf Constraint
/// Validates that OneOf constraints correctly accept/reject string values.
#[test]
fn test_vector_a19_2_oneof_constraint() {
    use std::collections::HashMap;
    use std::time::Duration;

    let control_plane = control_plane_key();
    let worker = worker_key();

    // Build warrant with OneOf constraint: env must be "staging" or "production"
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "env".to_string(),
        Constraint::OneOf(OneOf::new(vec!["staging", "production"])),
    );

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("deploy", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .build(&control_plane)
        .expect("Failed to build OneOf warrant");

    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    // Valid: env = "staging"
    let mut valid_args: HashMap<String, ConstraintValue> = HashMap::new();
    valid_args.insert(
        "env".to_string(),
        ConstraintValue::String("staging".to_string()),
    );

    let pop = warrant.sign(&worker, "deploy", &valid_args).unwrap();
    let result = data_plane.check_chain(
        std::slice::from_ref(&warrant),
        "deploy",
        &valid_args,
        Some(&pop),
        &[],
    );
    assert!(
        result.is_ok(),
        "A.19.2 OneOf should ACCEPT value in set: {:?}",
        result.err()
    );

    // Invalid: env = "development" (not in set)
    let mut invalid_args: HashMap<String, ConstraintValue> = HashMap::new();
    invalid_args.insert(
        "env".to_string(),
        ConstraintValue::String("development".to_string()),
    );

    let pop = warrant.sign(&worker, "deploy", &invalid_args).unwrap();
    let result = data_plane.check_chain(&[warrant], "deploy", &invalid_args, Some(&pop), &[]);
    assert!(
        result.is_err(),
        "A.19.2 OneOf should REJECT value not in set"
    );
}

/// Test Vector A.19.3: CIDR Constraint
/// Validates that CIDR constraints correctly accept/reject IP addresses.
#[test]
fn test_vector_a19_3_cidr_constraint() {
    use std::collections::HashMap;
    use std::time::Duration;

    let control_plane = control_plane_key();
    let worker = worker_key();

    // Build warrant with CIDR constraint: ip must be in 10.0.0.0/8
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "ip".to_string(),
        Constraint::Cidr(Cidr::new("10.0.0.0/8").expect("valid CIDR")),
    );

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("connect", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .build(&control_plane)
        .expect("Failed to build CIDR warrant");

    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    // Valid: ip = "10.1.2.3" (within 10.0.0.0/8)
    let mut valid_args: HashMap<String, ConstraintValue> = HashMap::new();
    valid_args.insert(
        "ip".to_string(),
        ConstraintValue::String("10.1.2.3".to_string()),
    );

    let pop = warrant.sign(&worker, "connect", &valid_args).unwrap();
    let result = data_plane.check_chain(
        std::slice::from_ref(&warrant),
        "connect",
        &valid_args,
        Some(&pop),
        &[],
    );
    assert!(
        result.is_ok(),
        "A.19.3 CIDR should ACCEPT IP in network: {:?}",
        result.err()
    );

    // Invalid: ip = "192.168.1.1" (not in 10.0.0.0/8)
    let mut invalid_args: HashMap<String, ConstraintValue> = HashMap::new();
    invalid_args.insert(
        "ip".to_string(),
        ConstraintValue::String("192.168.1.1".to_string()),
    );

    let pop = warrant.sign(&worker, "connect", &invalid_args).unwrap();
    let result = data_plane.check_chain(&[warrant], "connect", &invalid_args, Some(&pop), &[]);
    assert!(
        result.is_err(),
        "A.19.3 CIDR should REJECT IP outside network"
    );
}

// ============================================================================
// A.20 POP FAILURE CASES
// ============================================================================

/// Test Vector A.20.1: PoP with Wrong Holder Key
/// PoP signed by attacker's key, not the warrant holder's key.
#[test]
fn test_vector_a20_1_pop_wrong_holder_key() {
    use std::collections::HashMap;
    use std::time::Duration;

    let control_plane = control_plane_key();
    let worker = worker_key();
    let attacker = SigningKey::generate(); // Wrong key

    // Build warrant held by worker
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("read_file", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .build(&control_plane)
        .expect("Failed to build warrant");

    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    // Create PoP signed by ATTACKER (wrong key)
    let mut args: HashMap<String, ConstraintValue> = HashMap::new();
    args.insert(
        "path".to_string(),
        ConstraintValue::String("/data/test.txt".to_string()),
    );

    let pop = warrant.sign(&attacker, "read_file", &args).unwrap();

    // Verify with PoP - should fail because signer != holder
    let result = data_plane.check_chain(&[warrant], "read_file", &args, Some(&pop), &[]);
    assert!(
        result.is_err(),
        "A.20.1 should REJECT PoP signed by wrong key"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("signature")
            || err_msg.contains("PoP")
            || err_msg.contains("invalid")
            || err_msg.contains("holder"),
        "A.20.1 error should mention signature/PoP issue: {}",
        err_msg
    );
}

/// Test Vector A.20.2: PoP with Expired Window
/// Tests that PoP window configuration works.
///
/// NOTE: The full expired window test requires time mocking or sleep.
/// This test verifies that window configuration is functional.
#[test]
fn test_vector_a20_2_pop_expired_window() {
    use std::collections::HashMap;
    use std::time::Duration;

    let control_plane = control_plane_key();
    let worker = worker_key();

    // Build warrant
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "path".to_string(),
        Constraint::Pattern(Pattern::new("/data/*").unwrap()),
    );

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("read_file", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .build(&control_plane)
        .expect("Failed to build warrant");

    // Create authorizer with default PoP window (30 seconds, 5 windows)
    let authorizer = Authorizer::builder()
        .trusted_root(control_plane.public_key())
        // Use default pop_window settings via build()
        .build()
        .expect("Failed to build authorizer");

    let mut args: HashMap<String, ConstraintValue> = HashMap::new();
    args.insert(
        "path".to_string(),
        ConstraintValue::String("/data/test.txt".to_string()),
    );

    // Create a valid PoP and verify it works
    let pop = warrant.sign(&worker, "read_file", &args).unwrap();
    let result = authorizer.authorize_one(&warrant, "read_file", &args, Some(&pop), &[]);

    // With default window, fresh PoP should pass
    assert!(
        result.is_ok(),
        "A.20.2 fresh PoP should PASS with default window: {:?}",
        result.err()
    );

    // The PoP window mechanism is verified by the check logic in verify_pop().
    // Full time-based expiry testing would require time mocking.
}

// ============================================================================
// A.21 SIGNED APPROVAL (MULTI-SIG)
// ============================================================================

/// Test Vector A.21.1: Valid Multi-Sig Approval
/// Warrant requiring 2-of-3 approvers with sufficient approvals provided.
#[test]
fn test_vector_a21_1_valid_multisig_approval() {
    use chrono::Utc;
    use std::collections::HashMap;
    use std::time::Duration;
    use tenuo::approval::{compute_request_hash, ApprovalPayload, SignedApproval};
    use tenuo::approval_gate::{encode_approval_gate_map, ApprovalGateMap, ToolApprovalGate};

    let control_plane = control_plane_key();
    let worker = worker_key();
    let approver1 = SigningKey::generate();
    let approver2 = SigningKey::generate();
    let approver3 = SigningKey::generate();

    // Build warrant requiring 2 of 3 approvers
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "amount".to_string(),
        Constraint::Range(Range::new(Some(0.0), Some(10000.0)).unwrap()),
    );

    let mut gates = ApprovalGateMap::new();
    gates.insert("transfer".to_string(), ToolApprovalGate::whole_tool());

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("transfer", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .required_approvers(vec![
            approver1.public_key(),
            approver2.public_key(),
            approver3.public_key(),
        ])
        .min_approvals(2)
        .extension(
            "tenuo.approval_gates",
            encode_approval_gate_map(&gates).unwrap(),
        )
        .build(&control_plane)
        .expect("Failed to build multi-sig warrant");

    let authorizer = Authorizer::new().with_trusted_root(control_plane.public_key());

    let mut args: HashMap<String, ConstraintValue> = HashMap::new();
    args.insert("amount".to_string(), ConstraintValue::Float(500.0));

    // Compute request hash
    let request_hash = compute_request_hash(
        &warrant.id().to_string(),
        "transfer",
        &args,
        Some(&worker.public_key()),
    );

    let now = Utc::now();
    let expires = now + chrono::Duration::hours(1);

    // Create approvals from 2 approvers
    let payload1 = ApprovalPayload {
        version: 1,
        request_hash,
        nonce: rand::random(),
        external_id: "approver1@example.com".to_string(),
        approved_at: now.timestamp() as u64,
        expires_at: expires.timestamp() as u64,
        extensions: None,
    };
    let approval1 = SignedApproval::create(payload1, &approver1);

    let payload2 = ApprovalPayload {
        version: 1,
        request_hash,
        nonce: rand::random(),
        external_id: "approver2@example.com".to_string(),
        approved_at: now.timestamp() as u64,
        expires_at: expires.timestamp() as u64,
        extensions: None,
    };
    let approval2 = SignedApproval::create(payload2, &approver2);

    let pop = warrant.sign(&worker, "transfer", &args).unwrap();
    let result = authorizer.authorize_one(
        &warrant,
        "transfer",
        &args,
        Some(&pop),
        &[approval1, approval2],
    );
    assert!(
        result.is_ok(),
        "A.21.1 should ACCEPT with sufficient approvals: {:?}",
        result.err()
    );
}

/// Test Vector A.21.2: Insufficient Approvals
/// Warrant requiring 2-of-2 but only 1 approval provided.
#[test]
fn test_vector_a21_2_insufficient_approvals() {
    use chrono::Utc;
    use std::collections::HashMap;
    use std::time::Duration;
    use tenuo::approval::{compute_request_hash, ApprovalPayload, SignedApproval};
    use tenuo::approval_gate::{encode_approval_gate_map, ApprovalGateMap, ToolApprovalGate};

    let control_plane = control_plane_key();
    let worker = worker_key();
    let approver1 = SigningKey::generate();
    let approver2 = SigningKey::generate();

    // Build warrant requiring 2 approvers
    let mut constraint_set = ConstraintSet::new();
    constraint_set.insert(
        "amount".to_string(),
        Constraint::Range(Range::new(Some(0.0), Some(10000.0)).unwrap()),
    );

    let mut gates = ApprovalGateMap::new();
    gates.insert("transfer".to_string(), ToolApprovalGate::whole_tool());

    let warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("transfer", constraint_set)
        .ttl(Duration::from_secs(3600))
        .holder(worker.public_key())
        .required_approvers(vec![approver1.public_key(), approver2.public_key()])
        .min_approvals(2)
        .extension(
            "tenuo.approval_gates",
            encode_approval_gate_map(&gates).unwrap(),
        )
        .build(&control_plane)
        .expect("Failed to build multi-sig warrant");

    let authorizer = Authorizer::new().with_trusted_root(control_plane.public_key());

    let mut args: HashMap<String, ConstraintValue> = HashMap::new();
    args.insert("amount".to_string(), ConstraintValue::Float(500.0));

    // Create request hash and only 1 approval
    let request_hash = compute_request_hash(&warrant.id().to_string(), "transfer", &args, None);

    let now = Utc::now();
    let expires = now + chrono::Duration::hours(1);

    let payload = ApprovalPayload {
        version: 1,
        request_hash,
        nonce: rand::random(),
        external_id: "approver1@example.com".to_string(),
        approved_at: now.timestamp() as u64,
        expires_at: expires.timestamp() as u64,
        extensions: None,
    };
    let approval1 = SignedApproval::create(payload, &approver1);

    let pop = warrant.sign(&worker, "transfer", &args).unwrap();
    let result = authorizer.authorize_one(&warrant, "transfer", &args, Some(&pop), &[approval1]);
    assert!(
        result.is_err(),
        "A.21.2 should REJECT with insufficient approvals"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("approval")
            || err_msg.contains("threshold")
            || err_msg.contains("insufficient")
            || err_msg.contains("Insufficient"),
        "A.21.2 error should mention approval issue: {}",
        err_msg
    );
}

// ============================================================================
// A.22 CASCADING REVOCATION
// ============================================================================

/// Test Vector A.22: Cascading Revocation
/// If a middle warrant in a chain is revoked, the entire chain should fail.
#[test]
fn test_vector_a22_cascading_revocation() {
    use std::time::Duration;
    use tenuo::revocation::SignedRevocationList;

    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Build 2-level chain: Root → Worker
    let root_warrant = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("read_file", ConstraintSet::new())
        .max_depth(3)
        .ttl(Duration::from_secs(3600))
        .holder(orchestrator.public_key())
        .build(&control_plane)
        .expect("Failed to build root warrant");

    let worker_warrant = root_warrant
        .attenuate()
        .capability("read_file", ConstraintSet::new())
        .ttl(Duration::from_secs(1800))
        .holder(worker.public_key())
        .build(&orchestrator)
        .expect("Failed to build worker warrant");

    // Create SRL revoking the worker_warrant
    let srl = SignedRevocationList::builder()
        .revoke(worker_warrant.id().to_string())
        .version(1)
        .build(&control_plane)
        .expect("Failed to build SRL");

    // Create authorizer with the SRL loaded
    let authorizer = Authorizer::builder()
        .trusted_root(control_plane.public_key())
        .revocation_list(srl, control_plane.public_key())
        .build()
        .expect("Failed to build authorizer with SRL");

    // Verify chain - should fail because worker warrant is revoked
    let result = authorizer.verify_chain(&[root_warrant, worker_warrant]);
    assert!(
        result.is_err(),
        "A.22 chain with revoked warrant should FAIL"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("revoked") || err_msg.contains("Revoked"),
        "A.22 error should mention revocation: {}",
        err_msg
    );
}

// ============================================================================
// A.23 SESSION MISMATCH
// ============================================================================

/// Test Vector A.23: Session Mismatch (verify_chain_strict)
/// Chain with mismatched session IDs should fail strict verification.
///
/// NOTE: session_id is inherited during attenuation and cannot be changed.
/// We simulate mismatch by mixing warrants from different session contexts.
#[test]
fn test_vector_a23_session_mismatch() {
    use std::time::Duration;

    let control_plane = control_plane_key();
    let orchestrator = orchestrator_key();
    let worker = worker_key();

    // Build root WITH session_id = "sess-abc"
    let root_with_session = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("read_file", ConstraintSet::new())
        .max_depth(3)
        .ttl(Duration::from_secs(3600))
        .holder(orchestrator.public_key())
        .session_id("sess-abc")
        .build(&control_plane)
        .expect("Failed to build root warrant with session");

    // Build root WITHOUT session_id
    let root_no_session = Warrant::builder()
        .r#type(warrant::WarrantType::Execution)
        .capability("read_file", ConstraintSet::new())
        .max_depth(3)
        .ttl(Duration::from_secs(3600))
        .holder(orchestrator.public_key())
        // No session_id
        .build(&control_plane)
        .expect("Failed to build root warrant without session");

    // Child from root_no_session (inherits no session)
    let child_no_session = root_no_session
        .attenuate()
        .inherit_all()
        .holder(worker.public_key())
        .build(&orchestrator)
        .expect("Failed to build child warrant");

    let mut data_plane = DataPlane::new();
    data_plane.trust_issuer("root", control_plane.public_key());

    // Verify chain with mismatched sessions:
    // root_with_session (has session) -> child_no_session (no session)
    // NOTE: This simulates mixing warrants from different session contexts,
    // which verify_chain_strict should reject.
    let result = data_plane.verify_chain_strict(&[root_with_session, child_no_session]);
    assert!(
        result.is_err(),
        "A.23 verify_chain_strict should REJECT mismatched sessions"
    );
    let err_msg = result.unwrap_err().to_string();
    assert!(
        err_msg.contains("session")
            || err_msg.contains("Session")
            || err_msg.contains("mismatch")
            || err_msg.contains("parent"),
        "A.23 error should mention session/chain issue: {}",
        err_msg
    );
}

// =============================================================================
// A.24: SignedApproval Envelope
// =============================================================================

#[test]
fn test_vector_a24_signed_approval_envelope() {
    use chrono::{TimeZone, Utc};
    use sha2::Digest;
    use tenuo::approval::{ApprovalPayload, SignedApproval};

    let approver_keypair = SigningKey::from_bytes(&[0x11; 32]);
    let holder = SigningKey::from_bytes(&[0x03; 32]);

    // Create request hash simulating H(warrant_id || tool || args || holder)
    let mut hasher = sha2::Sha256::new();
    hasher.update(b"tnu_wrt_test_warrant_id");
    hasher.update(b"read_file");
    hasher.update(b"path=/data/sensitive.txt");
    hasher.update(holder.public_key().to_bytes());
    let request_hash: [u8; 32] = hasher.finalize().into();

    // Create approval with proper signature
    let approved_at = Utc.with_ymd_and_hms(2024, 1, 1, 0, 0, 0).unwrap();
    let expires_at = Utc.with_ymd_and_hms(2024, 1, 1, 1, 0, 0).unwrap();

    let payload = ApprovalPayload::new(
        request_hash,
        TEST_VECTOR_NONCE,
        "arn:aws:iam::123456789012:user/security-admin".to_string(),
        approved_at,
        expires_at,
    );

    let signed_approval = SignedApproval::create(payload, &approver_keypair);

    // Verify the approval (note: will only succeed within TTL, so we skip temporal checks in this test)
    // Just verify the envelope is properly constructed
    assert_eq!(
        signed_approval.approver_key.to_bytes(),
        approver_keypair.public_key().to_bytes(),
        "A.24 Approver key should match"
    );

    // The signature should be valid over the payload
    assert_eq!(
        signed_approval.approval_version, 1,
        "A.24 Approval version should be 1"
    );

    // Payload should be non-empty CBOR
    assert!(
        !signed_approval.payload.is_empty(),
        "A.24 Payload should be non-empty"
    );
}

// =============================================================================
// A.25: Additional Constraint Types
// =============================================================================

#[test]
fn test_vector_a25_1_urlsafe_constraint() {
    use tenuo::constraints::UrlSafe;

    let urlsafe = UrlSafe::new();

    // Valid external URLs should pass
    let valid_input = ConstraintValue::String("https://api.example.com/v1/users".to_string());
    assert!(
        urlsafe.matches(&valid_input).unwrap_or(false),
        "A.25.1 UrlSafe should accept valid external URL"
    );

    // AWS metadata URL should fail (SSRF protection)
    let metadata_url =
        ConstraintValue::String("http://169.254.169.254/latest/meta-data/".to_string());
    assert!(
        !urlsafe.matches(&metadata_url).unwrap_or(true),
        "A.25.1 UrlSafe should reject AWS metadata URL"
    );

    // Localhost should fail
    let localhost = ConstraintValue::String("http://localhost:8080/".to_string());
    assert!(
        !urlsafe.matches(&localhost).unwrap_or(true),
        "A.25.1 UrlSafe should reject localhost"
    );
}

#[test]
fn test_vector_a25_2_subpath_constraint() {
    use tenuo::constraints::Subpath;

    let subpath = Subpath::new("/home/agent/workspace").expect("Valid subpath");

    // Valid contained path
    let valid = ConstraintValue::String("/home/agent/workspace/reports/q3.pdf".to_string());
    assert!(
        subpath.matches(&valid).unwrap_or(false),
        "A.25.2 Subpath should accept contained path"
    );

    // Path traversal attack should fail
    let traversal =
        ConstraintValue::String("/home/agent/workspace/../../../etc/passwd".to_string());
    assert!(
        !subpath.matches(&traversal).unwrap_or(true),
        "A.25.2 Subpath should reject traversal attack"
    );

    // Path outside root should fail
    let outside = ConstraintValue::String("/etc/passwd".to_string());
    assert!(
        !subpath.matches(&outside).unwrap_or(true),
        "A.25.2 Subpath should reject path outside root"
    );
}

#[test]
fn test_vector_a25_3_contains_constraint() {
    use tenuo::constraints::Contains;

    let contains = Contains::new(vec!["approved", "reviewed"]);

    // List containing required values should pass
    let valid = ConstraintValue::List(vec![
        ConstraintValue::String("approved".to_string()),
        ConstraintValue::String("reviewed".to_string()),
        ConstraintValue::String("urgent".to_string()),
    ]);
    assert!(
        contains.matches(&valid).unwrap_or(false),
        "A.25.3 Contains should accept list with required values"
    );

    // Missing required value should fail
    let missing = ConstraintValue::List(vec![
        ConstraintValue::String("approved".to_string()),
        ConstraintValue::String("urgent".to_string()),
    ]);
    assert!(
        !contains.matches(&missing).unwrap_or(true),
        "A.25.3 Contains should reject list missing required values"
    );
}

#[test]
fn test_vector_a25_4_subset_constraint() {
    use tenuo::constraints::Subset;

    let subset = Subset::new(vec!["read", "write", "delete"]);

    // Subset should pass
    let valid = ConstraintValue::List(vec![
        ConstraintValue::String("read".to_string()),
        ConstraintValue::String("write".to_string()),
    ]);
    assert!(
        subset.matches(&valid).unwrap_or(false),
        "A.25.4 Subset should accept subset of allowed values"
    );

    // Extra value should fail
    let extra = ConstraintValue::List(vec![
        ConstraintValue::String("read".to_string()),
        ConstraintValue::String("admin".to_string()),
    ]);
    assert!(
        !subset.matches(&extra).unwrap_or(true),
        "A.25.4 Subset should reject list with extra values"
    );
}

#[test]
fn test_vector_a25_5_urlpattern_constraint() {
    use tenuo::constraints::UrlPattern;

    let pattern = UrlPattern::new("https://api.example.com/v1/*").expect("Valid URL pattern");

    // Matching URL should pass
    let valid = ConstraintValue::String("https://api.example.com/v1/users".to_string());
    assert!(
        pattern.matches(&valid).unwrap_or(false),
        "A.25.5 UrlPattern should accept matching URL"
    );

    // Non-matching URL should fail
    let invalid = ConstraintValue::String("https://evil.com/api/v1/users".to_string());
    assert!(
        !pattern.matches(&invalid).unwrap_or(true),
        "A.25.5 UrlPattern should reject non-matching URL"
    );

    // Wrong path should fail
    let wrong_path = ConstraintValue::String("https://api.example.com/v2/users".to_string());
    assert!(
        !pattern.matches(&wrong_path).unwrap_or(true),
        "A.25.5 UrlPattern should reject wrong path"
    );
}
