gaze-pii 0.11.3

use std::collections::hash_map::DefaultHasher;
use std::collections::BTreeSet;
use std::hash::{Hash, Hasher};
use std::ops::Range;
use std::sync::{Arc, OnceLock, RwLock, RwLockReadGuard, RwLockWriteGuard};
use std::time::{Duration, SystemTime, UNIX_EPOCH};

use dashmap::mapref::entry::Entry;
use dashmap::DashMap;
use ed25519_dalek::{Signature, Signer, SigningKey, Verifier, VerifyingKey};
use rand::RngCore;
use regex::Regex;
use secrecy::{ExposeSecret, SecretBox};
use serde::{Deserialize, Deserializer, Serialize};
use serde_json::Value as JsonValue;
use sha2::{Digest, Sha256};

use crate::detector::PiiClass;
use crate::policy::{Policy, SessionScope};
use crate::{Error, Result};
use gaze_types::DocumentExtension;

const DEFAULT_PERSISTENT_TTL_SECS: u64 = 86_400;
const DEFAULT_COUNTER_FAMILY: &str = "counter";
const SNAPSHOT_VERSION_V2: u8 = 2;
const SNAPSHOT_VERSION_V3: u8 = 3;
const SNAPSHOT_VERSION_V4: u8 = 4;
const SNAPSHOT_VERSION_V5: u8 = 5;

pub type RestoreError = Error;

#[derive(Debug, Clone, Copy, PartialEq, Eq)]
#[non_exhaustive]
pub enum RestoreEventKind {
    ManifestBypass,
    FreshPiiDetected,
}

impl RestoreEventKind {
    pub fn as_str(self) -> &'static str {
        match self {
            Self::ManifestBypass => "manifest_bypass",
            Self::FreshPiiDetected => "fresh_pii_detected",
        }
    }
}

#[derive(Debug, Clone, PartialEq, Eq)]
#[non_exhaustive]
pub struct RestoreEvent {
    pub kind: RestoreEventKind,
    pub class: PiiClass,
    pub raw_sha256: String,
    pub location: Range<usize>,
}

#[derive(Debug, Clone, PartialEq, Eq)]
pub(crate) struct ParsedRestoreToken {
    pub class: PiiClass,
    pub ordinal: u32,
    pub raw: String,
}

/// Persistence scope of a [`Session`]'s token manifest.
///
/// `Scope` chooses *persistence*, not *isolation*. A [`Session`] instance is the
/// pseudonym namespace boundary; two Sessions never share counters or value-keyed
/// lookups, regardless of which `Scope` variant they use.
///
/// | Variant | Use case | `export()` allowed |
/// |---------|----------|--------------------|
/// | `Ephemeral` | Process-bound one-off redaction; namespace lives until the Session is dropped | No |
/// | `Conversation(id)` | Keyed multi-turn LLM sessions that can be re-opened across process restarts, storage backend-dependent | Yes |
/// | `Persistent { ttl: Duration }` | Long-lived sessions across restarts | Yes |
///
/// Do not share one `Scope::Ephemeral` Session across logical conversations if
/// each conversation should start with independent `Email_1` / `Person_1`
/// counters. Use one [`Session`] per logical isolation boundary.
///
/// `Persistent`'s `ttl` is a [`std::time::Duration`]. `SensitiveSnapshot`s exported from a
/// persistent session carry the TTL; [`Session::import`] returns `Error::BlobExpired { .. }` once
/// the deadline has elapsed.
#[derive(Debug, Clone)]
#[non_exhaustive]
pub enum Scope {
    Ephemeral,
    Conversation(String),
    Persistent { ttl: Duration },
}

/// Serializable snapshot of a [`Session`]'s token manifest.
///
/// Produced by [`Session::export`] and consumed by [`Session::import`]. Carries the full
/// token-to-PII mapping plus a session signing key - treat it as sensitive as the original
/// document.
///
/// **Storage:** the snapshot is delivered as raw bytes via [`Self::into_bytes`] and reconstructed
/// via `SensitiveSnapshot::from(Vec<u8>)`. There is no `Serialize`/`Deserialize` impl - bytes are
/// the wire format. Encrypt at rest, bind to a conversation/user, enforce a TTL.
///
/// **Must not:** send to the LLM, analytics, browser clients, logs, or support tickets.
///
/// The audit log (`gaze-audit`) is **not** a restore source; only this snapshot can reconstruct
/// original PII values.
#[derive(Debug, Clone)]
pub struct SensitiveSnapshot(Vec<u8>);

impl SensitiveSnapshot {
    pub fn into_bytes(self) -> Vec<u8> {
        self.0
    }
}

impl From<Vec<u8>> for SensitiveSnapshot {
    fn from(value: Vec<u8>) -> Self {
        Self(value)
    }
}

#[derive(Debug, Clone, Hash, PartialEq, Eq, Serialize, Deserialize)]
struct TokenKey {
    family: String,
    class: PiiClass,
    raw: String,
}

#[derive(Debug, Clone, Serialize, Deserialize)]
struct SnapshotEntry {
    class: PiiClass,
    raw: String,
    token: String,
    #[serde(default = "default_counter_family")]
    family: String,
}

#[derive(Debug, Clone, PartialEq, Eq)]
pub struct SessionSnapshotEntry {
    pub class: PiiClass,
    pub raw: String,
    pub token: String,
    pub family: String,
}

#[derive(Debug, Clone, Serialize, Deserialize)]
enum SnapshotScope {
    Ephemeral,
    Conversation(String),
    Persistent { ttl_secs: u64 },
}

#[derive(Debug, Clone, Serialize, Deserialize)]
struct SnapshotPayload {
    scope: SnapshotScope,
    #[serde(deserialize_with = "deserialize_session_hex")]
    session_hex: String,
    entries: Vec<SnapshotEntry>,
    #[serde(default)]
    issued_at: u64,
    #[serde(default)]
    next_by_class: Vec<(PiiClass, usize)>,
    #[serde(default, skip_serializing_if = "Option::is_none")]
    document: Option<DocumentExtension>,
}

#[derive(Debug, Clone)]
pub(crate) struct PrefixCacheHit {
    pub raw_len: usize,
    pub clean_text: String,
    pub manifest: Vec<gaze_types::EmittedTokenSpan>,
}

#[derive(Debug, Clone)]
struct PrefixCacheEntry {
    raw: String,
    clean_text: String,
    manifest: Vec<gaze_types::EmittedTokenSpan>,
}

/// Owns the token manifest for one pseudonym namespace.
///
/// A `Session` holds the bidirectional map between PII values and their pseudonymous tokens.
/// Create one per conversation and thread it through every [`Pipeline::redact`] call.
///
/// A `Session` is the boundary of a pseudonym namespace. Each new `Session`
/// starts with fresh per-class counters (`Person_1`, `Email_1`, etc.) and a
/// fresh `session_hex` prefix. Two Sessions never share `next_by_class`,
/// `token_by_value`, or `value_by_token`, regardless of `Scope` variant.
///
/// The [`Scope`] variant chooses *persistence*, not *isolation*:
///
/// - `Scope::Ephemeral` is process-bound. Its namespace lives until the
///   Session is dropped. Use it for ad-hoc one-off redaction. Do not share one
///   `Ephemeral` Session across logical conversations if those conversations
///   should have independent counters and value-to-token mappings.
/// - `Scope::Conversation(String)` is a keyed namespace that can be re-opened
///   across process restarts when the adopter stores and imports the session
///   snapshot. Use it for per-conversation chat or per-thread agents.
/// - `Scope::Persistent { .. }` is a long-lived namespace with a TTL encoded in
///   exported snapshots.
///
/// Picking the wrong variant does not break single-call redaction correctness,
/// but it can produce cross-call linkability: identical raw values fed into one
/// Session always map to the same pseudonym, so downstream consumers can link
/// mentions across contexts that the adopter intended to keep independent.
///
/// # Restore workflow
///
/// 1. Call [`Pipeline::redact`] - returns a [`gaze_types::CleanDocument`] and updates the session
///    map.
/// 2. Call [`Session::export`] to produce a [`SensitiveSnapshot`].
/// 3. Persist the raw bytes (`snapshot.into_bytes()`) **encrypted at rest** - they contain
///    original PII.
/// 4. Send only the cleaned text to the LLM.
/// 5. After the LLM responds, call [`Session::import`] with `SensitiveSnapshot::from(bytes)`.
/// 6. For each token in the LLM response, call [`Session::restore_strict`] (or
///    [`Session::restore`]).
///
/// There is no `Pipeline::restore_text` method - full-text restore is performed by scanning tokens
/// with [`crate::token_shape::pattern`] and calling `restore_strict` per token.
///
/// Document workflows use the same restore root. Call [`Session::export_with_extension`] only when
/// writing a `gaze-document` bundle that needs signed integrity hashes and codec provenance; plain
/// text adopters should keep using [`Session::export`].
///
/// # Round-trip example
///
/// ```rust
/// use gaze::{
///     token_shape, Action, ClassRule, CleanDocument, DefaultRule, Detection, Detector, PiiClass,
///     Pipeline, RawDocument, Scope, SensitiveSnapshot, Session,
/// };
///
/// struct ExampleEmailDetector;
///
/// impl Detector for ExampleEmailDetector {
///     fn detect(&self, input: &str) -> Vec<Detection> {
///         let email = "alice@example.invalid"; // fixture-cited(crates/gaze/src/session.rs:session::tests::snapshot_round_trip_two_families_same_class_raw_preserved_under_shared_counter)
///         input
///             .find(email)
///             .map(|start| Detection::new(start..start + email.len(), PiiClass::Email, "docs"))
///             .into_iter()
///             .collect()
///     }
/// }
///
/// let pipeline = Pipeline::builder()
///     .detector(ExampleEmailDetector)
///     .rule(ClassRule::new(PiiClass::Email, Action::Tokenize))
///     .rule(DefaultRule::new(Action::Preserve))
///     .build()?;
/// let session = Session::new(Scope::Conversation("conv-1".into()))?;
///
/// let CleanDocument::Text(clean) = pipeline.redact(
///     &session,
///     RawDocument::Text("alice@example.invalid".into()), // fixture-cited(crates/gaze/src/session.rs:session::tests::snapshot_round_trip_two_families_same_class_raw_preserved_under_shared_counter)
/// )? else {
///     panic!("text variant expected");
/// };
///
/// // Export before sending clean text to the LLM. Persist `blob` encrypted at rest.
/// let snapshot = session.export()?;
/// let blob: Vec<u8> = snapshot.into_bytes();
///
/// // Restore on the owner side after the LLM responds.
/// let restored_session = Session::import(SensitiveSnapshot::from(blob))?;
/// let mut restored = String::new();
/// let mut last = 0;
/// for m in token_shape::pattern().find_iter(&clean) {
///     restored.push_str(&clean[last..m.start()]);
///     restored.push_str(&restored_session.restore_strict(m.as_str())?);
///     last = m.end();
/// }
/// restored.push_str(&clean[last..]);
/// assert_eq!(restored, "alice@example.invalid"); // fixture-cited(crates/gaze/src/session.rs:session::tests::snapshot_round_trip_two_families_same_class_raw_preserved_under_shared_counter)
/// # Ok::<(), Box<dyn std::error::Error>>(())
/// ```
///
/// See: `docs/explanation/core/session-contract.md` for the full architecture contract.
///
/// [`Pipeline::redact`]: crate::Pipeline::redact
// intentionally not Debug: contains session signing key and token manifest
pub struct Session {
    scope: Scope,
    session_hex: [u8; 4],
    audit_session_id: String,
    next_by_class: DashMap<PiiClass, usize>,
    token_by_value: DashMap<TokenKey, String>,
    value_by_token: DashMap<String, String>,
    prefix_cache: DashMap<u64, PrefixCacheEntry>,
    restore_regex_cache: RwLock<Option<(usize, Arc<Regex>)>>,
    signing_key: SessionKey,
}

impl Session {
    pub fn new(scope: Scope) -> Result<Self> {
        Ok(Self {
            scope,
            session_hex: random_session_hex(),
            audit_session_id: new_audit_session_id(),
            next_by_class: DashMap::new(),
            token_by_value: DashMap::new(),
            value_by_token: DashMap::new(),
            prefix_cache: DashMap::new(),
            restore_regex_cache: RwLock::new(None),
            signing_key: SessionKey::generate()?,
        })
    }

    pub fn from_policy(policy: &Policy) -> Result<Self> {
        Self::from_policy_with_ttl_override(policy, None)
    }

    pub fn from_policy_with_ttl_override(
        policy: &Policy,
        ttl_secs_override: Option<u64>,
    ) -> Result<Self> {
        let scope = match policy.session.scope {
            SessionScope::Ephemeral => Scope::Ephemeral,
            SessionScope::Conversation => Scope::Conversation("cli".to_string()),
            SessionScope::Persistent => {
                let ttl_secs = ttl_secs_override
                    .or(policy.session.ttl_secs)
                    .unwrap_or(DEFAULT_PERSISTENT_TTL_SECS);
                Scope::Persistent {
                    ttl: Duration::from_secs(ttl_secs),
                }
            }
        };

        Self::new(scope)
    }

    pub fn tokenize(&self, class: &PiiClass, raw: &str) -> Result<String> {
        self.tokenize_with_family(DEFAULT_COUNTER_FAMILY, class, raw)
    }

    pub fn tokenize_with_family(
        &self,
        family: &str,
        class: &PiiClass,
        raw: &str,
    ) -> Result<String> {
        self.intern_mapping(Some(family), class, raw, |index| {
            format!("<{}:{}_{}>", self.session_hex(), class.class_name(), index)
        })
    }

    pub fn format_preserving_fake(&self, class: &PiiClass, raw: &str) -> Result<String> {
        self.intern_mapping(None, class, raw, |index| match class {
            PiiClass::Email => format!("email{index}.{}@gaze-fake.invalid", self.session_hex()),
            PiiClass::Name | PiiClass::Location | PiiClass::Organization => format!(
                "{}:{}_{}",
                self.session_hex(),
                class.class_name().to_ascii_lowercase(),
                index
            ),
            // Lowercasing preserves the dedicated `custom:` sentinel namespace
            // for format-preserving fakes, so restore can detect them too.
            PiiClass::Custom(name) => format!("{}:custom:{name}_{index}", self.session_hex()),
        })
    }

    fn intern_mapping<F>(
        &self,
        family: Option<&str>,
        class: &PiiClass,
        raw: &str,
        build: F,
    ) -> Result<String>
    where
        F: FnOnce(usize) -> String,
    {
        let family_key = family.unwrap_or(DEFAULT_COUNTER_FAMILY);
        let key = TokenKey {
            family: family_key.to_string(),
            class: class.clone(),
            raw: raw.to_string(),
        };
        match self.token_by_value.entry(key) {
            Entry::Occupied(existing) => Ok(existing.get().clone()),
            Entry::Vacant(vacant) => {
                let token = {
                    let mut next = self.next_by_class.entry(class.clone()).or_insert(0);
                    *next += 1;
                    build(*next)
                };

                vacant.insert(token.clone());
                self.value_by_token.insert(token.clone(), raw.to_string());
                Ok(token)
            }
        }
    }

    /// Enumerate every live token string emitted by this session.
    ///
    /// Intended for restore-side callers that need to build an exact-literal
    /// alternation regex over the session map (Pass 1 of the two-pass restore
    /// strategy): replacing token-shaped strings via
    /// a class-shape regex alone is unsafe because it either (a) straddles
    /// word boundaries into adjacent text, or (b) misses lowercase
    /// FormatPreserve shapes like `location_1`. Feeding these exact strings
    /// into `regex::escape` and sorting longest-first avoids both pitfalls.
    ///
    /// Returned order is unspecified — callers that rely on longest-first
    /// matching must sort the returned vector themselves.
    pub fn tokens(&self) -> Vec<String> {
        self.value_by_token
            .iter()
            .map(|entry| entry.key().clone())
            .collect()
    }

    pub(crate) fn restore_regex(&self) -> Result<Option<Arc<Regex>>> {
        let token_count = self.value_by_token.len();
        if token_count == 0 {
            return Ok(None);
        }

        {
            let cache = self.restore_regex_cache_read();
            if let Some((cached_count, cached_regex)) = cache.as_ref() {
                if *cached_count == token_count {
                    return Ok(Some(Arc::clone(cached_regex)));
                }
            }
        }

        let mut tokens = self.tokens();
        if tokens.is_empty() {
            return Ok(None);
        }
        tokens.sort_by(|a, b| b.len().cmp(&a.len()).then_with(|| a.cmp(b)));
        let pattern = tokens
            .iter()
            .map(|token| {
                let escaped = regex::escape(token);
                if token.starts_with('<') && token.ends_with('>') {
                    escaped
                } else {
                    format!(r"\b(?:{escaped})\b")
                }
            })
            .collect::<Vec<_>>()
            .join("|");
        let regex = Arc::new(Regex::new(&pattern).map_err(Error::InvalidRegex)?);
        let cached_count = tokens.len();
        *self.restore_regex_cache_write() = Some((cached_count, Arc::clone(&regex)));
        Ok(Some(regex))
    }

    fn restore_regex_cache_read(&self) -> RwLockReadGuard<'_, Option<(usize, Arc<Regex>)>> {
        self.restore_regex_cache
            .read()
            .unwrap_or_else(|poisoned| poisoned.into_inner())
    }

    fn restore_regex_cache_write(&self) -> RwLockWriteGuard<'_, Option<(usize, Arc<Regex>)>> {
        self.restore_regex_cache
            .write()
            .unwrap_or_else(|poisoned| poisoned.into_inner())
    }

    pub fn contains_token(&self, token: &str) -> bool {
        self.value_by_token.contains_key(token)
    }

    pub fn session_hex(&self) -> String {
        hex::encode(self.session_hex)
    }

    pub fn audit_session_id(&self) -> &str {
        &self.audit_session_id
    }

    pub(crate) fn lookup_prefix_cache(&self, text: &str) -> Option<PrefixCacheHit> {
        self.prefix_cache
            .iter()
            .filter_map(|entry| {
                let cached = entry.value();
                (text.starts_with(&cached.raw) && text.is_char_boundary(cached.raw.len())).then(
                    || PrefixCacheHit {
                        raw_len: cached.raw.len(),
                        clean_text: cached.clean_text.clone(),
                        manifest: cached.manifest.clone(),
                    },
                )
            })
            .max_by_key(|hit| hit.raw_len)
    }

    pub(crate) fn store_prefix_cache(
        &self,
        raw: &str,
        clean_text: &str,
        manifest: &[gaze_types::EmittedTokenSpan],
    ) {
        if raw.is_empty() {
            return;
        }
        if self.prefix_cache.len() >= 64 {
            self.prefix_cache.clear();
        }
        self.prefix_cache.insert(
            prefix_cache_hash(raw),
            PrefixCacheEntry {
                raw: raw.to_string(),
                clean_text: clean_text.to_string(),
                manifest: manifest.to_vec(),
            },
        );
    }

    pub fn snapshot_entries(&self) -> Vec<SessionSnapshotEntry> {
        self.token_by_value
            .iter()
            .map(|entry| SessionSnapshotEntry {
                family: entry.key().family.clone(),
                class: entry.key().class.clone(),
                raw: entry.key().raw.clone(),
                token: entry.value().clone(),
            })
            .collect()
    }

    // Original byte spans are preserved by recognizer normalizers per
    // research-855 §Rulepack > Normalization (axis-2 invariant).
    pub fn restore_strict(&self, token: &str) -> Result<String> {
        self.value_by_token
            .get(token)
            .map(|value| value.value().clone())
            .ok_or_else(|| unknown_token_error(token))
    }

    pub fn restore_strict_text(&self, text: &str) -> std::result::Result<String, RestoreError> {
        let tokens = strict_restore_tokens(text)?;
        for token in &tokens {
            if !self.value_by_token.contains_key(token.parsed.raw.as_str()) {
                return Err(unknown_token_error(token.parsed.raw.as_str()));
            }
        }

        let mut restored = String::with_capacity(text.len());
        let mut cursor = 0usize;
        for token in tokens {
            restored.push_str(&text[cursor..token.start]);
            let raw = self
                .value_by_token
                .get(token.parsed.raw.as_str())
                .expect("validated manifest token must remain present");
            restored.push_str(raw.value());
            cursor = token.end;
        }
        restored.push_str(&text[cursor..]);
        Ok(restored)
    }

    pub fn restore_strict_text_with_events(
        &self,
        text: &str,
    ) -> std::result::Result<(String, Vec<RestoreEvent>), RestoreError> {
        let events = self.restore_boundary_events(text);
        let restored = self.restore_strict_text(text)?;
        Ok((restored, events))
    }

    pub fn restore_boundary_events(&self, text: &str) -> Vec<RestoreEvent> {
        restore_boundary_events(text, &authorized_structural_values(self))
    }

    pub fn restore(&self, token: &str) -> Option<String> {
        self.value_by_token
            .get(token)
            .map(|value| value.value().clone())
    }

    pub fn export(&self) -> Result<SensitiveSnapshot> {
        self.export_payload(None)
    }

    /// Export a document-extended snapshot for `gaze-document` bundle manifests.
    ///
    /// Use this instead of [`Session::export`] when writing a document bundle with
    /// `<base>-agent/` files (`clean.md`, `layout.json`, `report.json`, optional
    /// `preview-redacted.png`) plus owner-only `<base>-owner/manifest.bin`. The supplied
    /// [`DocumentExtension`] is serialized inside the signed snapshot payload, so its hashes and
    /// codec audit rows become the integrity root for the agent-facing files. Text-only adopters
    /// should use [`Session::export`]. Current snapshots emit v5 so older readers fail closed
    /// before restore while the signature binds the emitted envelope bytes.
    ///
    /// ```rust
    /// use gaze::{
    ///     CodecAuditRow, CodecCapabilitySet, DocumentExtension, ExtractionDensityPolicy, Scope,
    ///     Session, TextOrigin,
    /// };
    ///
    /// let session = Session::new(Scope::Conversation("doc-1".to_string()))?;
    /// let mut codec = CodecAuditRow::new(
    ///     "gaze.codec.pdf",
    ///     "0.7.0",
    ///     "application/pdf",
    ///     TextOrigin::Hybrid,
    /// );
    /// codec.advertised = CodecCapabilitySet::new(true, true, true, false);
    /// codec.delivered = CodecCapabilitySet::new(true, true, false, false);
    /// codec.extraction_density_policy = ExtractionDensityPolicy::Required(1.0);
    /// let extension = DocumentExtension::builder(1)
    ///     .clean_md_sha256([1; 32])
    ///     .layout_json_sha256([2; 32])
    ///     .report_json_sha256([3; 32])
    ///     .page_count(4)
    ///     .audit_session_id(session.audit_session_id())
    ///     .codec_audit(vec![codec])
    ///     .build()?;
    ///
    /// let manifest_bin = session.export_with_extension(extension)?.into_bytes();
    /// # assert_eq!(manifest_bin[0], 5);
    /// # Ok::<(), Box<dyn std::error::Error>>(())
    /// ```
    ///
    /// Failure modes match [`Session::export`]: ephemeral sessions return
    /// [`Error::ExportForbidden`], JSON encoding failures return [`Error::SnapshotDecode`], and
    /// empty integrity-binding hashes or audit session ids return
    /// [`Error::EmptyDocumentIntegrity`]. `page_count == 0` is allowed because text-only or
    /// degenerate bundles may have no pages while still binding file hashes. Callers must treat the
    /// returned [`SensitiveSnapshot`] as owner-only because it carries the full token-to-PII restore
    /// map. Bundle layout details live in `docs/explanation/document/document-extension.md`.
    pub fn export_with_extension(&self, extension: DocumentExtension) -> Result<SensitiveSnapshot> {
        if extension.clean_md_sha256 == [0; 32]
            || extension.layout_json_sha256 == [0; 32]
            || extension.report_json_sha256 == [0; 32]
            || extension.audit_session_id.is_empty()
        {
            return Err(Error::EmptyDocumentIntegrity);
        }
        self.export_payload(Some(extension))
    }

    fn export_payload(&self, document: Option<DocumentExtension>) -> Result<SensitiveSnapshot> {
        if matches!(self.scope, Scope::Ephemeral) {
            return Err(Error::ExportForbidden);
        }

        // If the host clock is before the Unix epoch, preserve compatibility by
        // exporting `issued_at = 0` rather than failing snapshot export.
        let issued_at = SystemTime::now()
            .duration_since(UNIX_EPOCH)
            .map(|duration| duration.as_secs())
            .unwrap_or(0);

        let payload = SnapshotPayload {
            scope: snapshot_scope(&self.scope),
            session_hex: self.session_hex(),
            entries: self
                .snapshot_entries()
                .into_iter()
                .map(|entry| SnapshotEntry {
                    family: entry.family,
                    class: entry.class,
                    raw: entry.raw,
                    token: entry.token,
                })
                .collect(),
            next_by_class: self
                .next_by_class
                .iter()
                .map(|entry| (entry.key().clone(), *entry.value()))
                .collect(),
            issued_at,
            document,
        };
        let payload_bytes = serde_json::to_vec(&payload).map_err(Error::SnapshotDecode)?;
        let version = SNAPSHOT_VERSION_V5;
        let signing_key = self.signing_key.signing_key();
        let verifying_key = signing_key.verifying_key();
        let verifying_key_bytes = verifying_key.to_bytes();
        let signing_preimage =
            snapshot_signing_preimage(version, &verifying_key_bytes, &payload_bytes);
        let signature = signing_key.sign(&signing_preimage);

        let mut snapshot = Vec::with_capacity(1 + 32 + 64 + payload_bytes.len());
        snapshot.push(version);
        snapshot.extend_from_slice(&verifying_key_bytes);
        snapshot.extend_from_slice(&signature.to_bytes());
        snapshot.extend_from_slice(&payload_bytes);
        Ok(SensitiveSnapshot(snapshot))
    }

    pub fn import(snapshot: SensitiveSnapshot) -> Result<Self> {
        let bytes = snapshot.0;
        if bytes.len() < 97 {
            return Err(Error::InvalidSnapshotSignature);
        }
        let version = bytes[0];
        if version != SNAPSHOT_VERSION_V2
            && version != SNAPSHOT_VERSION_V3
            && version != SNAPSHOT_VERSION_V4
            && version != SNAPSHOT_VERSION_V5
        {
            return Err(Error::InvalidSnapshotVersion(version));
        }

        let verifying_key = VerifyingKey::from_bytes(
            bytes[1..33]
                .try_into()
                .map_err(|_| Error::InvalidSnapshotSignature)?,
        )
        .map_err(|_| Error::InvalidSnapshotSignature)?;
        let signature = Signature::from_bytes(
            bytes[33..97]
                .try_into()
                .map_err(|_| Error::InvalidSnapshotSignature)?,
        );
        let payload_bytes = &bytes[97..];
        let verify_preimage;
        let signed_bytes = if version >= SNAPSHOT_VERSION_V5 {
            let verifying_key_bytes: [u8; 32] = bytes[1..33]
                .try_into()
                .map_err(|_| Error::InvalidSnapshotSignature)?;
            verify_preimage =
                snapshot_signing_preimage(version, &verifying_key_bytes, payload_bytes);
            verify_preimage.as_slice()
        } else {
            payload_bytes
        };
        verifying_key
            .verify(signed_bytes, &signature)
            .map_err(|_| Error::InvalidSnapshotSignature)?;

        let payload = decode_snapshot_payload(payload_bytes)?;
        validate_entry_prefixes(&payload)?;
        let session_hex = session_hex_bytes(&payload.session_hex)?;
        let scope = scope_from_snapshot(payload.scope);
        let issued_at = payload.issued_at;
        if let Scope::Persistent { ttl } = &scope {
            let ttl_secs = ttl.as_secs();
            if issued_at > 0 {
                let now = SystemTime::now()
                    .duration_since(UNIX_EPOCH)
                    .map(|duration| duration.as_secs())
                    .unwrap_or(0);
                if issued_at > now.saturating_add(60) {
                    return Err(Error::InvalidSnapshotSignature);
                }
                if now.saturating_sub(issued_at) > ttl_secs {
                    return Err(Error::BlobExpired {
                        issued_at,
                        ttl_secs,
                    });
                }
            }
        }

        let session = Self {
            scope,
            session_hex,
            audit_session_id: new_audit_session_id(),
            next_by_class: DashMap::new(),
            token_by_value: DashMap::new(),
            value_by_token: DashMap::new(),
            prefix_cache: DashMap::new(),
            restore_regex_cache: RwLock::new(None),
            signing_key: SessionKey::generate()?,
        };
        for entry in payload.entries {
            session.token_by_value.insert(
                TokenKey {
                    family: entry.family,
                    class: entry.class.clone(),
                    raw: entry.raw.clone(),
                },
                entry.token.clone(),
            );
            session
                .value_by_token
                .insert(entry.token.clone(), entry.raw);
            if let Some(index) = parse_token_index(&entry.token) {
                let mut next = session.next_by_class.entry(entry.class).or_insert(0);
                if *next < index {
                    *next = index;
                }
            }
        }
        // Authoritative counter state from the exporter. Overrides any
        // index we reconstructed from parseable token suffixes above so
        // that format-preserving tokens (e.g. `email1.<session>@gaze-fake.invalid`)
        // also round-trip safely.
        for (class, index) in payload.next_by_class {
            let mut next = session.next_by_class.entry(class).or_insert(0);
            if *next < index {
                *next = index;
            }
        }
        Ok(session)
    }
}

fn default_counter_family() -> String {
    DEFAULT_COUNTER_FAMILY.to_string()
}

fn prefix_cache_hash(raw: &str) -> u64 {
    let mut hasher = DefaultHasher::new();
    raw.hash(&mut hasher);
    hasher.finish()
}

fn new_audit_session_id() -> String {
    let millis = SystemTime::now()
        .duration_since(UNIX_EPOCH)
        .map(|duration| duration.as_millis().min(0xffff_ffff_ffff) as u64)
        .unwrap_or(0);
    let mut bytes = [0_u8; 16];
    rand::thread_rng().fill_bytes(&mut bytes[6..]);
    bytes[0] = (millis >> 40) as u8;
    bytes[1] = (millis >> 32) as u8;
    bytes[2] = (millis >> 24) as u8;
    bytes[3] = (millis >> 16) as u8;
    bytes[4] = (millis >> 8) as u8;
    bytes[5] = millis as u8;
    bytes[6] = (bytes[6] & 0x0f) | 0x70;
    bytes[8] = (bytes[8] & 0x3f) | 0x80;
    format!(
        "{:02x}{:02x}{:02x}{:02x}-{:02x}{:02x}-{:02x}{:02x}-{:02x}{:02x}-{:02x}{:02x}{:02x}{:02x}{:02x}{:02x}",
        bytes[0],
        bytes[1],
        bytes[2],
        bytes[3],
        bytes[4],
        bytes[5],
        bytes[6],
        bytes[7],
        bytes[8],
        bytes[9],
        bytes[10],
        bytes[11],
        bytes[12],
        bytes[13],
        bytes[14],
        bytes[15],
    )
}

struct SessionKey {
    secret: SecretBox<[u8; 32]>,
    protection: MemoryProtection,
}

impl SessionKey {
    fn generate() -> Result<Self> {
        let secret = SecretBox::init_with_mut(|bytes: &mut [u8; 32]| {
            rand::thread_rng().fill_bytes(bytes);
        });
        let protection = MemoryProtection::best_effort(secret.expose_secret().as_ptr(), 32);
        Ok(Self { secret, protection })
    }

    fn signing_key(&self) -> SigningKey {
        SigningKey::from_bytes(self.secret.expose_secret())
    }
}

impl Drop for SessionKey {
    fn drop(&mut self) {
        self.protection.unlock();
    }
}

struct MemoryProtection {
    addr: usize,
    len: usize,
    locked: bool,
}

impl MemoryProtection {
    fn best_effort(ptr: *const u8, len: usize) -> Self {
        let locked = lock_memory(ptr, len);
        advise_dontdump(ptr, len);
        Self {
            addr: ptr as usize,
            len,
            locked,
        }
    }

    fn unlock(&mut self) {
        if self.locked {
            unlock_memory(self.addr as *const u8, self.len);
            self.locked = false;
        }
    }
}

fn lock_memory(ptr: *const u8, len: usize) -> bool {
    #[cfg(unix)]
    unsafe {
        if libc::mlock(ptr.cast(), len) == 0 {
            return true;
        }
        tracing::warn!(
            error = %std::io::Error::last_os_error(),
            "session key mlock failed; continuing with unlocked key material"
        );
    }

    false
}

fn unlock_memory(ptr: *const u8, len: usize) {
    #[cfg(unix)]
    unsafe {
        let _ = libc::munlock(ptr.cast(), len);
    }
}

fn advise_dontdump(_ptr: *const u8, _len: usize) {
    #[cfg(any(target_os = "linux", target_os = "android"))]
    unsafe {
        let ptr = _ptr;
        let len = _len;
        let page_size = libc::sysconf(libc::_SC_PAGESIZE);
        if page_size <= 0 {
            return;
        }
        let page_size = page_size as usize;
        let start = (ptr as usize) & !(page_size - 1);
        let end = (ptr as usize + len).div_ceil(page_size) * page_size;
        let aligned_len = end.saturating_sub(start);
        if aligned_len == 0 {
            return;
        }
        let _ = libc::madvise(start as *mut libc::c_void, aligned_len, libc::MADV_DONTDUMP);
    }
}

fn snapshot_scope(scope: &Scope) -> SnapshotScope {
    match scope {
        Scope::Ephemeral => SnapshotScope::Ephemeral,
        Scope::Conversation(id) => SnapshotScope::Conversation(id.clone()),
        Scope::Persistent { ttl } => SnapshotScope::Persistent {
            ttl_secs: ttl.as_secs(),
        },
    }
}

fn scope_from_snapshot(scope: SnapshotScope) -> Scope {
    match scope {
        SnapshotScope::Ephemeral => Scope::Ephemeral,
        SnapshotScope::Conversation(id) => Scope::Conversation(id),
        SnapshotScope::Persistent { ttl_secs } => Scope::Persistent {
            ttl: Duration::from_secs(ttl_secs),
        },
    }
}

#[derive(Debug, Clone, PartialEq, Eq)]
struct StructuralFinding {
    class: PiiClass,
    raw: String,
    canonical: String,
    location: Range<usize>,
}

fn authorized_structural_values(session: &Session) -> BTreeSet<(PiiClass, String)> {
    let mut authorized = BTreeSet::new();
    for entry in session.snapshot_entries() {
        for finding in structural_findings(&entry.raw) {
            authorized.insert((finding.class, finding.canonical));
        }
    }
    authorized
}

fn restore_boundary_events(
    text: &str,
    authorized: &BTreeSet<(PiiClass, String)>,
) -> Vec<RestoreEvent> {
    structural_findings(text)
        .into_iter()
        .map(|finding| RestoreEvent {
            kind: if authorized.contains(&(finding.class.clone(), finding.canonical)) {
                RestoreEventKind::ManifestBypass
            } else {
                RestoreEventKind::FreshPiiDetected
            },
            class: finding.class,
            raw_sha256: raw_sha256(&finding.raw),
            location: finding.location,
        })
        .collect()
}

fn structural_findings(text: &str) -> Vec<StructuralFinding> {
    let mut findings = Vec::new();
    collect_email_findings(text, &mut findings);
    collect_phone_findings(text, &mut findings);
    collect_iban_findings(text, &mut findings);
    collect_credit_card_findings(text, &mut findings);
    collect_api_key_findings(text, &mut findings);
    findings.sort_by(|left, right| {
        left.location
            .start
            .cmp(&right.location.start)
            .then_with(|| {
                (right.location.end - right.location.start)
                    .cmp(&(left.location.end - left.location.start))
            })
    });
    let mut accepted = Vec::new();
    for finding in findings {
        if accepted.iter().any(|existing: &StructuralFinding| {
            finding.location.start < existing.location.end
                && existing.location.start < finding.location.end
        }) {
            continue;
        }
        accepted.push(finding);
    }
    accepted
}

fn collect_email_findings(text: &str, findings: &mut Vec<StructuralFinding>) {
    for matched in email_pattern().find_iter(text) {
        if !restore_email_boundary_accepts(text, &matched.range()) {
            continue;
        }
        let raw = matched.as_str();
        if !is_basic_restore_email(raw) {
            continue;
        }
        findings.push(StructuralFinding {
            class: PiiClass::Email,
            raw: raw.to_string(),
            canonical: raw.to_ascii_lowercase(),
            location: matched.range(),
        });
    }
}

fn collect_phone_findings(text: &str, findings: &mut Vec<StructuralFinding>) {
    for matched in phone_pattern().find_iter(text) {
        let raw = matched.as_str();
        findings.push(StructuralFinding {
            class: PiiClass::custom("phone"),
            raw: raw.to_string(),
            canonical: ascii_digits(raw),
            location: matched.range(),
        });
    }
}

fn collect_iban_findings(text: &str, findings: &mut Vec<StructuralFinding>) {
    for matched in iban_pattern().find_iter(text) {
        let raw = matched.as_str();
        let canonical = iban_canonicalize(raw);
        if !iban_mod97_check(&canonical) {
            continue;
        }
        findings.push(StructuralFinding {
            class: PiiClass::custom("iban"),
            raw: raw.to_string(),
            canonical,
            location: matched.range(),
        });
    }
}

fn collect_credit_card_findings(text: &str, findings: &mut Vec<StructuralFinding>) {
    for matched in card_pattern().find_iter(text) {
        let raw = matched.as_str();
        let canonical = ascii_digits(raw);
        if !luhn_check(&canonical) {
            continue;
        }
        findings.push(StructuralFinding {
            class: PiiClass::custom("credit_card"),
            raw: raw.to_string(),
            canonical,
            location: matched.range(),
        });
    }
}

fn collect_api_key_findings(text: &str, findings: &mut Vec<StructuralFinding>) {
    for matched in api_key_pattern().find_iter(text) {
        let raw = matched.as_str();
        findings.push(StructuralFinding {
            class: PiiClass::custom("api_key"),
            raw: raw.to_string(),
            canonical: raw.to_string(),
            location: matched.range(),
        });
    }
}

fn email_pattern() -> &'static Regex {
    static PATTERN: OnceLock<Regex> = OnceLock::new();
    PATTERN.get_or_init(|| {
        Regex::new(r"(?i)[a-z0-9_][a-z0-9._%+\-]*@[a-z0-9.\-]+\.[a-z]{2,}")
            .expect("email restore DLP regex compiles")
    })
}

fn phone_pattern() -> &'static Regex {
    static PATTERN: OnceLock<Regex> = OnceLock::new();
    PATTERN.get_or_init(|| {
        Regex::new(
            r"(?x)(?:
                \+?1[\s.-]+555[\s.-]*01\d{2}
                |\+44[\s.-]*7700[\s.-]*900\d{3}
                |\+49[\s.-]*1555[\s.-]*0112233
            )\b",
        )
        .expect("phone restore DLP regex compiles")
    })
}

fn iban_pattern() -> &'static Regex {
    static PATTERN: OnceLock<Regex> = OnceLock::new();
    PATTERN.get_or_init(|| {
        Regex::new(r"\b[A-Z]{2}\d{2}(?: ?[A-Z0-9]{4}){2,7} ?[A-Z0-9]{1,4}\b")
            .expect("IBAN restore DLP regex compiles")
    })
}

fn card_pattern() -> &'static Regex {
    static PATTERN: OnceLock<Regex> = OnceLock::new();
    PATTERN.get_or_init(|| {
        Regex::new(r"\b\d(?:[\s-]?\d){12,18}\b").expect("credit-card restore DLP regex compiles")
    })
}

fn api_key_pattern() -> &'static Regex {
    static PATTERN: OnceLock<Regex> = OnceLock::new();
    PATTERN.get_or_init(|| {
        Regex::new(r"\b(?:sk-test-[A-Za-z0-9]{20,}|gaze_test_[A-Za-z0-9]{16,})\b")
            .expect("API-key restore DLP regex compiles")
    })
}

fn is_basic_restore_email(input: &str) -> bool {
    let Some((local, domain)) = input.split_once('@') else {
        return false;
    };
    !local.is_empty() && domain.contains('.') && !domain.starts_with('.') && !domain.ends_with('.')
}

fn restore_email_boundary_accepts(input: &str, span: &std::ops::Range<usize>) -> bool {
    let previous_ok = input[..span.start]
        .chars()
        .next_back()
        .is_none_or(|ch| !is_ascii_email_continuation(ch));
    let next_ok = input[span.end..]
        .chars()
        .next()
        .is_none_or(|ch| !is_ascii_email_continuation(ch));

    previous_ok && next_ok
}

fn is_ascii_email_continuation(ch: char) -> bool {
    ch.is_ascii_alphanumeric() || ch == '_'
}

fn ascii_digits(input: &str) -> String {
    input.chars().filter(char::is_ascii_digit).collect()
}

fn raw_sha256(input: &str) -> String {
    let digest = Sha256::digest(input.as_bytes());
    hex::encode(digest)
}

fn iban_canonicalize(input: &str) -> String {
    input
        .chars()
        .filter(|ch| !ch.is_ascii_whitespace())
        .flat_map(char::to_uppercase)
        .collect()
}

fn iban_mod97_check(input: &str) -> bool {
    let canonical = iban_canonicalize(input);
    if !(15..=34).contains(&canonical.len()) {
        return false;
    }
    if !canonical.chars().all(|ch| ch.is_ascii_alphanumeric()) {
        return false;
    }

    let mut remainder = 0u32;
    for ch in canonical[4..].chars().chain(canonical[..4].chars()) {
        match ch {
            '0'..='9' => {
                remainder = (remainder * 10 + ch.to_digit(10).expect("digit")) % 97;
            }
            'A'..='Z' => {
                let value = u32::from(ch) - u32::from('A') + 10;
                remainder = (remainder * 10 + value / 10) % 97;
                remainder = (remainder * 10 + value % 10) % 97;
            }
            _ => return false,
        }
    }
    remainder == 1
}

fn luhn_check(input: &str) -> bool {
    let mut digits = Vec::new();
    for byte in input.bytes() {
        if !byte.is_ascii_digit() {
            return false;
        }
        digits.push(byte - b'0');
    }
    if !(13..=19).contains(&digits.len()) {
        return false;
    }

    let sum: u32 = digits
        .iter()
        .rev()
        .enumerate()
        .map(|(index, digit)| {
            let mut value = u32::from(*digit);
            if index % 2 == 1 {
                value *= 2;
                if value > 9 {
                    value -= 9;
                }
            }
            value
        })
        .sum();
    sum.is_multiple_of(10)
}

#[derive(Debug, Clone)]
pub(crate) struct StrictRestoreToken {
    pub start: usize,
    pub end: usize,
    pub parsed: ParsedRestoreToken,
}

pub(crate) fn strict_restore_tokens(text: &str) -> Result<Vec<StrictRestoreToken>> {
    let mut tokens = Vec::new();
    for matched in crate::token_shape::pattern().find_iter(text) {
        tokens.push(StrictRestoreToken {
            start: matched.start(),
            end: matched.end(),
            parsed: parsed_restore_token(matched.as_str()),
        });
    }

    for matched in malformed_restore_token_pattern().find_iter(text) {
        if tokens
            .iter()
            .any(|token| matched.start() < token.end && token.start < matched.end())
        {
            continue;
        }
        return Err(unknown_token_error(matched.as_str()));
    }

    tokens.sort_by_key(|token| token.start);
    Ok(tokens)
}

pub(crate) fn unknown_token_error(raw: &str) -> Error {
    let parsed = parsed_restore_token(raw);
    Error::UnknownToken {
        class: parsed.class,
        ordinal: parsed.ordinal,
        raw: parsed.raw,
    }
}

pub(crate) fn parsed_restore_token(raw: &str) -> ParsedRestoreToken {
    let (class, ordinal) = parse_restore_token_parts(raw)
        .unwrap_or_else(|| (PiiClass::Custom("unknown".to_string()), 0));
    ParsedRestoreToken {
        class,
        ordinal,
        raw: raw.to_string(),
    }
}

fn parse_restore_token_parts(raw: &str) -> Option<(PiiClass, u32)> {
    if let Some(rest) = raw.strip_prefix("email") {
        let (ordinal, tail) = rest.split_once('.')?;
        if tail.ends_with("@gaze-fake.invalid") || tail.ends_with("@example.test") {
            return Some((PiiClass::Email, parse_ascii_ordinal(ordinal)?));
        }
    }

    let mut body = raw.strip_prefix('<').unwrap_or(raw);
    body = body.strip_suffix('>').unwrap_or(body);
    if body.len() > 9 && body.as_bytes().get(8) == Some(&b':') && is_session_hex(&body[..8]) {
        body = &body[9..];
    }

    if let Some(rest) = body.strip_prefix("Custom:") {
        let (name, ordinal) = rest.rsplit_once('_')?;
        return Some((
            PiiClass::Custom(name.to_string()),
            parse_ascii_ordinal(ordinal)?,
        ));
    }
    if let Some(rest) = body.strip_prefix("custom:") {
        let (name, ordinal) = rest.rsplit_once('_')?;
        return Some((
            PiiClass::Custom(name.to_string()),
            parse_ascii_ordinal(ordinal)?,
        ));
    }

    let (class, ordinal) = body.rsplit_once('_')?;
    let ordinal = parse_ascii_ordinal(ordinal)?;
    let class = PiiClass::from_canonical_str(class).unwrap_or_else(|| PiiClass::custom(class));
    Some((class, ordinal))
}

fn parse_ascii_ordinal(raw: &str) -> Option<u32> {
    if raw.is_empty() || !raw.bytes().all(|byte| byte.is_ascii_digit()) {
        return None;
    }
    raw.parse().ok()
}

fn malformed_restore_token_pattern() -> &'static Regex {
    static PATTERN: OnceLock<Regex> = OnceLock::new();
    PATTERN.get_or_init(|| {
        Regex::new(r"<(?:[0-9a-f]{8}:)?(?:Email|Name|Location|Organization|email|name|location|organization|Custom:[a-z0-9_]*|custom:[a-z0-9_]*)_?>")
            .expect("malformed restore token regex must compile")
    })
}

fn random_session_hex() -> [u8; 4] {
    let mut bytes = [0u8; 4];
    rand::thread_rng().fill_bytes(&mut bytes);
    bytes
}

fn deserialize_session_hex<'de, D>(deserializer: D) -> std::result::Result<String, D::Error>
where
    D: Deserializer<'de>,
{
    let value = String::deserialize(deserializer)?;
    if is_session_hex(&value) {
        Ok(value)
    } else {
        Err(serde::de::Error::custom(
            "session_hex must be 8 lowercase hex chars",
        ))
    }
}

fn is_session_hex(value: &str) -> bool {
    value.len() == 8
        && value
            .bytes()
            .all(|byte| byte.is_ascii_digit() || (b'a'..=b'f').contains(&byte))
}

fn session_hex_bytes(value: &str) -> Result<[u8; 4]> {
    if !is_session_hex(value) {
        return Err(Error::InvalidSnapshotPayload);
    }
    let decoded = hex::decode(value).map_err(|_| Error::InvalidSnapshotPayload)?;
    decoded
        .try_into()
        .map_err(|_| Error::InvalidSnapshotPayload)
}

fn decode_snapshot_payload(payload_bytes: &[u8]) -> Result<SnapshotPayload> {
    let value: JsonValue = serde_json::from_slice(payload_bytes).map_err(Error::SnapshotDecode)?;
    let Some(session_hex) = value.get("session_hex").and_then(JsonValue::as_str) else {
        return Err(Error::InvalidSnapshotPayload);
    };
    if !is_session_hex(session_hex) {
        return Err(Error::InvalidSnapshotPayload);
    }
    serde_json::from_value(value).map_err(Error::SnapshotDecode)
}

fn validate_entry_prefixes(payload: &SnapshotPayload) -> Result<()> {
    for entry in &payload.entries {
        if !entry_token_matches_session(&entry.token, &payload.session_hex)
            || !crate::token_shape::starts_with_session_prefix(&entry.token)
        {
            return Err(Error::InvalidSnapshotPayload);
        }
    }
    Ok(())
}

fn entry_token_matches_session(token: &str, session_hex: &str) -> bool {
    token.starts_with(&format!("<{session_hex}:"))
        || token.starts_with(&format!("{session_hex}:"))
        || (token.starts_with("email")
            && token
                .split_once('.')
                .and_then(|(_, rest)| rest.strip_suffix("@gaze-fake.invalid"))
                == Some(session_hex))
}

fn parse_token_index(token: &str) -> Option<usize> {
    if let Some(local) = token
        .strip_prefix("email")
        .and_then(|rest| rest.split_once('.').map(|(index, _)| index))
    {
        return parse_ascii_index(local);
    }
    let suffix = token
        .rsplit_once('_')?
        .1
        .strip_suffix('>')
        .unwrap_or(token.rsplit_once('_')?.1);
    parse_ascii_index(suffix)
}

fn parse_ascii_index(raw: &str) -> Option<usize> {
    if raw.is_empty() || !raw.bytes().all(|byte| byte.is_ascii_digit()) {
        return None;
    }
    raw.parse().ok()
}

fn snapshot_signing_preimage(
    version: u8,
    verifying_key_bytes: &[u8; 32],
    payload_bytes: &[u8],
) -> Vec<u8> {
    let mut preimage = Vec::with_capacity(1 + verifying_key_bytes.len() + payload_bytes.len());
    preimage.push(version);
    preimage.extend_from_slice(verifying_key_bytes);
    preimage.extend_from_slice(payload_bytes);
    preimage
}

#[cfg(test)]
mod tests {
    use super::*;

    fn signed_snapshot_v03(payload: SnapshotPayload) -> SensitiveSnapshot {
        let payload_bytes = serde_json::to_vec(&payload).expect("serialize payload");
        signed_snapshot_bytes(1, &payload_bytes)
    }

    fn signed_snapshot_bytes(version: u8, payload_bytes: &[u8]) -> SensitiveSnapshot {
        let key = SessionKey::generate().expect("session key");
        let signing_key = key.signing_key();
        let signature = signing_key.sign(payload_bytes);
        let verifying_key = signing_key.verifying_key();

        let mut snapshot = Vec::with_capacity(1 + 32 + 64 + payload_bytes.len());
        snapshot.push(version);
        snapshot.extend_from_slice(&verifying_key.to_bytes());
        snapshot.extend_from_slice(&signature.to_bytes());
        snapshot.extend_from_slice(payload_bytes);
        SensitiveSnapshot::from(snapshot)
    }

    fn signed_snapshot_v2(payload: SnapshotPayload) -> SensitiveSnapshot {
        let mut snapshot = signed_snapshot_v03(payload).into_bytes();
        snapshot[0] = SNAPSHOT_VERSION_V2;
        SensitiveSnapshot::from(snapshot)
    }

    fn signed_snapshot(payload: SnapshotPayload) -> SensitiveSnapshot {
        let mut snapshot = signed_snapshot_v03(payload).into_bytes();
        snapshot[0] = SNAPSHOT_VERSION_V3;
        SensitiveSnapshot::from(snapshot)
    }

    fn snapshot_payload_json(snapshot: &SensitiveSnapshot) -> JsonValue {
        serde_json::from_slice(&snapshot.0[97..]).expect("snapshot payload json")
    }

    fn document_extension(session: &Session) -> DocumentExtension {
        DocumentExtension::builder(1)
            .clean_md_sha256([1; 32])
            .layout_json_sha256([2; 32])
            .report_json_sha256([3; 32])
            .page_count(1)
            .audit_session_id(session.audit_session_id())
            .build()
            .expect("document extension")
    }

    fn legacy_v0_4_0_accepts_only_v2(snapshot: &SensitiveSnapshot) -> Result<()> {
        let bytes = &snapshot.0;
        if bytes.len() < 97 {
            return Err(Error::InvalidSnapshotSignature);
        }
        let version = bytes[0];
        if version != SNAPSHOT_VERSION_V2 {
            return Err(Error::InvalidSnapshotVersion(version));
        }
        Ok(())
    }

    #[test]
    fn session_key_produces_valid_signatures() {
        let key = SessionKey::generate().expect("session key");
        let signing_key = key.signing_key();
        let message = b"gaze";
        let signature = signing_key.sign(message);

        assert!(signing_key
            .verifying_key()
            .verify(message, &signature)
            .is_ok());
    }

    #[test]
    fn import_accepts_persistent_snapshot_within_ttl() {
        let now = SystemTime::now()
            .duration_since(UNIX_EPOCH)
            .map(|duration| duration.as_secs())
            .unwrap_or(0);
        let snapshot = signed_snapshot(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 300 },
            session_hex: "a7f3b8e2".to_string(),
            entries: Vec::new(),
            issued_at: now,
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(Session::import(snapshot).is_ok());
    }

    #[test]
    fn import_rejects_v03_envelope_byte() {
        let snapshot = signed_snapshot_v03(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 300 },
            session_hex: "a7f3b8e2".to_string(),
            entries: Vec::new(),
            issued_at: 0,
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(matches!(
            Session::import(snapshot),
            Err(Error::InvalidSnapshotVersion(1))
        ));
    }

    #[test]
    fn import_rejects_invalid_session_hex() {
        let snapshot = signed_snapshot(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 300 },
            session_hex: "A7F3B8E2".to_string(),
            entries: Vec::new(),
            issued_at: 0,
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(matches!(
            Session::import(snapshot),
            Err(Error::InvalidSnapshotPayload)
        ));
    }

    #[test]
    fn import_rejects_manifest_entry_prefix_mismatch() {
        let snapshot = signed_snapshot(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 300 },
            session_hex: "a7f3b8e2".to_string(),
            entries: vec![SnapshotEntry {
                family: DEFAULT_COUNTER_FAMILY.to_string(),
                class: PiiClass::Name,
                raw: "Dr. Schmidt".to_string(),
                token: "deadbeef:name_1".to_string(),
            }],
            issued_at: 0,
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(matches!(
            Session::import(snapshot),
            Err(Error::InvalidSnapshotPayload)
        ));
    }

    #[test]
    fn import_rejects_expired_persistent_snapshot() {
        let now = SystemTime::now()
            .duration_since(UNIX_EPOCH)
            .map(|duration| duration.as_secs())
            .unwrap_or(0);
        let snapshot = signed_snapshot(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 10 },
            session_hex: "a7f3b8e2".to_string(),
            entries: Vec::new(),
            issued_at: now.saturating_sub(11),
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(matches!(
            Session::import(snapshot),
            Err(Error::BlobExpired {
                issued_at,
                ttl_secs: 10,
            }) if issued_at == now.saturating_sub(11)
        ));
    }

    #[test]
    fn import_accepts_legacy_persistent_snapshot_without_issued_at() {
        let snapshot = signed_snapshot_v2(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 1 },
            session_hex: "a7f3b8e2".to_string(),
            entries: Vec::new(),
            issued_at: 0,
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(Session::import(snapshot).is_ok());
    }

    #[test]
    fn import_v0_4_0_snapshot_version_2_succeeds_with_default_family() {
        let payload = serde_json::json!({
            "scope": { "Persistent": { "ttl_secs": 300 } },
            "session_hex": "a7f3b8e2",
            "entries": [{
                "class": "Name",
                "raw": "Dr. Schmidt",
                "token": "<a7f3b8e2:Name_1>"
            }],
            "issued_at": 0,
            "next_by_class": [["Name", 1]]
        });
        let payload_bytes = serde_json::to_vec(&payload).expect("payload");
        let snapshot = signed_snapshot_bytes(SNAPSHOT_VERSION_V2, &payload_bytes);

        let session = Session::import(snapshot).expect("import v2 snapshot");
        assert_eq!(
            session.restore("<a7f3b8e2:Name_1>").as_deref(),
            Some("Dr. Schmidt")
        );
        let next = session
            .tokenize_with_family("alpha", &PiiClass::Name, "Prof. Weber")
            .expect("next token");
        assert_eq!(next, "<a7f3b8e2:Name_2>");
    }

    #[test]
    fn v0_4_0_rejects_v0_4_1_snapshot_version_3_cleanly() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let _ = session
            .tokenize_with_family("alpha", &PiiClass::Name, "Dr. Schmidt")
            .expect("token");
        let snapshot = session.export().expect("snapshot");

        assert!(matches!(
            legacy_v0_4_0_accepts_only_v2(&snapshot),
            Err(Error::InvalidSnapshotVersion(SNAPSHOT_VERSION_V5))
        ));
    }

    #[test]
    fn snapshot_signature_binds_emitted_envelope_version() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        session
            .tokenize(&PiiClass::Name, "Dr. Schmidt")
            .expect("token");

        let mut bytes = session.export().expect("snapshot").into_bytes();
        assert_eq!(bytes[0], SNAPSHOT_VERSION_V5);
        bytes[0] = SNAPSHOT_VERSION_V3;

        assert!(matches!(
            Session::import(SensitiveSnapshot::from(bytes)),
            Err(Error::InvalidSnapshotSignature)
        ));
    }

    #[test]
    fn snapshot_signature_uses_final_envelope_preimage() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        session
            .tokenize(&PiiClass::Email, "alice@example.invalid")
            .expect("token");

        let bytes = session.export().expect("snapshot").into_bytes();
        let version = bytes[0];
        let verifying_key_bytes: [u8; 32] = bytes[1..33].try_into().expect("verifying key bytes");
        let verifying_key = VerifyingKey::from_bytes(&verifying_key_bytes).expect("verifying key");
        let signature = Signature::from_bytes(&bytes[33..97].try_into().expect("signature bytes"));
        let payload_bytes = &bytes[97..];
        let preimage = snapshot_signing_preimage(version, &verifying_key_bytes, payload_bytes);

        assert!(verifying_key.verify(&preimage, &signature).is_ok());
        assert!(verifying_key.verify(payload_bytes, &signature).is_err());
    }

    #[test]
    fn snapshot_import_rejects_signature_slot_mutation() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        session
            .tokenize(&PiiClass::Name, "Dr. Schmidt")
            .expect("token");

        let mut bytes = session.export().expect("snapshot").into_bytes();
        bytes[33] ^= 0x01;

        assert!(matches!(
            Session::import(SensitiveSnapshot::from(bytes)),
            Err(Error::InvalidSnapshotSignature)
        ));
    }

    #[test]
    fn export_with_extension_round_trips_clean() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let token = session
            .tokenize(&PiiClass::Name, "Dr. Schmidt")
            .expect("token");
        let extension = document_extension(&session);

        let snapshot = session
            .export_with_extension(extension.clone())
            .expect("export with extension");
        let payload = snapshot_payload_json(&snapshot);

        let document: DocumentExtension =
            serde_json::from_value(payload["document"].clone()).expect("document extension");
        assert_eq!(document, extension);

        let imported = Session::import(snapshot).expect("import extended snapshot");
        assert_eq!(imported.restore(&token).as_deref(), Some("Dr. Schmidt"));
    }

    #[test]
    fn export_with_extension_no_pii_leak() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let _ = session
            .tokenize(&PiiClass::Email, "alice@example.invalid")
            .expect("token");

        let snapshot = session
            .export_with_extension(document_extension(&session))
            .expect("export with extension");
        let payload = snapshot_payload_json(&snapshot);
        let document_json = serde_json::to_string(&payload["document"]).expect("document json");

        assert!(!document_json.contains("alice@example.invalid"));
        assert!(!document_json.contains("\"raw\""));
    }

    #[test]
    fn document_extension_zero_clean_md_sha256_rejected() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let mut extension = document_extension(&session);
        extension.clean_md_sha256 = [0; 32];

        assert!(matches!(
            session.export_with_extension(extension),
            Err(Error::EmptyDocumentIntegrity)
        ));
    }

    #[test]
    fn document_extension_zero_layout_json_sha256_rejected() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let mut extension = document_extension(&session);
        extension.layout_json_sha256 = [0; 32];

        assert!(matches!(
            session.export_with_extension(extension),
            Err(Error::EmptyDocumentIntegrity)
        ));
    }

    #[test]
    fn document_extension_zero_report_json_sha256_rejected() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let mut extension = document_extension(&session);
        extension.report_json_sha256 = [0; 32];

        assert!(matches!(
            session.export_with_extension(extension),
            Err(Error::EmptyDocumentIntegrity)
        ));
    }

    #[test]
    fn document_extension_empty_audit_session_id_rejected() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let mut extension = document_extension(&session);
        extension.audit_session_id.clear();

        assert!(matches!(
            session.export_with_extension(extension),
            Err(Error::EmptyDocumentIntegrity)
        ));
    }

    #[test]
    fn document_extension_with_full_integrity_signs_successfully() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let snapshot = session
            .export_with_extension(document_extension(&session))
            .expect("export with full integrity");
        let payload = snapshot_payload_json(&snapshot);

        assert_eq!(payload["document"]["schema_version"], 1);
        assert!(Session::import(snapshot).is_ok());
    }

    #[test]
    fn import_rejects_forward_dated_persistent_snapshot() {
        let now = SystemTime::now()
            .duration_since(UNIX_EPOCH)
            .map(|duration| duration.as_secs())
            .unwrap_or(0);
        let snapshot = signed_snapshot(SnapshotPayload {
            scope: SnapshotScope::Persistent { ttl_secs: 300 },
            session_hex: "a7f3b8e2".to_string(),
            entries: Vec::new(),
            issued_at: now.saturating_add(3_600),
            next_by_class: Vec::new(),
            document: None,
        });

        assert!(matches!(
            Session::import(snapshot),
            Err(Error::InvalidSnapshotSignature)
        ));
    }

    #[test]
    fn tokenize_distinguishes_builtin_and_custom_class_names() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        for (builtin, name) in [
            (PiiClass::Email, "email"),
            (PiiClass::Name, "name"),
            (PiiClass::Location, "location"),
            (PiiClass::Organization, "organization"),
        ] {
            let builtin_value = format!("{name}-builtin");
            let custom_value = format!("{name}-custom");

            let builtin_token = session
                .tokenize(&builtin, &builtin_value)
                .expect("builtin token");
            let custom_class = PiiClass::custom(name);
            let custom_token = session
                .tokenize(&custom_class, &custom_value)
                .expect("custom token");

            assert!(builtin_token.ends_with(&format!(":{}_1>", builtin.class_name())));
            assert!(custom_token.ends_with(&format!(":Custom:{name}_1>")));
            assert_ne!(builtin_token, custom_token);
            assert_eq!(
                session.restore(&builtin_token).as_deref(),
                Some(builtin_value.as_str())
            );
            assert_eq!(
                session.restore(&custom_token).as_deref(),
                Some(custom_value.as_str())
            );
        }
    }

    #[test]
    fn tokenize_distinguishes_custom_classes_with_matching_pascal_case() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        let first_class = PiiClass::custom("email");
        let second_class = PiiClass::custom("custom_email");

        let first_token = session
            .tokenize(&first_class, "alice@corp.com")
            .expect("first custom token");
        let second_token = session
            .tokenize(&second_class, "hello")
            .expect("second custom token");

        assert!(first_token.ends_with(":Custom:email_1>"));
        assert!(second_token.ends_with(":Custom:custom_email_1>"));
        assert_ne!(first_token, second_token);
        assert_eq!(
            session.restore(&first_token).as_deref(),
            Some("alice@corp.com")
        );
        assert_eq!(session.restore(&second_token).as_deref(), Some("hello"));
    }

    #[test]
    fn snapshot_round_trip_two_families_same_class_raw_preserved_under_shared_counter() {
        let session = Session::new(Scope::Conversation("test".to_string())).expect("session");
        let alpha = session
            .tokenize_with_family("alpha", &PiiClass::Name, "Dr. Schmidt")
            .expect("alpha token");
        let beta = session
            .tokenize_with_family("beta", &PiiClass::Name, "Dr. Schmidt")
            .expect("beta token");

        assert_ne!(alpha, beta);
        assert!(alpha.ends_with(":Name_1>"));
        assert!(beta.ends_with(":Name_2>"));

        let snapshot = session.export().expect("snapshot");
        assert_eq!(snapshot.0[0], SNAPSHOT_VERSION_V5);
        let imported = Session::import(snapshot).expect("import");

        assert_eq!(imported.restore(&alpha).as_deref(), Some("Dr. Schmidt"));
        assert_eq!(imported.restore(&beta).as_deref(), Some("Dr. Schmidt"));
        assert_eq!(
            imported
                .tokenize_with_family("alpha", &PiiClass::Name, "Dr. Schmidt")
                .expect("alpha stable"),
            alpha
        );
        assert_eq!(
            imported
                .tokenize_with_family("beta", &PiiClass::Name, "Dr. Schmidt")
                .expect("beta stable"),
            beta
        );
    }

    #[test]
    fn restore_strict_text_rejects_unknown_token() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        let err = session
            .restore_strict_text("Reply to <deadbeef:Email_999>.")
            .expect_err("unknown token must fail closed");

        assert!(matches!(
            err,
            Error::UnknownToken {
                class: PiiClass::Email,
                ordinal: 999,
                raw,
            } if raw == "<deadbeef:Email_999>"
        ));
    }

    #[test]
    fn restore_strict_text_rejects_malformed_token() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        let err = session
            .restore_strict_text("Reply to <Email_>.")
            .expect_err("malformed token must fail closed");

        assert!(matches!(
            err,
            Error::UnknownToken {
                class: PiiClass::Custom(name),
                ordinal: 0,
                raw,
            } if name == "unknown" && raw == "<Email_>"
        ));
    }

    #[test]
    fn restore_strict_text_rejects_cross_session_token_as_unknown() {
        let source = Session::new(Scope::Ephemeral).expect("source session");
        let token = source
            .tokenize(&PiiClass::Email, "alice@example.invalid")
            .expect("token");
        let target = Session::new(Scope::Ephemeral).expect("target session");

        let err = target
            .restore_strict_text(&format!("Reply to {token}."))
            .expect_err("wrong-session token must fail closed");

        assert!(matches!(
            err,
            Error::UnknownToken {
                class: PiiClass::Email,
                ordinal: 1,
                raw,
            } if raw == token
        ));
    }

    #[test]
    fn restore_strict_text_is_atomic_on_failure() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        let token = session
            .tokenize(&PiiClass::Name, "Dr. Schmidt")
            .expect("token");

        let err = session
            .restore_strict_text(&format!("{token} then <deadbeef:Email_9>"))
            .expect_err("unknown token must prevent partial restore output");

        assert!(matches!(
            err,
            Error::UnknownToken {
                class: PiiClass::Email,
                ordinal: 9,
                raw,
            } if raw == "<deadbeef:Email_9>"
        ));
    }

    #[test]
    fn restore_strict_text_preserves_path_adjacency_byte_exact() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        let workspace = session
            .tokenize(&PiiClass::Organization, "Workspace")
            .expect("workspace token");
        let artist = session
            .tokenize(&PiiClass::Organization, "Artist")
            .expect("artist token");
        let email = session
            .tokenize(&PiiClass::Email, "alice@example.invalid")
            .expect("email token");
        let cases = [
            (
                format!("list all folders in ~/{workspace}"),
                "list all folders in ~/Workspace".to_string(),
            ),
            (format!("{workspace}*"), "Workspace*".to_string()),
            (
                format!("~/{workspace}/{artist}"),
                "~/Workspace/Artist".to_string(),
            ),
            (
                format!("owner={email};path=~/{workspace}"),
                "owner=alice@example.invalid;path=~/Workspace".to_string(),
            ),
        ];

        for (clean, expected) in cases {
            let restored = session
                .restore_strict_text(&clean)
                .expect("restore must succeed");

            assert_eq!(restored, expected);
            assert!(!restored.contains("~/ Workspace"));
        }
    }

    #[test]
    fn restore_boundary_events_distinguish_manifest_bypass_from_fresh_pii() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        let token = session
            .tokenize(&PiiClass::Email, "alice@example.invalid")
            .expect("token");

        let (restored, events) = session
            .restore_strict_text_with_events(&format!(
                "{token} raw alice@example.invalid fresh bob@example.invalid"
            ))
            .expect("restore continues in audit-only mode");

        assert!(restored.contains("alice@example.invalid"));
        assert_eq!(events.len(), 2);
        assert_eq!(events[0].kind, RestoreEventKind::ManifestBypass);
        assert_eq!(events[0].class, PiiClass::Email);
        assert_eq!(events[0].raw_sha256.len(), 64);
        assert_ne!(events[0].raw_sha256, "alice@example.invalid");
        assert_eq!(events[1].kind, RestoreEventKind::FreshPiiDetected);
        assert_eq!(events[1].class, PiiClass::Email);
    }

    #[test]
    fn restore_dlp_email_boundary_accepts_non_ascii_and_punctuation_delimiters() {
        for (input, location) in [
            ("a@example.invalidø", 0..17),
            ("a@example.invalid. Thanks", 0..17),
            ("a@example.invalid-", 0..17),
            ("a@example.invalid+", 0..17),
            ("a@example.invalid%", 0..17),
            (".a@example.invalid", 1..18),
        ] {
            let findings = structural_findings(input);
            let finding = findings
                .iter()
                .find(|finding| finding.class == PiiClass::Email)
                .unwrap_or_else(|| panic!("missing email finding for {input}"));

            assert_eq!(finding.raw, "a@example.invalid", "{input}");
            assert_eq!(finding.location, location, "{input}");
        }

        let adjacent = structural_findings("a@example.invalid,b@example.invalid")
            .into_iter()
            .filter(|finding| finding.class == PiiClass::Email)
            .map(|finding| (finding.raw, finding.location))
            .collect::<Vec<_>>();
        assert_eq!(
            adjacent,
            vec![
                ("a@example.invalid".to_string(), 0..17),
                ("b@example.invalid".to_string(), 18..35)
            ]
        );

        for input in ["a@example.invalid1", "a@example.invalid_"] {
            assert!(
                structural_findings(input)
                    .iter()
                    .all(|finding| finding.class != PiiClass::Email),
                "{input}"
            );
        }
    }

    #[test]
    fn restore_boundary_events_cover_structural_identifier_scope() {
        let session = Session::new(Scope::Ephemeral).expect("session");
        session
            .tokenize(&PiiClass::custom("phone"), "+1-555-0101")
            .expect("phone token");
        session
            .tokenize(&PiiClass::custom("iban"), "DE89 3704 0044 0532 0130 00")
            .expect("iban token");
        session
            .tokenize(&PiiClass::custom("credit_card"), "4111 1111 1111 1111")
            .expect("card token");
        session
            .tokenize(&PiiClass::custom("api_key"), "sk-test-00000000000000000000")
            .expect("api key token");

        let events = session.restore_boundary_events(
            "known +1-555-0101 UK +44 7700 900123 DE +49 1555 0112233 \
             known DE89370400440532013000 fresh GB82 WEST 1234 5698 7654 32 \
             known 4111111111111111 fresh 4012-8888-8888-1881 \
             known sk-test-00000000000000000000 fresh gaze_test_0000000000000000",
        );

        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::ManifestBypass
                && event.class == PiiClass::custom("phone")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::FreshPiiDetected
                && event.class == PiiClass::custom("phone")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::ManifestBypass
                && event.class == PiiClass::custom("iban")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::FreshPiiDetected
                && event.class == PiiClass::custom("iban")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::ManifestBypass
                && event.class == PiiClass::custom("credit_card")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::FreshPiiDetected
                && event.class == PiiClass::custom("credit_card")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::ManifestBypass
                && event.class == PiiClass::custom("api_key")
        }));
        assert!(events.iter().any(|event| {
            event.kind == RestoreEventKind::FreshPiiDetected
                && event.class == PiiClass::custom("api_key")
        }));
    }
}