car-sync 0.50.0

//! End-to-end payload encryption boundary (slice B6 of
//! `docs/proposals/multi-device-sync.md`, §"Transport: Parslee-hosted relay,
//! E2E for personal scope").
//!
//! The proposal's trust posture: **the relay is a dumb, untrusted ordered-log
//! store.** Personal-scope payloads are encrypted end-to-end, always; the
//! relay stores only ciphertext and "can route and dedup on `op_id` and `hlc`
//! (which stay cleartext) but **cannot read conversations, memory, or
//! secrets**." This module is the encrypt/decrypt boundary that realizes it.
//!
//! ## The design that keeps the shipped oplog intact
//!
//! An op's `op_id` is the SHA-256 content address over `device_id ‖ seq ‖ prev
//! ‖ hlc ‖ scope ‖ surface ‖ canonical(payload)` (see [`crate::oplog`]). To
//! keep `op_id`/`seq`/`prev`/`hlc`/`scope`/`surface` **cleartext metadata** —
//! exactly what B3's relay chain-verification and dedup rely on — the
//! encryption is applied to the **payload only, at authoring time**: a device
//! that wants E2E authors its op with `cipher.encrypt(plaintext)` as the
//! payload, so the canonical op the whole system carries is ciphertext-native.
//! The chain hashes over ciphertext, [`crate::oplog::verify_log`] verifies it,
//! and the relay sees only the [`Envelope`]. A peer holding the same key
//! recovers the plaintext with [`PayloadCipher::decrypt`]. No change to the
//! `OpRecord` shape, the journal, the relay, or the fold — the ciphertext is
//! just a `serde_json::Value` like any other payload.
//!
//! ## Real crypto, not a placeholder
//!
//! [`LocalKeyCipher`] is a genuine AEAD: **ChaCha20-Poly1305** with a random
//! 96-bit nonce per op (RustCrypto `chacha20poly1305`). Confidentiality AND
//! integrity — a tampered ciphertext fails the Poly1305 tag and
//! [`PayloadCipher::decrypt`] returns [`CryptoError::Decrypt`], never silently
//! wrong plaintext. The key is a user-held 256-bit secret
//! ([`LocalKeyCipher::load_or_generate`] persists it `0600` under
//! `~/.car/sync/`), never transmitted — the proposal's "the key is user-held,
//! derived at Parslee login, never transmitted."
//!
//! ## What's wired, what remains
//!
//! Shipped + tested here and in the session:
//!
//! - **Decrypt-before-fold** — [`crate::session::SyncSession::with_key_provider`]
//!   encrypts each payload at `append` (ciphertext-native, `op_id` over
//!   ciphertext) and decrypts at `state()` *after* the chain verifies and
//!   *before* the fold groups on `payload["id"]`/`fold_key`. Op identity stays
//!   the cleartext-metadata `op_id`.
//! - **Login-derived key distribution** — [`DerivedKeyProvider`] HKDF-derives
//!   per-audience keys from one master; [`DerivedKeyProvider::from_passphrase`]
//!   is the zero-knowledge cross-device source (same passphrase → same keys on
//!   every device, never transmitted). [`LocalKeyCipher`] remains the raw
//!   single-key reference. Per-audience isolation via [`encryption_audience`].
//! - **Checkpoints under E2E** — [`crate::session::SyncSession::publish_checkpoint`]
//!   is guarded off under a key provider: a ciphertext-folded checkpoint would
//!   form an inconsistent decrypt base, and a cleartext one would leak. The
//!   encrypted op log is retained and cold bootstrap replays it.
//!
//! - **Client-side org-key agreement (authenticated)** — [`wrap_org_key`] /
//!   [`unwrap_org_key`] (ECIES over X25519, [`derive_x25519_identity`]) share ONE
//!   org master key `K_org` across all members so org-scoped ops are mutually
//!   readable, while the relay/platform never sees `K_org`. Each wrap is SIGNED by
//!   the publisher's Ed25519 identity ([`derive_ed25519_identity`]) and unwrap
//!   REFUSES any wrap not signed by a caller-trusted holder — closing the
//!   key-substitution hole. The directory ([`crate::org_key_directory`]),
//!   transport, and the consuming [`crate::org_key_provider::OrgAwareKeyProvider`]
//!   are built on top. It all stays inert; the `login_secret → identity` entropy
//!   dependency MUST be reviewed by a cryptographer before production (see the
//!   security notes above the identity functions).
//!
//! Remaining before activation: **per-scope encrypted checkpoint push** — a
//! whole-chain checkpoint mixes `Personal` + `Shared{org}` audiences, so it must
//! be split per scope key before it can be pushed to an untrusted relay to
//! restore relay-side GC; the oplog **epoch field** + fold key-selection (so old
//! epochs decrypt after **rotation**); the out-of-band `org → K_org` **resolver**
//! that wires `OrgAwareKeyProvider` into the subsystem; and the cryptographer
//! audit itself.

use crate::oplog::{canonical_json, Scope};
use serde::{Deserialize, Serialize};
use serde_json::Value;
use std::path::Path;

use chacha20poly1305::aead::{Aead, AeadCore, KeyInit, OsRng, Payload};
use chacha20poly1305::{ChaCha20Poly1305, Key, Nonce};
use ed25519_dalek::{Signature, Signer, SigningKey, VerifyingKey};
use sha2::Digest;
use x25519_dalek::{PublicKey, StaticSecret};
use zeroize::{Zeroize, Zeroizing};

/// The frozen algorithm tag written into every [`Envelope`] — lets a future
/// cipher upgrade coexist (a decryptor rejects an unknown tag rather than
/// mis-decoding).
pub const ALG_CHACHA20POLY1305: &str = "chacha20poly1305";

/// The ciphertext form of a payload — what the relay stores and sees. Cleartext
/// `op_id`/`seq`/`hlc`/`scope`/`surface` metadata lives *outside* this, on the
/// [`crate::oplog::OpRecord`]; the envelope hides only the payload body.
#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct Envelope {
    /// Algorithm tag ([`ALG_CHACHA20POLY1305`]).
    pub car_enc: String,
    /// The 96-bit AEAD nonce, hex (24 chars). Random per encryption, so the
    /// same plaintext encrypts to distinct ciphertext each time.
    pub nonce: String,
    /// The ciphertext ‖ Poly1305 tag, hex.
    pub ct: String,
    /// Org key-id (rotation EPOCH). ONLY the multi-epoch org cipher sets it, so a
    /// remaining member can select the right per-epoch key after a rotation instead
    /// of trial-decrypting. Personal / wrap envelopes omit it.
    ///
    /// `skip_serializing_if` is LOAD-BEARING: personal envelopes stay byte-identical
    /// (the field never serializes), AND `wrap_org_key` signs `canonical_json(envelope)`
    /// — so an always-omitted `kid` keeps every Ed25519 wrap signature valid. Do NOT
    /// drop `skip_serializing_if`, and do NOT add `deny_unknown_fields`.
    #[serde(default, skip_serializing_if = "Option::is_none")]
    pub kid: Option<u64>,
}

impl Envelope {
    /// Is this JSON value a ciphertext envelope (vs. a cleartext payload)?
    pub fn is_envelope(v: &Value) -> bool {
        v.get("car_enc").and_then(Value::as_str) == Some(ALG_CHACHA20POLY1305)
            && v.get("nonce").is_some()
            && v.get("ct").is_some()
    }
}

/// A crypto-boundary failure.
#[derive(Debug)]
pub enum CryptoError {
    /// Serializing the plaintext payload / deserializing the recovered plaintext.
    Json(serde_json::Error),
    /// The envelope is malformed, or its algorithm tag is unknown.
    BadEnvelope(String),
    /// AEAD open failed — a wrong key OR a tampered ciphertext/nonce (Poly1305
    /// tag mismatch). Indistinguishable by design; both mean "do not trust".
    Decrypt,
    /// The persisted key file is the wrong length or unreadable.
    Key(String),
    /// I/O reading/writing the key file.
    Io(std::io::Error),
}

impl std::fmt::Display for CryptoError {
    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
        match self {
            CryptoError::Json(e) => write!(f, "crypto payload json error: {e}"),
            CryptoError::BadEnvelope(d) => write!(f, "crypto envelope malformed: {d}"),
            CryptoError::Decrypt => {
                write!(
                    f,
                    "crypto decrypt failed (wrong key or tampered ciphertext)"
                )
            }
            CryptoError::Key(d) => write!(f, "crypto key error: {d}"),
            CryptoError::Io(e) => write!(f, "crypto io error: {e}"),
        }
    }
}

impl std::error::Error for CryptoError {}

impl From<serde_json::Error> for CryptoError {
    fn from(e: serde_json::Error) -> Self {
        CryptoError::Json(e)
    }
}
impl From<std::io::Error> for CryptoError {
    fn from(e: std::io::Error) -> Self {
        CryptoError::Io(e)
    }
}

/// The encrypt/decrypt boundary. A device authors an E2E op with
/// `cipher.encrypt(plaintext)` as its payload; a peer holding the key recovers
/// it with `cipher.decrypt(&op.payload)`. Object-safe so a daemon can hold an
/// `Arc<dyn PayloadCipher>` (a null/local reference now, a login-derived key
/// later) without a type change.
pub trait PayloadCipher: Send + Sync {
    /// Encrypt a cleartext payload into a ciphertext [`Envelope`] (as a
    /// `Value`).
    fn encrypt(&self, plaintext: &Value) -> Result<Value, CryptoError>;
    /// Recover the cleartext payload from a ciphertext [`Envelope`]. Fails
    /// ([`CryptoError::Decrypt`]) on a wrong key or any tamper.
    fn decrypt(&self, envelope: &Value) -> Result<Value, CryptoError>;
}

/// The single-user reference cipher: a local 256-bit ChaCha20-Poly1305 key.
///
/// Genuinely linearizable-free confidentiality + integrity for the personal
/// multi-device case. NOT a login-derived or org-distributed key — see the
/// module's key-distribution follow-up.
#[derive(Clone)]
pub struct LocalKeyCipher {
    key: [u8; 32],
}

impl Drop for LocalKeyCipher {
    fn drop(&mut self) {
        // Wipe the key on drop. Load-bearing for the org-key path: an org wrap key
        // and (transitively) K_org get copied into a `LocalKeyCipher` via
        // `from_key(*wrap_key)`, so the `Zeroizing` wrapper on the source no longer
        // covers this copy — this Drop does. (Also the first org-SHARED subkey to
        // live in a cache; blast radius is every member.)
        self.key.zeroize();
    }
}

impl std::fmt::Debug for LocalKeyCipher {
    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
        // Never print the key.
        f.debug_struct("LocalKeyCipher").finish_non_exhaustive()
    }
}

impl LocalKeyCipher {
    /// Build a cipher over an explicit 256-bit key.
    pub fn from_key(key: [u8; 32]) -> Self {
        Self { key }
    }

    /// Mint a fresh random key (OS CSPRNG). Not persisted — pair with
    /// [`Self::key_hex`] to store it, or use [`Self::load_or_generate`].
    pub fn generate() -> Self {
        let key = ChaCha20Poly1305::generate_key(&mut OsRng);
        Self { key: key.into() }
    }

    /// The key as 64 hex chars (for persistence). Handle as a secret.
    pub fn key_hex(&self) -> String {
        to_hex(&self.key)
    }

    /// Parse a 64-hex-char key.
    pub fn from_key_hex(hex: &str) -> Result<Self, CryptoError> {
        let bytes = from_hex(hex).map_err(CryptoError::Key)?;
        let key: [u8; 32] = bytes
            .try_into()
            .map_err(|_| CryptoError::Key("key must be 32 bytes (64 hex chars)".into()))?;
        Ok(Self { key })
    }

    /// Load the key from `path`, or mint + persist a new one there (`0600` on
    /// unix). The single-user "the key lives on my devices" story — a device
    /// gets the key out of band (copy the file / a recovery phrase); this is
    /// the local reference, not the login-derived distribution (the follow-up).
    pub fn load_or_generate(path: &Path) -> Result<Self, CryptoError> {
        if path.exists() {
            let hex = std::fs::read_to_string(path)?;
            return Self::from_key_hex(hex.trim());
        }
        let cipher = Self::generate();
        if let Some(parent) = path.parent() {
            std::fs::create_dir_all(parent)?;
        }
        // Create the key file 0600 from the FIRST byte (review): a
        // `write` + later `chmod` leaves the 256-bit AEAD key in a
        // world-readable file for the window between the two syscalls,
        // and a swallowed chmod error would leave it 0600-claimed but
        // 0644-real forever. `create_new` also refuses a symlink/TOCTOU
        // swap at the path. The chmod failure is surfaced, never
        // discarded.
        #[cfg(unix)]
        {
            use std::io::Write;
            use std::os::unix::fs::OpenOptionsExt;
            let mut f = std::fs::OpenOptions::new()
                .write(true)
                .create_new(true)
                .mode(0o600)
                .open(path)?;
            f.write_all(cipher.key_hex().as_bytes())?;
            f.sync_all()?;
        }
        #[cfg(not(unix))]
        {
            std::fs::write(path, cipher.key_hex())?;
            // Unix set the mode via create_new(...).mode(0o600); on Windows lock
            // the E2E key file owner-only via ACL. No-op off Windows.
            car_secrets::harden_owner_only(path);
        }
        Ok(cipher)
    }

    fn aead(&self) -> ChaCha20Poly1305 {
        ChaCha20Poly1305::new(Key::from_slice(&self.key))
    }
}

impl PayloadCipher for LocalKeyCipher {
    fn encrypt(&self, plaintext: &Value) -> Result<Value, CryptoError> {
        let bytes = serde_json::to_vec(plaintext)?;
        let nonce = ChaCha20Poly1305::generate_nonce(&mut OsRng);
        let ct = self
            .aead()
            .encrypt(&nonce, bytes.as_ref())
            .map_err(|_| CryptoError::Decrypt)?;
        let env = Envelope {
            car_enc: ALG_CHACHA20POLY1305.to_string(),
            nonce: to_hex(nonce.as_slice()),
            ct: to_hex(&ct),
            // Personal / single-key cipher: no epoch key-id (omitted on the wire).
            kid: None,
        };
        Ok(serde_json::to_value(env)?)
    }

    fn decrypt(&self, envelope: &Value) -> Result<Value, CryptoError> {
        let env: Envelope = serde_json::from_value(envelope.clone())
            .map_err(|e| CryptoError::BadEnvelope(e.to_string()))?;
        if env.car_enc != ALG_CHACHA20POLY1305 {
            return Err(CryptoError::BadEnvelope(format!(
                "unknown algorithm tag {:?}",
                env.car_enc
            )));
        }
        let nonce_bytes = from_hex(&env.nonce).map_err(CryptoError::BadEnvelope)?;
        if nonce_bytes.len() != 12 {
            return Err(CryptoError::BadEnvelope("nonce must be 12 bytes".into()));
        }
        let ct = from_hex(&env.ct).map_err(CryptoError::BadEnvelope)?;
        let nonce = Nonce::from_slice(&nonce_bytes);
        let pt = self
            .aead()
            .decrypt(nonce, ct.as_ref())
            .map_err(|_| CryptoError::Decrypt)?;
        Ok(serde_json::from_slice(&pt)?)
    }
}

/// The ChaCha20-Poly1305 associated data binding an org payload to its exact
/// `(algorithm, audience, epoch)`. Length-prefixed + domain-tagged so the bytes
/// are injective and can't be reinterpreted under a future mode — the same
/// discipline as [`wrap_sign_transcript`]. Authenticated by the AEAD tag: a
/// tampered `car_enc`/audience/`kid` fails the open. Org path ONLY — personal
/// envelopes carry no AAD (byte-identical).
///
/// The `v2` tag aligns with the wrap transcript version; there is no v1 payload
/// AAD (the personal path has none), so don't hunt for one. All integers are
/// little-endian to match [`wrap_sign_transcript`] — one endianness crate-wide.
fn org_payload_aad(car_enc: &str, audience: &str, kid: u64) -> Vec<u8> {
    let mut a = b"car-sync:payload:v2\0".to_vec();
    let mut lp = |field: &[u8]| {
        a.extend_from_slice(&(field.len() as u64).to_le_bytes());
        a.extend_from_slice(field);
    };
    lp(car_enc.as_bytes());
    lp(audience.as_bytes());
    a.extend_from_slice(&kid.to_le_bytes());
    a
}

/// A multi-epoch org cipher: holds the per-epoch derived audience keys and, on
/// decrypt, selects EXACTLY ONE by the envelope's `kid` — it NEVER iterates the
/// keyring (no trial-decrypt / wrong-key-acceptance). Encrypt always uses the
/// NEWEST epoch held and stamps `kid`. This is what makes rotation expressible: a
/// remaining member holding {N, N+1} decrypts old ops under N and new ops under
/// N+1, deterministically. Fail-closed: an unknown `kid`, a missing `kid`, or an
/// empty keyring all error (the op stays opaque) — never a wrong key.
pub struct MultiEpochOrgCipher {
    audience: String,
    /// epoch → derived audience key (`derive_key(K_org@epoch, audience)`). BTreeMap
    /// so `.last_key_value()` is the newest epoch.
    keys: std::collections::BTreeMap<u64, Zeroizing<[u8; 32]>>,
}

impl std::fmt::Debug for MultiEpochOrgCipher {
    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
        f.debug_struct("MultiEpochOrgCipher")
            .field("audience", &self.audience)
            .field("epochs", &self.keys.keys().collect::<Vec<_>>())
            .finish_non_exhaustive()
    }
}

impl MultiEpochOrgCipher {
    /// Build over the per-epoch derived audience keys (see [`OrgAwareKeyProvider`]).
    pub fn new(
        audience: impl Into<String>,
        keys: std::collections::BTreeMap<u64, Zeroizing<[u8; 32]>>,
    ) -> Self {
        Self {
            audience: audience.into(),
            keys,
        }
    }

    fn aead_for(key: &[u8; 32]) -> ChaCha20Poly1305 {
        ChaCha20Poly1305::new(Key::from_slice(key))
    }
}

impl PayloadCipher for MultiEpochOrgCipher {
    fn encrypt(&self, plaintext: &Value) -> Result<Value, CryptoError> {
        // Newest epoch held. Empty keyring → fail closed (member holds no key).
        let (&kid, key) = self
            .keys
            .last_key_value()
            .ok_or_else(|| CryptoError::Key("org cipher has no epoch keys".into()))?;
        let bytes = serde_json::to_vec(plaintext)?;
        let nonce = ChaCha20Poly1305::generate_nonce(&mut OsRng);
        let aad = org_payload_aad(ALG_CHACHA20POLY1305, &self.audience, kid);
        let ct = Self::aead_for(key)
            .encrypt(
                &nonce,
                Payload {
                    msg: bytes.as_ref(),
                    aad: &aad,
                },
            )
            .map_err(|_| CryptoError::Decrypt)?;
        let env = Envelope {
            car_enc: ALG_CHACHA20POLY1305.to_string(),
            nonce: to_hex(nonce.as_slice()),
            ct: to_hex(&ct),
            kid: Some(kid),
        };
        Ok(serde_json::to_value(env)?)
    }

    fn decrypt(&self, envelope: &Value) -> Result<Value, CryptoError> {
        let env: Envelope = serde_json::from_value(envelope.clone())
            .map_err(|e| CryptoError::BadEnvelope(e.to_string()))?;
        if env.car_enc != ALG_CHACHA20POLY1305 {
            return Err(CryptoError::BadEnvelope(format!(
                "unknown algorithm tag {:?}",
                env.car_enc
            )));
        }
        // Org envelopes MUST carry a kid; select EXACTLY that epoch's key. No kid,
        // or a kid we don't hold → fail closed. Never iterate / trial-decrypt.
        let kid = env
            .kid
            .ok_or_else(|| CryptoError::BadEnvelope("org envelope missing epoch kid".into()))?;
        let key = self
            .keys
            .get(&kid)
            .ok_or_else(|| CryptoError::Key(format!("no org key held for epoch {kid}")))?;
        let nonce_bytes = from_hex(&env.nonce).map_err(CryptoError::BadEnvelope)?;
        if nonce_bytes.len() != 12 {
            return Err(CryptoError::BadEnvelope("nonce must be 12 bytes".into()));
        }
        let ct = from_hex(&env.ct).map_err(CryptoError::BadEnvelope)?;
        let nonce = Nonce::from_slice(&nonce_bytes);
        let aad = org_payload_aad(ALG_CHACHA20POLY1305, &self.audience, kid);
        let pt = Self::aead_for(key)
            .decrypt(
                nonce,
                Payload {
                    msg: ct.as_ref(),
                    aad: &aad,
                },
            )
            .map_err(|_| CryptoError::Decrypt)?;
        Ok(serde_json::from_slice(&pt)?)
    }
}

/// The encryption **audience** a scope maps to — the set of principals whose
/// key a payload under this scope is encrypted to. `Personal` → the user's own
/// key; `Shared{org}` → the org key. The B4-pinned rule ("scopes are
/// encryption audiences") uses this: a single ciphertext must have a single
/// audience, so a whole-chain checkpoint mixing scopes cannot be one ciphertext.
pub fn encryption_audience(scope: &Scope) -> String {
    match scope {
        Scope::Personal => "personal".to_string(),
        Scope::Shared { org } => format!("org:{org}"),
    }
}

// ---------------------------------------------------------------------------
// Login-derived key distribution (B6).
//
// A single-user reference key (`LocalKeyCipher::load_or_generate`) doesn't scale
// to "onboard once": a new device would have to copy a key file out of band.
// Instead every device HKDF-derives its per-audience AEAD keys from ONE master
// secret it gets from the Parslee login (per-user) / entitlements (per-org).
// Same login → same master → same derived keys on every device (so they decrypt
// each other), while "personal" and "org:<id>" audiences stay cryptographically
// independent. The master never leaves the authenticated client — the relay
// only ever holds ciphertext under a key it does not possess.
// ---------------------------------------------------------------------------

/// HKDF-SHA256 info prefix for CAR sync AEAD keys — bump `v1` on a KDF change.
const KDF_INFO_PREFIX: &[u8] = b"car-sync/v1/aead/";
/// A fixed (non-secret) HKDF salt. A constant makes derivation deterministic
/// across a user's devices from the same master — the whole point.
const KDF_SALT: &[u8] = b"car-sync/v1/salt";

/// Derive a 256-bit AEAD key for `audience` from a login/entitlement `master`
/// secret via HKDF-SHA256. Deterministic: the same `(master, audience)` yields
/// the same key on every device (a user's Mac and phone decrypt each other's
/// ops); distinct audiences ("personal" vs "org:<id>") yield independent keys.
pub fn derive_key(master: &[u8], audience: &str) -> [u8; 32] {
    let hk = hkdf::Hkdf::<sha2::Sha256>::new(Some(KDF_SALT), master);
    let mut info = KDF_INFO_PREFIX.to_vec();
    info.extend_from_slice(audience.as_bytes());
    let mut okm = [0u8; 32];
    hk.expand(&info, &mut okm)
        .expect("32 bytes is a valid HKDF-SHA256 output length");
    okm
}

/// The KDF profile a [`StretchedMaster`] was minted under. Versioned so that
/// RAISING the Argon2id params later is an explicit re-key epoch (it changes every
/// downstream key, so it folds into org-key rotation) — never a silent key fork.
/// A device records which profile minted its current keys.
#[derive(Clone, Copy, Debug, PartialEq, Eq, Serialize, Deserialize)]
pub enum KdfProfile {
    /// Argon2id V0x13, m=64 MiB, t=3, p=1 — the launch profile for passphrases.
    Argon2idV1,
    /// HKDF-only — a Parslee-issued ≥256-bit secret (no stretch needed).
    IssuedHkdfV1,
}

// Launch Argon2id params (OWASP-defensible; won't OOM an older phone).
const ARGON2_M_COST_KIB: u32 = 65536; // 64 MiB
const ARGON2_T_COST: u32 = 3;
const ARGON2_P_COST: u32 = 1;
/// Prefix for the DETERMINISTIC per-user Argon2id salt. Deterministic (not random)
/// so a passphrase yields the same keys on every device with no server state; the
/// salt is domain separation across users, NOT secrecy (the work factor is the
/// memory-hardness). `user_id` MUST be canonical upstream (else two spellings fork
/// keys and cross-device sync silently breaks).
const KDF_ARGON2_SALT_PREFIX: &[u8] = b"car-sync/v1/argon2-salt/user:";

fn argon2_salt(user_id: &str) -> [u8; 16] {
    let mut h = sha2::Sha256::new();
    h.update(KDF_ARGON2_SALT_PREFIX);
    h.update(user_id.as_bytes());
    let digest = h.finalize();
    let mut salt = [0u8; 16];
    salt.copy_from_slice(&digest[..16]);
    salt
}

/// A high-entropy 32-byte master for ALL of a user's key derivations — the
/// per-audience AEAD keys AND the X25519/Ed25519 identities derive from THIS (via
/// HKDF), never from a raw passphrase. The type is the gate: an identity or
/// audience key cannot be derived from an unstretched password, because those
/// functions take `&StretchedMaster`, and the only ways to build one are the two
/// constructors below.
pub struct StretchedMaster {
    bytes: Zeroizing<[u8; 32]>,
    profile: KdfProfile,
}

impl std::fmt::Debug for StretchedMaster {
    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
        f.debug_struct("StretchedMaster")
            .field("profile", &self.profile)
            .finish_non_exhaustive()
    }
}

impl StretchedMaster {
    /// Argon2id-stretch a (password-equivalent) passphrase into the master,
    /// deterministically per user (see [`argon2_salt`]).
    ///
    /// SECURITY — mitigation, NOT closure: this raises the per-guess cost of a weak
    /// passphrase but cannot mint entropy it never had. The user's identity PUBLIC
    /// key is published (the platform maps `account_id → pubkey`), which is an
    /// OFFLINE verification oracle — an attacker guesses a passphrase, stretches,
    /// derives, and compares to the published key with NO network. Argon2id's
    /// per-guess cost is then the entire wall; a short password still falls. A PAKE
    /// removes the oracle and is the strictly stronger path. Passphrase policy,
    /// param benchmarking, and the PAKE alternative still require a cryptographer
    /// before production.
    pub fn from_passphrase(passphrase: &[u8], user_id: &str) -> Self {
        let salt = argon2_salt(user_id);
        let params = argon2::Params::new(ARGON2_M_COST_KIB, ARGON2_T_COST, ARGON2_P_COST, Some(32))
            .expect("fixed Argon2idV1 params are valid");
        let argon =
            argon2::Argon2::new(argon2::Algorithm::Argon2id, argon2::Version::V0x13, params);
        let mut bytes = Zeroizing::new([0u8; 32]);
        argon
            .hash_password_into(passphrase, &salt, bytes.as_mut_slice())
            .expect("argon2 with valid params + 32-byte output does not fail");
        Self {
            bytes,
            profile: KdfProfile::Argon2idV1,
        }
    }

    /// From a Parslee-issued high-entropy secret (the caller CERTIFIES it is
    /// ≥256-bit). Skips Argon2id — stretching a strong key is pointless cost —
    /// and HKDF-binds it to `user_id` for per-user domain separation.
    pub fn from_issued_high_entropy(secret: &[u8], user_id: &str) -> Self {
        Self {
            bytes: Zeroizing::new(derive_key(secret, &format!("user/{user_id}"))),
            profile: KdfProfile::IssuedHkdfV1,
        }
    }

    /// The profile that minted this master (for the rotation/migration machinery).
    pub fn profile(&self) -> KdfProfile {
        self.profile
    }

    fn as_bytes(&self) -> &[u8; 32] {
        &self.bytes
    }
}

/// Supplies the [`PayloadCipher`] for a scope's encryption audience. The daemon
/// holds one and asks for a cipher per op-scope, so a remote relay only ever
/// sees ciphertext under the right (personal / org) key.
pub trait SyncKeyProvider: Send + Sync {
    fn cipher_for(&self, scope: &Scope) -> std::sync::Arc<dyn PayloadCipher>;
}

/// Derives per-audience [`LocalKeyCipher`]s from one login-derived master secret
/// (HKDF-SHA256), caching by audience. The master comes from the Parslee login
/// (per-user) / entitlements (per-org); it is NEVER sent to the relay.
pub struct DerivedKeyProvider {
    master: Zeroizing<Vec<u8>>,
    cache: std::sync::Mutex<std::collections::HashMap<String, std::sync::Arc<LocalKeyCipher>>>,
}

impl std::fmt::Debug for DerivedKeyProvider {
    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
        f.debug_struct("DerivedKeyProvider").finish_non_exhaustive()
    }
}

impl DerivedKeyProvider {
    /// Build over a raw 32-byte master (already high-entropy + stable across the
    /// user's devices). Prefer [`Self::from_master`] with a [`StretchedMaster`].
    pub fn new(master: impl Into<Vec<u8>>) -> Self {
        Self {
            master: Zeroizing::new(master.into()),
            cache: std::sync::Mutex::new(std::collections::HashMap::new()),
        }
    }

    /// Build the per-audience AEAD keys from a [`StretchedMaster`] — the same
    /// master that mints the identity keys, so Argon2id runs ONCE at open and both
    /// paths share it.
    pub fn from_master(master: &StretchedMaster) -> Self {
        Self::new(master.as_bytes().to_vec())
    }

    /// Build from a Parslee-issued high-entropy secret bound to `user_id` (no
    /// Argon2id — the secret is already strong). The issued-key alternative to a
    /// passphrase; both converge on a [`StretchedMaster`].
    pub fn from_login_secret(login_secret: &[u8], user_id: &str) -> Self {
        Self::from_master(&StretchedMaster::from_issued_high_entropy(
            login_secret,
            user_id,
        ))
    }

    /// Build from a user **sync passphrase** — the zero-knowledge cross-device key
    /// source that needs NO server key distribution: every device on which the
    /// user enters the same passphrase derives the same keys, and Parslee (relay +
    /// platform) never sees it. The passphrase is Argon2id-STRETCHED (see
    /// [`StretchedMaster::from_passphrase`]) before any key derivation.
    pub fn from_passphrase(passphrase: &str, user_id: &str) -> Self {
        Self::from_master(&StretchedMaster::from_passphrase(
            passphrase.as_bytes(),
            user_id,
        ))
    }

    fn cipher_for_audience(&self, audience: &str) -> std::sync::Arc<dyn PayloadCipher> {
        let mut cache = self.cache.lock().expect("key cache poisoned");
        if let Some(c) = cache.get(audience) {
            return c.clone();
        }
        let cipher = std::sync::Arc::new(LocalKeyCipher::from_key(derive_key(
            self.master.as_slice(),
            audience,
        )));
        cache.insert(audience.to_string(), cipher.clone());
        cipher
    }
}

impl SyncKeyProvider for DerivedKeyProvider {
    fn cipher_for(&self, scope: &Scope) -> std::sync::Arc<dyn PayloadCipher> {
        self.cipher_for_audience(&encryption_audience(scope))
    }
}

pub(crate) fn to_hex(bytes: &[u8]) -> String {
    bytes.iter().map(|b| format!("{b:02x}")).collect()
}

pub(crate) fn from_hex(s: &str) -> Result<Vec<u8>, String> {
    if !s.len().is_multiple_of(2) {
        return Err("hex length must be even".into());
    }
    (0..s.len())
        .step_by(2)
        .map(|i| u8::from_str_radix(&s[i..i + 2], 16).map_err(|e| e.to_string()))
        .collect()
}

// ---------------------------------------------------------------------------
// Client-side ORG-key agreement (ECIES over X25519).
//
// The gap this closes: `DerivedKeyProvider` derives the org audience from each
// member's OWN login master, so members end up with DIFFERENT org keys and
// cannot read each other's org-scoped ops. The fix is a SHARED org master key
// `K_org` that every member obtains — but the relay/platform must NEVER see it.
//
// So `K_org` is wrapped for each member with public-key encryption (ECIES): a
// fresh ephemeral X25519 exchange to the member's identity key, HKDF over the
// shared secret WITH THE FULL TRANSCRIPT BOUND (org, epoch, recipient, both
// public keys), then the existing AEAD. The relay stores only the wrapped blob;
// only the member's identity secret unwraps it. Established primitives, standard
// construction — nothing invented.
//
// SECURITY — MUST be reviewed by a cryptographer before production:
//   * the login_secret → identity derivation (see `derive_x25519_identity`);
//   * whether org/epoch also belong in the AEAD AAD (not only the HKDF info);
//   * secret zeroization + at-rest protection of the identity secret;
//   * rotation-under-compromise and key recovery/escrow.
// This module gives the pure wrap/unwrap + identity primitive; the relay org-key
// surface, the oplog epoch field, rotation orchestration, and the
// `SyncKeyProvider` swap-in are follow-ups.
// ---------------------------------------------------------------------------

/// HKDF info prefix for the deterministic per-user X25519 identity key. Its OWN
/// namespace — an asymmetric identity key must not share the `derive_key`
/// (`.../aead/`) domain-separation namespace with the symmetric AEAD keys.
const KDF_INFO_X25519_ID: &[u8] = b"car-sync/v1/x25519-identity/v1/user:";
/// HKDF domain for the Ed25519 SIGNING identity. DISTINCT label from the X25519
/// identity domain above — HKDF-expand with different `info` yields independent
/// sibling subkeys (no key reuse between the DH key and the signing key). The two
/// labels must never collide.
const KDF_INFO_ED25519_ID: &[u8] = b"car-sync/v1/ed25519-identity/v1/user:";

/// Wire tag for a wrapped org-key blob. **v2** adds the publisher signature:
/// every wrap is signed by the publisher's Ed25519 identity, and [`unwrap_org_key`]
/// REFUSES any wrap not signed by a caller-trusted holder — closing the key
/// SUBSTITUTION hole (v1 sealed a key TO a recipient but authenticated NO ONE, so
/// any member could wrap an attacker-chosen `K_org'` to a victim). There is NO v1
/// accept path in live unwrap: a downgrade to an unsigned wrap is structurally
/// impossible, not policy-gated.
pub const ALG_ORG_KEY_WRAP: &str = "org-key-wrap/v2";

/// Derive a user's deterministic X25519 identity secret from their
/// [`StretchedMaster`], so every device reconstructs the SAME keypair (the public
/// key is published; the secret never leaves the device). 32 bytes of HKDF-SHA256
/// output are a valid X25519 scalar (dalek clamps at DH time).
///
/// Takes a `&StretchedMaster` (not raw bytes) BY DESIGN: a password-equivalent
/// passphrase must be Argon2id-stretched first (the memory-hard work factor the
/// audit required), and the type forbids feeding an unstretched password here.
/// SECURITY residual: the published public key is still an offline guessing oracle
/// — see [`StretchedMaster::from_passphrase`]. Cryptographer review still required.
pub fn derive_x25519_identity(master: &StretchedMaster, user_id: &str) -> StaticSecret {
    let hk = hkdf::Hkdf::<sha2::Sha256>::new(Some(KDF_SALT), master.as_bytes());
    let mut info = KDF_INFO_X25519_ID.to_vec();
    info.extend_from_slice(user_id.as_bytes());
    let mut sk = [0u8; 32];
    hk.expand(&info, &mut sk)
        .expect("32 is a valid HKDF-SHA256 output length");
    let secret = StaticSecret::from(sk);
    sk.zeroize();
    secret
}

/// The publishable public identity for a user (the platform maps
/// `account_id → this` so a wrapper can find each member's key).
pub fn x25519_public(secret: &StaticSecret) -> PublicKey {
    PublicKey::from(secret)
}

/// Derive a user's deterministic Ed25519 SIGNING identity from their
/// [`StretchedMaster`], under a domain distinct from the X25519 identity (see
/// [`KDF_INFO_ED25519_ID`]). The publisher signs each wrap with this key so a
/// recipient can reject wraps not authored by a trusted holder. The verifying key
/// ([`ed25519_verifying`]) is published beside the X25519 public key.
///
/// Takes a `&StretchedMaster` for the same reason as [`derive_x25519_identity`] —
/// the Argon2id stretch is enforced by the type, and the same offline-oracle
/// residual applies.
pub fn derive_ed25519_identity(master: &StretchedMaster, user_id: &str) -> SigningKey {
    let hk = hkdf::Hkdf::<sha2::Sha256>::new(Some(KDF_SALT), master.as_bytes());
    let mut info = KDF_INFO_ED25519_ID.to_vec();
    info.extend_from_slice(user_id.as_bytes());
    let mut seed = [0u8; 32];
    hk.expand(&info, &mut seed)
        .expect("32 is a valid HKDF-SHA256 output length");
    let signing = SigningKey::from_bytes(&seed);
    seed.zeroize();
    signing
}

/// The publishable Ed25519 verifying key for a signing identity.
pub fn ed25519_verifying(signing: &SigningKey) -> VerifyingKey {
    signing.verifying_key()
}

/// An org id usable in a wrap: rejected (never rewritten) unless it is a strict
/// ASCII slug `[A-Za-z0-9._-]+`. This blocks Unicode confusables and
/// delimiter-injection at the crypto boundary and pins the exact bytes bound into
/// BOTH the KDF transcript and the signature — so a caller cannot sign a different
/// transcript for "Acme" than for "acme". Case-folding is deliberately NOT done
/// here (the Turkish-İ / locale trap is itself a canonicalization bypass); the
/// platform MUST mint ONE canonical opaque org id upstream (a tenant id), and this
/// only enforces that it is well-formed and bound verbatim.
pub fn require_canonical_org(org: &str) -> Result<(), CryptoError> {
    if org.is_empty() {
        return Err(CryptoError::Key("org id is empty".into()));
    }
    if !org
        .bytes()
        .all(|b| b.is_ascii_alphanumeric() || matches!(b, b'.' | b'_' | b'-'))
    {
        return Err(CryptoError::Key(format!(
            "org id {org:?} is not a canonical ASCII slug [A-Za-z0-9._-]"
        )));
    }
    Ok(())
}

/// The HKDF info that binds the FULL transcript of a wrap — org, epoch,
/// recipient, the ephemeral pubkey, and the recipient pubkey. Binding all five
/// makes each wrap blob non-transplantable across members/epochs/orgs and pins
/// it to this exact exchange: a substituted `E` or `P` derives a different key,
/// so the AEAD open fails. Under-binding here passes every functional test while
/// silently breaking security — so it is bound in exactly one place, here.
///
/// The embedded `org-key-wrap/v1` label is the KDF-CONSTRUCTION version and is
/// deliberately FROZEN — decoupled from the `v2` wire tag ([`ALG_ORG_KEY_WRAP`]).
/// v1→v2 only ADDED the signature layer; the ECIES/KDF derivation is unchanged, so
/// bumping this label would gratuitously break key derivation for no benefit.
fn org_wrap_info(
    org: &str,
    epoch: u64,
    recipient_user_id: &str,
    e_pub: &PublicKey,
    p_pub: &PublicKey,
) -> String {
    // LENGTH-PREFIX the free-form fields (`org`, `recipient_user_id`) so the
    // transcript is injective: a reader consumes exactly N bytes after `=N:`, so
    // no (org, epoch, recipient) tuple can collide with another via delimiter
    // injection (e.g. an org id containing "/recipient:..."). Naive `/`+`:`
    // interpolation is NOT injective when the ids are attacker-influenced.
    // `epoch` is decimal-only and `E`/`P` are fixed-width hex, so they're safe.
    format!(
        "org-key-wrap/v1|org={}:{}|epoch={}|recipient={}:{}|E={}|P={}",
        org.len(),
        org,
        epoch,
        recipient_user_id.len(),
        recipient_user_id,
        to_hex(e_pub.as_bytes()),
        to_hex(p_pub.as_bytes()),
    )
}

/// The exact bytes the publisher SIGNS. Binds every field + the AEAD envelope +
/// the publisher id, so no field/ciphertext is substitutable under a copied
/// signature and the wrap is attributed non-repudiably to `publisher`. Each
/// variable-length field is length-prefixed (8-byte LE) so the encoding is
/// injective; `epoch` is fixed-width. The alg tag is included so a v2 signature
/// can never be replayed under another version. Signs the AEAD ENVELOPE (its
/// canonical JSON — nonce+ct+tag), NOT the plaintext. NOTE: what defends against
/// key substitution is the SIGNATURE plus the per-wrap unique key (a fresh
/// ephemeral DH → a distinct `wrap_key` per blob, and each blob is
/// single-recipient) — NOT any commitment property of the AEAD: ChaCha20-Poly1305
/// is NOT key-committing (Poly1305 is not collision-resistant on the key). Signing
/// the ciphertext is sufficient here because the signature binds it; do not
/// refactor this to lean on "the AEAD commits `k_org`" — it does not.
fn wrap_sign_transcript(
    org: &str,
    epoch: u64,
    recipient_user_id: &str,
    publisher_user_id: &str,
    e_pub: &PublicKey,
    p_pub: &PublicKey,
    envelope: &Value,
) -> Vec<u8> {
    fn lp(buf: &mut Vec<u8>, field: &[u8]) {
        buf.extend_from_slice(&(field.len() as u64).to_le_bytes());
        buf.extend_from_slice(field);
    }
    let mut t = Vec::new();
    lp(&mut t, ALG_ORG_KEY_WRAP.as_bytes());
    lp(&mut t, org.as_bytes());
    t.extend_from_slice(&epoch.to_le_bytes());
    lp(&mut t, recipient_user_id.as_bytes());
    lp(&mut t, publisher_user_id.as_bytes());
    lp(&mut t, e_pub.as_bytes());
    lp(&mut t, p_pub.as_bytes());
    lp(&mut t, canonical_json(envelope).as_bytes());
    t
}

/// A shared org master key wrapped for one member — AUTHENTICATED ECIES over
/// X25519. Sealed to the member's X25519 key (only their secret unwraps it) AND
/// signed by the publisher's Ed25519 identity (only a caller-trusted publisher is
/// accepted). Every member unwraps the SAME `k_org` and derives the org-audience
/// AEAD key from it, so org-scoped ops become mutually readable.
#[derive(Debug, Clone, PartialEq, Serialize, Deserialize)]
pub struct WrappedOrgKey {
    /// Algorithm tag ([`ALG_ORG_KEY_WRAP`], "org-key-wrap/v2").
    pub car_wrap: String,
    pub org: String,
    /// The key-rotation epoch this `k_org` belongs to (member removal bumps it).
    pub epoch: u64,
    /// The member this blob is addressed to. ADVISORY ONLY — not
    /// integrity-protected for ROUTING: unwrap binds the CALLER's own `my_user_id`
    /// into both the KDF and the signature transcript, not this field. Do not
    /// route or authorize on it.
    pub recipient: String,
    /// The publisher (signer) user id. ADVISORY — a routing/label hint. unwrap
    /// authorizes on the injected TRUSTED verifying-key set, NEVER on this field.
    pub publisher: String,
    /// Ephemeral X25519 public key (hex) — re-fed into the KDF on unwrap.
    pub ephemeral_pub: String,
    /// Recipient's X25519 public key (hex) — bound into the KDF.
    pub recipient_pub: String,
    /// AEAD envelope over `{ "k_org": <hex> }`.
    pub envelope: Value,
    /// Ed25519 signature (hex, 64 bytes) by the publisher over
    /// [`wrap_sign_transcript`]. Verified with `verify_strict` against a trusted
    /// key on unwrap, BEFORE any decrypt.
    pub signature: String,
}

/// Mint a fresh org master key `K_org` from the OS CSPRNG. Returned in
/// [`Zeroizing`] so it wipes on drop.
///
/// CRITICAL for rotation: a NEW epoch's `K_org` MUST come from here — an
/// independent random draw — NEVER a hash/KDF chain from the previous epoch's
/// key. A removed member still holds the old `K_org`; if `K_org@(N+1)` were any
/// function of `K_org@N`, they could derive the new key and rotation would be
/// theatre. There is deliberately no `derive_next_org_key(old)` API.
pub fn generate_org_key() -> Zeroizing<[u8; 32]> {
    Zeroizing::new(ChaCha20Poly1305::generate_key(&mut OsRng).into())
}

/// Wrap the shared org master key `k_org` for `recipient_pub` in `(org, epoch)`,
/// SIGNED by `publisher_user_id`'s `signer`. A fresh ephemeral keypair per wrap;
/// the full transcript is bound into the KDF; a low-order (degenerate) recipient
/// key is rejected via the contributory check; the whole blob (incl. the AEAD
/// envelope + publisher id) is signed so a recipient can reject wraps not authored
/// by a trusted holder. `org` must be a canonical ASCII slug (see
/// [`require_canonical_org`]).
pub fn wrap_org_key(
    k_org: &[u8; 32],
    org: &str,
    epoch: u64,
    recipient_user_id: &str,
    recipient_pub: &PublicKey,
    publisher_user_id: &str,
    signer: &SigningKey,
) -> Result<WrappedOrgKey, CryptoError> {
    require_canonical_org(org)?;
    // Fresh ephemeral keypair (reuse the OS-CSPRNG path the AEAD already uses).
    let mut e_bytes: [u8; 32] = ChaCha20Poly1305::generate_key(&mut OsRng).into();
    let e_secret = StaticSecret::from(e_bytes);
    e_bytes.zeroize();
    let e_pub = PublicKey::from(&e_secret);

    let shared = e_secret.diffie_hellman(recipient_pub);
    if !shared.was_contributory() {
        // Low-order / degenerate recipient key → all-zero shared secret. Refuse
        // (dalek does NOT reject it for us).
        return Err(CryptoError::Key(
            "recipient public key is low-order (non-contributory DH)".into(),
        ));
    }
    let wrap_key = zeroize::Zeroizing::new(derive_key(
        shared.as_bytes(),
        &org_wrap_info(org, epoch, recipient_user_id, &e_pub, recipient_pub),
    ));
    let envelope = LocalKeyCipher::from_key(*wrap_key).encrypt(&serde_json::json!({
        "k_org": to_hex(k_org),
    }))?;
    // Sign the whole transcript (fields + envelope + publisher id).
    let signature = signer.sign(&wrap_sign_transcript(
        org,
        epoch,
        recipient_user_id,
        publisher_user_id,
        &e_pub,
        recipient_pub,
        &envelope,
    ));
    Ok(WrappedOrgKey {
        car_wrap: ALG_ORG_KEY_WRAP.to_string(),
        org: org.to_string(),
        epoch,
        recipient: recipient_user_id.to_string(),
        publisher: publisher_user_id.to_string(),
        ephemeral_pub: to_hex(e_pub.as_bytes()),
        recipient_pub: to_hex(recipient_pub.as_bytes()),
        envelope,
        signature: to_hex(&signature.to_bytes()),
    })
}

/// Unwrap a [`WrappedOrgKey`] addressed to this member with their identity
/// secret — ONLY if it is signed by a key in `trusted`. Order is
/// verify-BEFORE-decrypt: the signature (over the full transcript, bound to THIS
/// caller's `my_user_id`) is checked with `verify_strict` against each trusted
/// verifying key FIRST; if none accept it, the blob is refused and no decrypt
/// runs. Then the transcript-bound key is re-derived from the PUBLIC blob and
/// `my_user_id`, so a wrong recipient / tampered ephemeral or recipient pubkey /
/// altered org/epoch also yield a different key and the AEAD open fails.
///
/// `trusted` is the caller's policy — the set of holders authorized to grant this
/// org's key (admin-designated granters; NOT all current holders). The blob's
/// advisory `publisher`/`recipient` fields are NEVER authorized on. There is no
/// v1 (unsigned) accept path — a downgrade is structurally impossible.
pub fn unwrap_org_key(
    wrapped: &WrappedOrgKey,
    my_secret: &StaticSecret,
    my_user_id: &str,
    trusted: &[VerifyingKey],
) -> Result<[u8; 32], CryptoError> {
    if wrapped.car_wrap != ALG_ORG_KEY_WRAP {
        return Err(CryptoError::BadEnvelope(format!(
            "unknown wrap tag {:?} (expected {ALG_ORG_KEY_WRAP})",
            wrapped.car_wrap
        )));
    }
    require_canonical_org(&wrapped.org)?;
    let e_pub = parse_x25519_pub(&wrapped.ephemeral_pub)?;
    let recipient_pub = parse_x25519_pub(&wrapped.recipient_pub)?;

    // AUTHENTICATE FIRST — reject any wrap not signed by a trusted holder, before
    // touching the DH / AEAD. The transcript binds MY user id (not the blob's
    // advisory recipient), so a wrap the publisher signed for a DIFFERENT
    // recipient won't verify here.
    let sig_bytes: [u8; 64] = from_hex(&wrapped.signature)
        .map_err(CryptoError::Key)?
        .try_into()
        .map_err(|_| CryptoError::Key("signature must be 64 bytes".into()))?;
    let signature = Signature::from_bytes(&sig_bytes);
    let transcript = wrap_sign_transcript(
        &wrapped.org,
        wrapped.epoch,
        my_user_id,
        &wrapped.publisher,
        &e_pub,
        &recipient_pub,
        &wrapped.envelope,
    );
    let authenticated = trusted
        .iter()
        .any(|vk| vk.verify_strict(&transcript, &signature).is_ok());
    if !authenticated {
        return Err(CryptoError::Key(
            "wrap is not signed by any trusted holder — refusing (possible key substitution)"
                .into(),
        ));
    }

    let shared = my_secret.diffie_hellman(&e_pub);
    if !shared.was_contributory() {
        return Err(CryptoError::Key(
            "ephemeral public key is low-order (non-contributory DH)".into(),
        ));
    }
    // Bind OUR user id (not the blob's claimed recipient): a blob is unwrappable
    // only if its wrapper used this exact user id AND our secret matches the
    // bound recipient pubkey.
    let wrap_key = zeroize::Zeroizing::new(derive_key(
        shared.as_bytes(),
        &org_wrap_info(
            &wrapped.org,
            wrapped.epoch,
            my_user_id,
            &e_pub,
            &recipient_pub,
        ),
    ));
    let pt = LocalKeyCipher::from_key(*wrap_key).decrypt(&wrapped.envelope)?;
    let k_hex = pt
        .get("k_org")
        .and_then(Value::as_str)
        .ok_or_else(|| CryptoError::BadEnvelope("wrapped payload missing k_org".into()))?;
    let bytes = from_hex(k_hex).map_err(CryptoError::Key)?;
    bytes
        .try_into()
        .map_err(|_| CryptoError::Key("k_org must be 32 bytes".into()))
}

/// Parse a 64-hex-char X25519 public key — e.g. a member's published identity
/// pubkey ([`crate::org_key_directory::MemberPublicKey::public_hex`]) that a
/// granter wraps `K_org` against.
///
/// This validates ONLY the encoding (32 bytes of hex); it does NOT reject a
/// low-order / non-contributory point (`PublicKey::from([u8;32])` is infallible).
/// That rejection happens later, at wrap time, via `wrap_org_key`'s contributory
/// DH check — so callers must treat a successful parse as "well-encoded", not
/// "safe to wrap to".
pub fn parse_x25519_pub(hex: &str) -> Result<PublicKey, CryptoError> {
    let bytes = from_hex(hex).map_err(CryptoError::Key)?;
    let arr: [u8; 32] = bytes
        .try_into()
        .map_err(|_| CryptoError::Key("x25519 public key must be 32 bytes".into()))?;
    Ok(PublicKey::from(arr))
}

/// Parse a 64-hex-char Ed25519 verifying (public) key — e.g. a configured trusted
/// granter key for the `trusted` set of [`unwrap_org_key`]. Rejects a bad length
/// or a non-canonical / small-order point (`VerifyingKey::from_bytes` validates).
pub fn parse_ed25519_verifying(hex: &str) -> Result<VerifyingKey, CryptoError> {
    let bytes = from_hex(hex).map_err(CryptoError::Key)?;
    let arr: [u8; 32] = bytes
        .try_into()
        .map_err(|_| CryptoError::Key("ed25519 verifying key must be 32 bytes".into()))?;
    VerifyingKey::from_bytes(&arr)
        .map_err(|e| CryptoError::Key(format!("invalid ed25519 verifying key: {e}")))
}

#[cfg(test)]
mod org_key_tests {
    use super::*;
    use serde_json::json;

    // Fast identity helpers for tests: issued-high-entropy (skips Argon2id) so the
    // suite stays fast, then the real derivation. Same `(secret, user)` shape as
    // the old raw-bytes fns, so the call sites below are a pure rename.
    fn x25519_id(secret: &[u8], user: &str) -> StaticSecret {
        crate::crypto::derive_x25519_identity(
            &StretchedMaster::from_issued_high_entropy(secret, user),
            user,
        )
    }
    fn ed25519_id(secret: &[u8], user: &str) -> SigningKey {
        crate::crypto::derive_ed25519_identity(
            &StretchedMaster::from_issued_high_entropy(secret, user),
            user,
        )
    }

    // A trusted granter — the admin-designated holder authorized to grant this
    // org's key. Its verifying key is the recipient's `trusted` policy.
    fn granter() -> SigningKey {
        ed25519_id(b"granter-login-secret", "acc_granter")
    }
    fn trusted() -> Vec<VerifyingKey> {
        vec![ed25519_verifying(&granter())]
    }
    // Wrap authored by the trusted granter (the common happy-path publisher).
    fn wrap_by_granter(
        k_org: &[u8; 32],
        org: &str,
        epoch: u64,
        recipient: &str,
        recipient_pub: &PublicKey,
    ) -> WrappedOrgKey {
        wrap_org_key(
            k_org,
            org,
            epoch,
            recipient,
            recipient_pub,
            "acc_granter",
            &granter(),
        )
        .unwrap()
    }

    #[test]
    fn org_key_wrap_round_trips_for_the_recipient() {
        let alice = x25519_id(b"alice-login-secret", "acc_alice");
        let k_org = [7u8; 32];
        let wrapped = wrap_by_granter(&k_org, "acme", 1, "acc_alice", &x25519_public(&alice));
        assert_eq!(
            unwrap_org_key(&wrapped, &alice, "acc_alice", &trusted()).unwrap(),
            k_org
        );
    }

    #[test]
    fn substitution_by_untrusted_publisher_is_refused() {
        // THE FIX. Mallory is a real org member (so the backend lets her publish),
        // and she seals an attacker-chosen K_org' to Alice's REAL pubkey — the
        // AEAD would open fine. But Mallory's signing key is NOT in Alice's trusted
        // set, so unwrap refuses BEFORE decrypting. Under v1 Alice would have
        // adopted the attacker's key.
        let alice = x25519_id(b"alice", "acc_alice");
        let mallory = ed25519_id(b"mallory-login", "acc_mallory");
        let k_org_evil = [0xEEu8; 32];
        let poisoned = wrap_org_key(
            &k_org_evil,
            "acme",
            1,
            "acc_alice",
            &x25519_public(&alice),
            "acc_mallory",
            &mallory,
        )
        .unwrap();
        let err = unwrap_org_key(&poisoned, &alice, "acc_alice", &trusted()).unwrap_err();
        assert!(matches!(err, CryptoError::Key(_)));
        // ...and it WOULD have opened if Mallory were trusted (proves the AEAD
        // itself doesn't distinguish the keys — only the signature policy does).
        let mallory_trusted = vec![ed25519_verifying(&mallory)];
        assert_eq!(
            unwrap_org_key(&poisoned, &alice, "acc_alice", &mallory_trusted).unwrap(),
            k_org_evil
        );
    }

    #[test]
    fn wrap_for_a_different_recipient_cannot_be_replayed() {
        // The granter signs a wrap FOR bob; alice (trusting the granter) must not
        // be able to unwrap it as herself — the signature transcript binds the
        // recipient, and unwrap rebuilds it with the CALLER's id.
        let alice = x25519_id(b"alice", "acc_alice");
        let bob = x25519_id(b"bob", "acc_bob");
        let for_bob = wrap_by_granter(&[9u8; 32], "acme", 1, "acc_bob", &x25519_public(&bob));
        assert!(unwrap_org_key(&for_bob, &alice, "acc_alice", &trusted()).is_err());
    }

    #[test]
    fn org_key_does_not_unwrap_for_a_different_member_or_id() {
        let alice = x25519_id(b"alice-secret", "acc_alice");
        let bob = x25519_id(b"bob-secret", "acc_bob");
        let k_org = [9u8; 32];
        let wrapped = wrap_by_granter(&k_org, "acme", 1, "acc_alice", &x25519_public(&alice));
        // Bob's secret can't unwrap Alice's blob (and his id fails the sig transcript).
        assert!(unwrap_org_key(&wrapped, &bob, "acc_bob", &trusted()).is_err());
        // Nor can Alice unwrap it while claiming a different id (id binding).
        assert!(unwrap_org_key(&wrapped, &alice, "acc_bob", &trusted()).is_err());
    }

    #[test]
    fn org_key_unwrap_rejects_tampered_transcript_and_ciphertext() {
        let alice = x25519_id(b"alice-secret", "acc_alice");
        let k_org = [3u8; 32];
        let base = wrap_by_granter(&k_org, "acme", 1, "acc_alice", &x25519_public(&alice));
        let bob_pub = x25519_public(&x25519_id(b"bob", "acc_bob"));
        let unwrap = |t: &WrappedOrgKey| unwrap_org_key(t, &alice, "acc_alice", &trusted());

        // Every field is under the signature now — any tamper fails verify first.
        // Tamper the AEAD ciphertext (flip the last hex char).
        let mut t = base.clone();
        let ct = t.envelope["ct"].as_str().unwrap().to_string();
        let mut chars: Vec<char> = ct.chars().collect();
        let last = chars.len() - 1;
        chars[last] = if chars[last] == '0' { '1' } else { '0' };
        t.envelope["ct"] = json!(chars.into_iter().collect::<String>());
        assert!(unwrap(&t).is_err());

        // Tamper the ephemeral / recipient pubkey, epoch, org, publisher label —
        // every one is under the signature, so each fails verify.
        let mut t = base.clone();
        t.ephemeral_pub = to_hex(bob_pub.as_bytes());
        assert!(unwrap(&t).is_err());
        let mut t = base.clone();
        t.recipient_pub = to_hex(bob_pub.as_bytes());
        assert!(unwrap(&t).is_err());
        let mut t = base.clone();
        t.epoch = 2;
        assert!(unwrap(&t).is_err());
        let mut t = base.clone();
        t.org = "evil".into();
        assert!(unwrap(&t).is_err());
        let mut t = base.clone();
        t.publisher = "acc_mallory".into();
        assert!(unwrap(&t).is_err());

        // Tamper the signature itself.
        let mut t = base.clone();
        let mut sig: Vec<char> = t.signature.chars().collect();
        sig[0] = if sig[0] == '0' { '1' } else { '0' };
        t.signature = sig.into_iter().collect();
        assert!(unwrap(&t).is_err());
    }

    #[test]
    fn identities_are_deterministic_and_domain_separated() {
        // Same login+user → same X25519 AND same Ed25519 key; the two are derived
        // under DISTINCT HKDF domains, so neither reveals the other.
        let a = x25519_id(b"same-login", "acc_x");
        let b = x25519_id(b"same-login", "acc_x");
        assert_eq!(x25519_public(&a).as_bytes(), x25519_public(&b).as_bytes());
        let s1 = ed25519_id(b"same-login", "acc_x");
        let s2 = ed25519_id(b"same-login", "acc_x");
        assert_eq!(
            ed25519_verifying(&s1).to_bytes(),
            ed25519_verifying(&s2).to_bytes()
        );
        // Different user / different login → different keys, both curves.
        assert_ne!(
            x25519_public(&a).as_bytes(),
            x25519_public(&x25519_id(b"same-login", "acc_y")).as_bytes()
        );
        assert_ne!(
            ed25519_verifying(&s1).to_bytes(),
            ed25519_verifying(&ed25519_id(b"other-login", "acc_x")).to_bytes()
        );
        // The X25519 and Ed25519 32-byte public encodings must not coincide.
        assert_ne!(
            x25519_public(&a).as_bytes(),
            &ed25519_verifying(&s1).to_bytes()
        );
    }

    #[test]
    fn argon2id_stretch_is_deterministic_and_domain_separated() {
        // Cross-device determinism: same passphrase + user → same stretched master
        // → same published identity keys (the property the whole scheme rests on).
        let a = StretchedMaster::from_passphrase(b"correct horse battery staple", "acc_u1");
        let b = StretchedMaster::from_passphrase(b"correct horse battery staple", "acc_u1");
        assert_eq!(a.profile(), KdfProfile::Argon2idV1);
        assert_eq!(
            x25519_public(&derive_x25519_identity(&a, "acc_u1")).as_bytes(),
            x25519_public(&derive_x25519_identity(&b, "acc_u1")).as_bytes(),
            "same passphrase+user must derive the same identity on every device"
        );
        // Different passphrase OR different user → different keys (salt + info).
        let diff_pass = StretchedMaster::from_passphrase(b"hunter2", "acc_u1");
        assert_ne!(
            x25519_public(&derive_x25519_identity(&a, "acc_u1")).as_bytes(),
            x25519_public(&derive_x25519_identity(&diff_pass, "acc_u1")).as_bytes()
        );
        let diff_user = StretchedMaster::from_passphrase(b"correct horse battery staple", "acc_u2");
        assert_ne!(
            x25519_public(&derive_x25519_identity(&a, "acc_u1")).as_bytes(),
            x25519_public(&derive_x25519_identity(&diff_user, "acc_u2")).as_bytes(),
            "the per-user Argon2id salt + HKDF info domain-separate users"
        );
        // The issued-high-entropy path carries a distinct profile and (being a
        // different derivation) yields different keys than the Argon2id path.
        let issued =
            StretchedMaster::from_issued_high_entropy(b"correct horse battery staple", "acc_u1");
        assert_eq!(issued.profile(), KdfProfile::IssuedHkdfV1);
        assert_ne!(
            x25519_public(&derive_x25519_identity(&a, "acc_u1")).as_bytes(),
            x25519_public(&derive_x25519_identity(&issued, "acc_u1")).as_bytes()
        );
    }

    #[test]
    fn wrap_rejects_low_order_recipient_key() {
        // The all-zero X25519 point is low-order → non-contributory DH.
        let low_order = PublicKey::from([0u8; 32]);
        assert!(wrap_org_key(
            &[1u8; 32],
            "acme",
            1,
            "acc_x",
            &low_order,
            "acc_granter",
            &granter()
        )
        .is_err());
    }

    #[test]
    fn non_canonical_org_is_rejected_on_wrap_and_unwrap() {
        let alice = x25519_id(b"alice", "acc_alice");
        // Wrap refuses a non-slug org (Unicode / delimiter / space).
        for bad in ["Acme corp", "org/evil", "acmé", ""] {
            assert!(
                wrap_org_key(
                    &[1u8; 32],
                    bad,
                    1,
                    "acc_alice",
                    &x25519_public(&alice),
                    "acc_granter",
                    &granter()
                )
                .is_err(),
                "wrap must reject non-canonical org {bad:?}"
            );
        }
        // A blob whose org is mutated after signing is refused. ("Acme" is itself
        // a valid slug — uppercase is allowed — so this is caught by the SIGNATURE
        // layer, not require_canonical_org: the transcript diverges. Upstream the
        // platform must mint ONE canonical org id so "Acme"/"acme" never coexist.)
        let mut t = wrap_by_granter(&[1u8; 32], "acme", 1, "acc_alice", &x25519_public(&alice));
        t.org = "Acme".into();
        assert!(unwrap_org_key(&t, &alice, "acc_alice", &trusted()).is_err());
    }

    #[test]
    fn org_wrap_info_is_injective_under_delimiter_injection() {
        let e = x25519_public(&x25519_id(b"e", "e"));
        let p = x25519_public(&x25519_id(b"p", "p"));
        // These two (org, recipient) tuples collide under naive `/`+`:`
        // interpolation; length-prefixing must keep the transcript distinct.
        let a = org_wrap_info("acme/epoch:1/recipient:mallory", 1, "acc_alice", &e, &p);
        let b = org_wrap_info("acme", 1, "mallory/epoch:1/recipient:acc_alice", &e, &p);
        assert_ne!(a, b, "delimiter injection must not collide the transcript");
    }

    #[test]
    fn all_members_derive_the_same_org_audience_key() {
        // The whole point: with a SHARED k_org, every member derives the SAME
        // org-audience AEAD key — closing the gap the old per-user derivation
        // left (where each member got a different, non-interoperable org key).
        let alice = x25519_id(b"alice", "acc_alice");
        let bob = x25519_id(b"bob", "acc_bob");
        let k_org = [42u8; 32];
        let ka = unwrap_org_key(
            &wrap_by_granter(&k_org, "acme", 1, "acc_alice", &x25519_public(&alice)),
            &alice,
            "acc_alice",
            &trusted(),
        )
        .unwrap();
        let kb = unwrap_org_key(
            &wrap_by_granter(&k_org, "acme", 1, "acc_bob", &x25519_public(&bob)),
            &bob,
            "acc_bob",
            &trusted(),
        )
        .unwrap();
        assert_eq!(ka, kb);
        assert_eq!(
            derive_key(&ka, "org:acme/epoch:1"),
            derive_key(&kb, "org:acme/epoch:1")
        );
    }
}

#[cfg(test)]
mod tests {
    use super::*;
    use crate::oplog::{logical_clock, verify_log, DeviceLog, Surface};
    use serde_json::json;

    #[test]
    fn personal_envelope_omits_kid_on_the_wire() {
        // LOAD-BEARING: personal (LocalKeyCipher) envelopes must serialize WITHOUT a
        // `kid` field, byte-identical to pre-org-scope envelopes. `wrap_org_key`
        // signs `canonical_json(envelope)`, so a stray always-null `kid` would break
        // every existing wrap signature. This pins `skip_serializing_if`.
        let cipher = LocalKeyCipher::generate();
        let env = cipher.encrypt(&json!({"x": 1})).unwrap();
        let obj = env.as_object().unwrap();
        assert!(!obj.contains_key("kid"), "personal envelope must omit kid");
        assert_eq!(
            obj.keys()
                .cloned()
                .collect::<std::collections::BTreeSet<_>>(),
            ["car_enc", "ct", "nonce"]
                .into_iter()
                .map(String::from)
                .collect::<std::collections::BTreeSet<_>>(),
            "exactly the legacy three fields"
        );
    }

    #[test]
    fn multi_epoch_org_cipher_selects_by_kid_and_fails_closed() {
        // Two epochs held. Encrypt uses the NEWEST; each envelope carries its kid;
        // decrypt selects EXACTLY that epoch's key — never trial-decrypts. An
        // envelope whose kid we don't hold fails closed.
        let mut keys = std::collections::BTreeMap::new();
        keys.insert(1u64, Zeroizing::new([1u8; 32]));
        keys.insert(2u64, Zeroizing::new([2u8; 32]));
        let cipher = MultiEpochOrgCipher::new("org:acme", keys);

        let msg = json!({"shared": "brain"});
        let env = cipher.encrypt(&msg).unwrap();
        assert_eq!(
            env.get("kid").and_then(|v| v.as_u64()),
            Some(2),
            "encrypts under the newest epoch"
        );
        assert_eq!(cipher.decrypt(&env).unwrap(), msg);

        // Only epoch 1 held → an op stamped kid=2 is opaque (fail closed).
        let mut only1 = std::collections::BTreeMap::new();
        only1.insert(1u64, Zeroizing::new([1u8; 32]));
        let e1 = MultiEpochOrgCipher::new("org:acme", only1);
        assert!(matches!(e1.decrypt(&env), Err(CryptoError::Key(_))));
    }

    #[test]
    fn org_cipher_aad_binds_epoch_and_audience() {
        // The AAD binds (algorithm, audience, kid). Tampering the kid on the wire, or
        // replaying the ciphertext under a cipher for a DIFFERENT audience, both fail
        // the AEAD open — never a silent wrong-context accept.
        let mut keys = std::collections::BTreeMap::new();
        keys.insert(5u64, Zeroizing::new([5u8; 32]));
        let acme = MultiEpochOrgCipher::new("org:acme", keys.clone());
        let env = acme.encrypt(&json!({"m": 1})).unwrap();

        // Same key bytes, different audience string → AAD differs → Decrypt error.
        let globex = MultiEpochOrgCipher::new("org:globex", keys);
        assert!(matches!(globex.decrypt(&env), Err(CryptoError::Decrypt)));

        // Flip the kid to an epoch we DO hold but that wasn't used → AAD mismatch.
        let mut two = std::collections::BTreeMap::new();
        two.insert(5u64, Zeroizing::new([5u8; 32]));
        two.insert(6u64, Zeroizing::new([5u8; 32])); // same bytes, different epoch
        let acme2 = MultiEpochOrgCipher::new("org:acme", two);
        let mut tampered = env.clone();
        tampered["kid"] = json!(6);
        assert!(matches!(
            acme2.decrypt(&tampered),
            Err(CryptoError::Decrypt)
        ));
    }

    #[test]
    fn local_key_cipher_round_trips() {
        let cipher = LocalKeyCipher::generate();
        let plaintext = json!({"id": "f1", "secret": "the launch codes", "n": 42});
        let env = cipher.encrypt(&plaintext).unwrap();
        assert!(Envelope::is_envelope(&env));
        assert_eq!(cipher.decrypt(&env).unwrap(), plaintext);

        // Randomized nonce: two encryptions of the same plaintext differ.
        let env2 = cipher.encrypt(&plaintext).unwrap();
        assert_ne!(env, env2, "each encryption uses a fresh nonce");
        assert_eq!(cipher.decrypt(&env2).unwrap(), plaintext);
    }

    #[test]
    fn encrypted_op_chain_verifies_and_relay_sees_only_ciphertext() {
        // A device authors two ops with ENCRYPTED payloads. The op_id chain is
        // ciphertext-native, so verify_log passes and the relay (which only
        // ever holds op.payload) sees no plaintext — exactly the proposal's
        // "the relay stores only ciphertext; op_id/hlc stay cleartext".
        let cipher = LocalKeyCipher::generate();
        let mut dev = DeviceLog::new("mac-a");
        dev.set_wall_clock(logical_clock());

        let secret1 = json!({"id": "f1", "body": "the sky is blue"});
        let secret2 = json!({"id": "f2", "body": "water is wet"});
        let op1 = dev.append(
            Scope::Personal,
            Surface::Knowledge,
            cipher.encrypt(&secret1).unwrap(),
        );
        let op2 = dev.append(
            Scope::Personal,
            Surface::Knowledge,
            cipher.encrypt(&secret2).unwrap(),
        );

        // The ciphertext chain verifies (op_id covers the ciphertext payload).
        verify_log(&[op1.clone(), op2.clone()]).unwrap();
        assert!(op1.id_valid());

        // The wire form leaks nothing: no "body"/"id" fields, only the envelope.
        for op in [&op1, &op2] {
            assert!(Envelope::is_envelope(&op.payload));
            assert!(op.payload.get("body").is_none());
            assert!(op.payload.get("id").is_none());
        }

        // A peer holding the key recovers the plaintext.
        assert_eq!(cipher.decrypt(&op1.payload).unwrap(), secret1);
        assert_eq!(cipher.decrypt(&op2.payload).unwrap(), secret2);
    }

    #[test]
    fn tampered_ciphertext_is_rejected() {
        let cipher = LocalKeyCipher::generate();
        let env = cipher.encrypt(&json!({"x": 1})).unwrap();

        // Flip one hex nibble of the ciphertext → AEAD tag mismatch → refusal.
        let mut tampered = env.clone();
        let ct = tampered["ct"].as_str().unwrap().to_string();
        let flipped: String = {
            let mut chars: Vec<char> = ct.chars().collect();
            chars[0] = if chars[0] == '0' { '1' } else { '0' };
            chars.into_iter().collect()
        };
        tampered["ct"] = json!(flipped);
        assert!(matches!(
            cipher.decrypt(&tampered),
            Err(CryptoError::Decrypt)
        ));
    }

    #[test]
    fn wrong_key_cannot_decrypt() {
        let cipher = LocalKeyCipher::generate();
        let other = LocalKeyCipher::generate();
        let env = cipher.encrypt(&json!({"x": 1})).unwrap();
        assert!(matches!(other.decrypt(&env), Err(CryptoError::Decrypt)));
    }

    #[test]
    fn load_or_generate_persists_and_reloads_the_same_key() {
        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("sync").join("personal.key");
        let a = LocalKeyCipher::load_or_generate(&path).unwrap();
        assert!(path.exists());
        let b = LocalKeyCipher::load_or_generate(&path).unwrap();
        assert_eq!(
            a.key_hex(),
            b.key_hex(),
            "the persisted key reloads identically"
        );

        // And the reloaded key decrypts the first cipher's output (same key).
        let env = a.encrypt(&json!({"k": "v"})).unwrap();
        assert_eq!(b.decrypt(&env).unwrap(), json!({"k": "v"}));
    }

    #[test]
    fn scope_maps_to_a_single_encryption_audience() {
        assert_eq!(encryption_audience(&Scope::Personal), "personal");
        assert_eq!(
            encryption_audience(&Scope::Shared { org: "acme".into() }),
            "org:acme"
        );
    }

    #[test]
    fn same_login_master_derives_interoperable_keys_across_devices() {
        // Mac and phone each build a provider from the SAME login master. A
        // payload the Mac encrypts under `Personal` must decrypt on the phone —
        // the whole "my devices share config after one login" property.
        let master = b"parslee-issued-per-user-sync-secret";
        let mac = DerivedKeyProvider::new(master.to_vec());
        let phone = DerivedKeyProvider::new(master.to_vec());

        let secret = json!({"messaging_allowlist": ["+15551234567"]});
        let env = mac.cipher_for(&Scope::Personal).encrypt(&secret).unwrap();
        assert_eq!(
            phone.cipher_for(&Scope::Personal).decrypt(&env).unwrap(),
            secret
        );
    }

    #[test]
    fn personal_and_org_audiences_are_cryptographically_isolated() {
        let p = DerivedKeyProvider::new(b"master".to_vec());
        let env = p
            .cipher_for(&Scope::Personal)
            .encrypt(&json!({"x": 1}))
            .unwrap();
        // The org key cannot read a personal-audience ciphertext.
        assert!(matches!(
            p.cipher_for(&Scope::Shared { org: "acme".into() })
                .decrypt(&env),
            Err(CryptoError::Decrypt)
        ));
    }

    #[test]
    fn passphrase_derives_the_same_keys_on_every_device_zero_knowledge() {
        // The zero-knowledge path: same passphrase + user → same keys, so the
        // phone reads what the Mac wrote, with no server ever holding the key.
        let mac = DerivedKeyProvider::from_passphrase("correct horse battery staple", "user-1");
        let phone = DerivedKeyProvider::from_passphrase("correct horse battery staple", "user-1");
        let env = mac
            .cipher_for(&Scope::Personal)
            .encrypt(&json!({"s": 1}))
            .unwrap();
        assert_eq!(
            phone.cipher_for(&Scope::Personal).decrypt(&env).unwrap(),
            json!({"s": 1})
        );
        // A wrong passphrase cannot read it.
        let wrong = DerivedKeyProvider::from_passphrase("hunter2", "user-1");
        assert!(matches!(
            wrong.cipher_for(&Scope::Personal).decrypt(&env),
            Err(CryptoError::Decrypt)
        ));
    }

    #[test]
    fn a_different_login_cannot_decrypt() {
        let mine = DerivedKeyProvider::new(b"my-secret".to_vec());
        let theirs = DerivedKeyProvider::new(b"their-secret".to_vec());
        let env = mine
            .cipher_for(&Scope::Personal)
            .encrypt(&json!({"x": 1}))
            .unwrap();
        assert!(matches!(
            theirs.cipher_for(&Scope::Personal).decrypt(&env),
            Err(CryptoError::Decrypt)
        ));
    }

    #[test]
    fn from_login_secret_is_stable_per_user_and_distinct_across_users() {
        let raw = b"raw-oauth-derived-material";
        // Two sign-ins for the same user → same keys (idempotent onboarding).
        let a = DerivedKeyProvider::from_login_secret(raw, "user-1");
        let b = DerivedKeyProvider::from_login_secret(raw, "user-1");
        let env = a
            .cipher_for(&Scope::Personal)
            .encrypt(&json!({"k": "v"}))
            .unwrap();
        assert_eq!(
            b.cipher_for(&Scope::Personal).decrypt(&env).unwrap(),
            json!({"k": "v"})
        );
        // A different user derives a different master → cannot decrypt.
        let other = DerivedKeyProvider::from_login_secret(raw, "user-2");
        assert!(matches!(
            other.cipher_for(&Scope::Personal).decrypt(&env),
            Err(CryptoError::Decrypt)
        ));
    }
}