use crate::auth::now_secs;
use crate::config::{ServerConfig, expand_tilde};
use crate::crypto;
use anyhow::{Context, Result, bail};
use base64::Engine;
use base64::engine::general_purpose::{STANDARD, URL_SAFE_NO_PAD};
use ed25519_dalek::{Signature, Signer, SigningKey, Verifier, VerifyingKey};
use rsa::traits::PublicKeyParts;
use serde::{Deserialize, Serialize};
use signature::{SignatureEncoding, Signer as SignatureSigner, Verifier as SignatureVerifier};
use std::fs;
use std::io::Write;
use std::net::IpAddr;
#[cfg(unix)]
use std::os::unix::fs::OpenOptionsExt;
use std::path::Path;
use std::str::FromStr;
use x25519_dalek::{PublicKey as X25519PublicKey, StaticSecret};

pub const HOST_KEY_ALGORITHM: &str = "dosh-ed25519";
pub const NATIVE_PROTOCOL_VERSION: u8 = 2;

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct HostPublicKey {
    pub algorithm: String,
    pub key: [u8; 32],
}

#[derive(Debug, Clone, PartialEq, Eq)]
pub struct KnownHost {
    pub host: String,
    pub algorithm: String,
    pub key: [u8; 32],
    pub first_seen: u64,
    pub source: String,
}

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct NativeClientHello {
    pub protocol_version: u8,
    pub client_random: [u8; 32],
    pub client_ephemeral_public: [u8; 32],
    pub requested_host: String,
    pub requested_user: String,
    pub requested_session: String,
    pub requested_mode: String,
    pub terminal_size: (u16, u16),
    pub supported_aead: Vec<String>,
    pub supported_user_key_algorithms: Vec<String>,
    pub cached_host_key_fingerprint: Option<String>,
    pub attach_ticket_envelope: Option<Vec<u8>>,
    #[serde(default)]
    pub requested_env: Vec<EnvVar>,
}

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct EnvVar {
    pub name: String,
    pub value: String,
}

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct NativeServerHello {
    pub protocol_version: u8,
    pub server_random: [u8; 32],
    pub server_ephemeral_public: [u8; 32],
    pub host_key: HostPublicKey,
    pub chosen_aead: String,
    pub server_key_epoch: u64,
    pub auth_challenge: [u8; 32],
    pub rate_limit_remaining: Option<u32>,
    pub host_signature: Vec<u8>,
}

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct NativeUserAuth {
    pub public_key_algorithm: String,
    pub public_key: Vec<u8>,
    pub signature: Vec<u8>,
    pub requested_forwardings: Vec<ForwardingRequest>,
}

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct ForwardingRequest {
    pub kind: ForwardingKind,
    pub bind_host: Option<String>,
    pub listen_port: u16,
    pub target_host: Option<String>,
    pub target_port: Option<u16>,
}

#[derive(Debug, Clone, Copy, PartialEq, Eq, Serialize, Deserialize)]
pub enum ForwardingKind {
    Local,
    Remote,
    Dynamic,
    /// SSH-agent forwarding: the client opts in and, if the server policy allows
    /// (`allow_agent_forwarding`), the server exports a proxy unix socket as
    /// `SSH_AUTH_SOCK` in the remote session and tunnels each connection back to
    /// the client's local agent over a Dosh stream. Added at the end of the enum
    /// so bincode discriminants for the existing variants are unchanged.
    Agent,
}

#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
pub struct NativeAuthOk {
    pub client_id: [u8; 16],
    pub session: String,
    pub mode: String,
    pub session_key: [u8; 32],
    pub session_key_id: [u8; 16],
    pub attach_ticket: Vec<u8>,
    pub attach_ticket_psk: [u8; 32],
    pub initial_seq: u64,
    pub snapshot: Vec<u8>,
    pub policy_flags: Vec<String>,
}

#[derive(Debug, Clone, PartialEq, Eq)]
pub struct AuthorizedKey {
    pub algorithm: String,
    pub key: Vec<u8>,
    pub options: AuthorizedKeyOptions,
    pub comment: Option<String>,
}

#[derive(Debug, Clone, Default, PartialEq, Eq)]
pub struct AuthorizedKeyOptions {
    pub from: Option<String>,
    pub force_command: Option<String>,
    pub restricted: bool,
    pub no_port_forwarding: bool,
    pub permitopen: Vec<String>,
    pub unsupported: Vec<String>,
}

pub fn load_or_create_host_key(config: &ServerConfig) -> Result<SigningKey> {
    let path = expand_tilde(&config.host_key);
    if path.exists() {
        let raw = fs::read(&path).with_context(|| format!("read {}", path.display()))?;
        let decoded = if raw.len() == 32 {
            raw
        } else {
            URL_SAFE_NO_PAD
                .decode(String::from_utf8_lossy(&raw).trim())
                .context("decode Dosh host key")?
        };
        anyhow::ensure!(decoded.len() == 32, "Dosh host key must be 32 bytes");
        let mut bytes = [0u8; 32];
        bytes.copy_from_slice(&decoded);
        return Ok(SigningKey::from_bytes(&bytes));
    }
    if let Some(parent) = path.parent() {
        fs::create_dir_all(parent).with_context(|| format!("create {}", parent.display()))?;
    }
    let bytes = crypto::random_32();
    let mut options = fs::OpenOptions::new();
    options.create_new(true).write(true);
    #[cfg(unix)]
    options.mode(0o600);
    let mut file = options
        .open(&path)
        .with_context(|| format!("create {}", path.display()))?;
    file.write_all(URL_SAFE_NO_PAD.encode(bytes).as_bytes())?;
    file.write_all(b"\n")?;
    Ok(SigningKey::from_bytes(&bytes))
}

pub fn host_public_key(signing_key: &SigningKey) -> HostPublicKey {
    let verifying = VerifyingKey::from(signing_key);
    HostPublicKey {
        algorithm: HOST_KEY_ALGORITHM.to_string(),
        key: verifying.to_bytes(),
    }
}

pub fn host_public_key_line(key: &HostPublicKey) -> String {
    format!(
        "{} {} {}",
        key.algorithm,
        URL_SAFE_NO_PAD.encode(key.key),
        host_fingerprint(key)
    )
}

pub fn parse_host_public_key_line(raw: &str) -> Result<HostPublicKey> {
    let mut parts = raw.split_whitespace();
    let algorithm = parts.next().context("missing Dosh host key algorithm")?;
    if algorithm != HOST_KEY_ALGORITHM {
        bail!("unsupported Dosh host key algorithm {algorithm}");
    }
    let key_raw = parts.next().context("missing Dosh host public key")?;
    let decoded = URL_SAFE_NO_PAD
        .decode(key_raw)
        .context("decode Dosh host public key")?;
    anyhow::ensure!(decoded.len() == 32, "Dosh host public key must be 32 bytes");
    let mut key = [0u8; 32];
    key.copy_from_slice(&decoded);
    Ok(HostPublicKey {
        algorithm: algorithm.to_string(),
        key,
    })
}

pub fn host_fingerprint(key: &HostPublicKey) -> String {
    format!(
        "SHA256:{}",
        URL_SAFE_NO_PAD.encode(crypto::sha256(&key.key))
    )
}

pub fn sign_host_transcript(signing_key: &SigningKey, transcript: &[u8]) -> [u8; 64] {
    signing_key.sign(transcript).to_bytes()
}

pub fn verify_host_signature(
    host_key: &HostPublicKey,
    transcript: &[u8],
    signature: &[u8],
) -> Result<()> {
    if host_key.algorithm != HOST_KEY_ALGORITHM {
        bail!("unsupported Dosh host key algorithm {}", host_key.algorithm);
    }
    let verifying_key =
        VerifyingKey::from_bytes(&host_key.key).context("parse Dosh host verifying key")?;
    anyhow::ensure!(
        signature.len() == 64,
        "Dosh host signature must be 64 bytes"
    );
    let mut signature_bytes = [0u8; 64];
    signature_bytes.copy_from_slice(signature);
    let signature = Signature::from_bytes(&signature_bytes);
    verifying_key
        .verify(transcript, &signature)
        .context("verify Dosh host signature")
}

pub fn server_hello_transcript(
    client: &NativeClientHello,
    server: &NativeServerHello,
) -> Result<Vec<u8>> {
    let mut unsigned = server.clone();
    unsigned.host_signature.clear();
    let mut out = b"dosh/native/server-hello/v1".to_vec();
    out.extend(bincode::serialize(client)?);
    out.extend(bincode::serialize(&unsigned)?);
    Ok(out)
}

pub fn sign_server_hello(
    signing_key: &SigningKey,
    client: &NativeClientHello,
    server: &mut NativeServerHello,
) -> Result<()> {
    server.host_signature.clear();
    let transcript = server_hello_transcript(client, server)?;
    server.host_signature = sign_host_transcript(signing_key, &transcript).to_vec();
    Ok(())
}

/// Error raised when a native handshake peer speaks a different protocol version.
///
/// Carries the peer's advertised version so callers can render an actionable,
/// named message ("upgrade dosh") rather than letting a mismatch surface as an
/// opaque decrypt failure or a silent timeout. The `Display` text deliberately
/// embeds [`crate::protocol::VERSION_MISMATCH_REASON`] so the server's reject and
/// the client's local error read the same way.
#[derive(Debug, Clone, Copy, PartialEq, Eq)]
pub struct ProtocolVersionMismatch {
    pub local: u8,
    pub remote: u8,
    pub peer: &'static str,
}

impl std::fmt::Display for ProtocolVersionMismatch {
    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
        write!(
            f,
            "{} ({} speaks native protocol v{}, this build speaks v{})",
            crate::protocol::VERSION_MISMATCH_REASON,
            self.peer,
            self.remote,
            self.local,
        )
    }
}

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

/// Verify a peer-advertised native protocol version against this build.
///
/// `peer` names whose version was wrong ("client" or "server") for the error
/// message. Returns a typed [`ProtocolVersionMismatch`] so the caller can both
/// match on it and print an actionable, upgrade-oriented message.
pub fn check_native_protocol_version(version: u8, peer: &'static str) -> Result<()> {
    if version != NATIVE_PROTOCOL_VERSION {
        return Err(ProtocolVersionMismatch {
            local: NATIVE_PROTOCOL_VERSION,
            remote: version,
            peer,
        }
        .into());
    }
    Ok(())
}

pub fn verify_server_hello(client: &NativeClientHello, server: &NativeServerHello) -> Result<()> {
    check_native_protocol_version(client.protocol_version, "client")?;
    check_native_protocol_version(server.protocol_version, "server")?;
    let transcript = server_hello_transcript(client, server)?;
    verify_host_signature(&server.host_key, &transcript, &server.host_signature)
}

pub fn user_auth_transcript(
    client: &NativeClientHello,
    server: &NativeServerHello,
    auth: &NativeUserAuth,
) -> Result<Vec<u8>> {
    let mut unsigned = auth.clone();
    unsigned.signature.clear();
    let mut out = b"dosh/native/user-auth/v1".to_vec();
    out.extend(bincode::serialize(client)?);
    out.extend(bincode::serialize(server)?);
    out.extend(bincode::serialize(&unsigned)?);
    Ok(out)
}

pub fn sign_user_auth(
    signing_key: &SigningKey,
    client: &NativeClientHello,
    server: &NativeServerHello,
    requested_forwardings: Vec<ForwardingRequest>,
) -> Result<NativeUserAuth> {
    let verifying = VerifyingKey::from(signing_key);
    let mut auth = NativeUserAuth {
        public_key_algorithm: "ssh-ed25519".to_string(),
        public_key: verifying.to_bytes().to_vec(),
        signature: Vec::new(),
        requested_forwardings,
    };
    let transcript = user_auth_transcript(client, server, &auth)?;
    auth.signature = signing_key.sign(&transcript).to_bytes().to_vec();
    Ok(auth)
}

pub fn sign_user_auth_with_private_key(
    private_key: &ssh_key::PrivateKey,
    client: &NativeClientHello,
    server: &NativeServerHello,
    requested_forwardings: Vec<ForwardingRequest>,
) -> Result<NativeUserAuth> {
    anyhow::ensure!(!private_key.is_encrypted(), "OpenSSH identity is encrypted");
    let public_key = private_key.public_key();
    let key_algorithm = public_key.algorithm().as_str().to_string();
    anyhow::ensure!(
        is_supported_user_key_algorithm(&key_algorithm),
        "unsupported native identity key algorithm {key_algorithm}"
    );
    let public_key_blob = ssh_public_blob_from_public_key(public_key)?;
    let public_key_for_auth = if key_algorithm == "ssh-ed25519" {
        parse_ssh_ed25519_public_blob(&public_key_blob)?.to_vec()
    } else {
        public_key_blob
    };
    let signature_algorithm = signature_algorithm_for_private_key(&key_algorithm)?;
    let mut auth = NativeUserAuth {
        public_key_algorithm: signature_algorithm.to_string(),
        public_key: public_key_for_auth,
        signature: Vec::new(),
        requested_forwardings,
    };
    let transcript = user_auth_transcript(client, server, &auth)?;
    auth.signature = if key_algorithm == "ssh-rsa" {
        sign_rsa_sha512_private_key(private_key, &transcript)?
    } else {
        let signature = SignatureSigner::try_sign(private_key, &transcript)
            .context("sign native user auth with OpenSSH private key")?;
        anyhow::ensure!(
            signature.algorithm().as_str() == auth.public_key_algorithm,
            "private key produced signature algorithm {}, expected {}",
            signature.algorithm().as_str(),
            auth.public_key_algorithm
        );
        signature.as_bytes().to_vec()
    };
    Ok(auth)
}

fn sign_rsa_sha512_private_key(
    private_key: &ssh_key::PrivateKey,
    transcript: &[u8],
) -> Result<Vec<u8>> {
    let rsa_keypair = private_key
        .key_data()
        .rsa()
        .ok_or_else(|| anyhow::anyhow!("OpenSSH identity is not ssh-rsa"))?;
    let rsa_private = rsa_private_key_from_ssh_keypair(rsa_keypair)?;
    let signing_key = rsa::pkcs1v15::SigningKey::<sha2::Sha512>::new(rsa_private);
    let signature: rsa::pkcs1v15::Signature = SignatureSigner::sign(&signing_key, transcript);
    Ok(signature.to_vec())
}

fn rsa_private_key_from_ssh_keypair(
    keypair: &ssh_key::private::RsaKeypair,
) -> Result<rsa::RsaPrivateKey> {
    let private = rsa::RsaPrivateKey::from_components(
        rsa::BigUint::try_from(&keypair.public.n).context("convert RSA modulus")?,
        rsa::BigUint::try_from(&keypair.public.e).context("convert RSA public exponent")?,
        rsa::BigUint::try_from(&keypair.private.d).context("convert RSA private exponent")?,
        vec![
            rsa::BigUint::try_from(&keypair.private.p).context("convert RSA p prime")?,
            rsa::BigUint::try_from(&keypair.private.q).context("convert RSA q prime")?,
        ],
    )
    .context("convert OpenSSH RSA private key")?;
    anyhow::ensure!(
        private.size().saturating_mul(8) >= 2048,
        "OpenSSH RSA identity is smaller than 2048 bits"
    );
    Ok(private)
}

fn signature_algorithm_for_private_key(key_algorithm: &str) -> Result<&'static str> {
    match key_algorithm {
        "ssh-ed25519" => Ok("ssh-ed25519"),
        "ecdsa-sha2-nistp256" => Ok("ecdsa-sha2-nistp256"),
        "ssh-rsa" => Ok("rsa-sha2-512"),
        _ => bail!("unsupported native identity key algorithm {key_algorithm}"),
    }
}

pub fn verify_native_user_auth(
    client: &NativeClientHello,
    server: &NativeServerHello,
    auth: &NativeUserAuth,
    authorized_keys: &[AuthorizedKey],
    source_ip: Option<IpAddr>,
) -> Result<AuthorizedKey> {
    anyhow::ensure!(
        is_supported_user_signature_algorithm(&auth.public_key_algorithm),
        "unsupported native user key algorithm {}",
        auth.public_key_algorithm
    );
    let authorized_algorithm = authorized_key_algorithm_for_auth(&auth.public_key_algorithm)?;
    let authorized = authorized_keys
        .iter()
        .find(|key| key.algorithm == authorized_algorithm && key.key == auth.public_key)
        .ok_or_else(|| anyhow::anyhow!("native user key is not authorized"))?;
    authorized.ensure_native_allowed(auth, source_ip)?;

    let transcript = user_auth_transcript(client, server, auth)?;
    verify_native_user_signature(auth, &transcript)?;
    Ok(authorized.clone())
}

pub fn supported_user_key_algorithms() -> Vec<String> {
    vec![
        "ssh-ed25519".to_string(),
        "ecdsa-sha2-nistp256".to_string(),
        "rsa-sha2-512".to_string(),
        "rsa-sha2-256".to_string(),
    ]
}

pub fn is_supported_user_key_algorithm(algorithm: &str) -> bool {
    matches!(algorithm, "ssh-ed25519" | "ecdsa-sha2-nistp256" | "ssh-rsa")
}

pub fn is_supported_user_signature_algorithm(algorithm: &str) -> bool {
    matches!(
        algorithm,
        "ssh-ed25519" | "ecdsa-sha2-nistp256" | "rsa-sha2-512" | "rsa-sha2-256"
    )
}

fn authorized_key_algorithm_for_auth(signature_algorithm: &str) -> Result<&'static str> {
    match signature_algorithm {
        "ssh-ed25519" => Ok("ssh-ed25519"),
        "ecdsa-sha2-nistp256" => Ok("ecdsa-sha2-nistp256"),
        "rsa-sha2-512" | "rsa-sha2-256" => Ok("ssh-rsa"),
        _ => bail!("unsupported native user key algorithm {signature_algorithm}"),
    }
}

fn verify_native_user_signature(auth: &NativeUserAuth, transcript: &[u8]) -> Result<()> {
    match auth.public_key_algorithm.as_str() {
        "ssh-ed25519" => {
            anyhow::ensure!(
                auth.public_key.len() == 32,
                "ssh-ed25519 public key must be 32 bytes"
            );
            anyhow::ensure!(
                auth.signature.len() == 64,
                "ssh-ed25519 signature must be 64 bytes"
            );
            let mut public_key = [0u8; 32];
            public_key.copy_from_slice(&auth.public_key);
            let verifying_key =
                VerifyingKey::from_bytes(&public_key).context("parse user public key")?;
            let mut signature = [0u8; 64];
            signature.copy_from_slice(&auth.signature);
            let signature = Signature::from_bytes(&signature);
            verifying_key
                .verify(transcript, &signature)
                .context("verify native user signature")?;
        }
        "ecdsa-sha2-nistp256" => {
            let public_key = ssh_public_key_from_blob(&auth.public_key)
                .context("parse native user SSH public key")?;
            let algorithm =
                ssh_key::Algorithm::from_str(&auth.public_key_algorithm).with_context(|| {
                    format!("parse signature algorithm {}", auth.public_key_algorithm)
                })?;
            let signature = ssh_key::Signature::new(algorithm, auth.signature.clone())
                .context("parse native user SSH signature")?;
            SignatureVerifier::verify(public_key.key_data(), transcript, &signature)
                .context("verify native user SSH signature")?;
        }
        "rsa-sha2-512" | "rsa-sha2-256" => {
            verify_rsa_sha2_signature(
                &auth.public_key,
                &auth.public_key_algorithm,
                transcript,
                &auth.signature,
            )?;
        }
        algorithm => bail!("unsupported native user key algorithm {algorithm}"),
    }
    Ok(())
}

fn verify_rsa_sha2_signature(
    public_key_blob: &[u8],
    signature_algorithm: &str,
    transcript: &[u8],
    signature: &[u8],
) -> Result<()> {
    let (e, n) = parse_ssh_rsa_public_blob(public_key_blob)?;
    let public = rsa::RsaPublicKey::new(
        rsa::BigUint::from_bytes_be(n),
        rsa::BigUint::from_bytes_be(e),
    )
    .context("parse RSA public key")?;
    let signature =
        rsa::pkcs1v15::Signature::try_from(signature).context("parse RSA PKCS#1v1.5 signature")?;
    match signature_algorithm {
        "rsa-sha2-256" => {
            let key = rsa::pkcs1v15::VerifyingKey::<sha2::Sha256>::new(public);
            SignatureVerifier::verify(&key, transcript, &signature)
                .context("verify RSA-SHA256 signature")
        }
        "rsa-sha2-512" => {
            let key = rsa::pkcs1v15::VerifyingKey::<sha2::Sha512>::new(public);
            SignatureVerifier::verify(&key, transcript, &signature)
                .context("verify RSA-SHA512 signature")
        }
        _ => bail!("legacy ssh-rsa/SHA-1 signatures are not accepted"),
    }
}

pub fn verify_native_user_auth_from_config(
    config: &ServerConfig,
    client: &NativeClientHello,
    server: &NativeServerHello,
    auth: &NativeUserAuth,
    source_ip: Option<IpAddr>,
) -> Result<AuthorizedKey> {
    let authorized_keys = load_authorized_keys(&config.authorized_keys)?;
    verify_native_user_auth(client, server, auth, &authorized_keys, source_ip)
}

pub fn generate_native_ephemeral() -> (StaticSecret, [u8; 32]) {
    let secret = StaticSecret::random();
    let public = X25519PublicKey::from(&secret).to_bytes();
    (secret, public)
}

pub fn derive_native_session_key(
    local_secret: &StaticSecret,
    remote_public: [u8; 32],
    client: &NativeClientHello,
    server: &NativeServerHello,
) -> Result<[u8; 32]> {
    let remote_public = X25519PublicKey::from(remote_public);
    let shared = local_secret.diffie_hellman(&remote_public);
    anyhow::ensure!(
        shared.was_contributory(),
        "native key exchange produced non-contributory shared secret"
    );
    let mut salt = b"dosh/native/session-key/v1".to_vec();
    salt.extend(crypto::sha256(&bincode::serialize(client)?));
    salt.extend(crypto::sha256(&bincode::serialize(server)?));
    crypto::hkdf32(shared.as_bytes(), &salt, b"dosh/native/chacha20poly1305/v1")
}

/// Derive a rotated transport key for transport rekey (spec §11 / §9).
///
/// The rotated key is derived **independently of the handshake traffic keys**:
/// the input keying material is the current epoch's key (which both peers already
/// hold) mixed with fresh, server-generated `rekey_material` (32 bytes of CSPRNG
/// output, delivered confidentially inside an AEAD `Rekey` packet sealed under
/// the current key). The new `epoch` and the previous epoch's `session_key_id`
/// salt the derivation so each epoch's key is unique. It never re-derives from
/// the handshake DH output, satisfying the spec requirement that "rotated session
/// keys must be derived independently ... from fresh randomness" and "must not
/// reuse handshake traffic keys."
///
/// Both peers run this identically — the client never needs the server's
/// long-term secret, only the fresh `rekey_material` it receives in the `Rekey`
/// packet plus the current key it already shares.
pub fn derive_rekey_session_key(
    current_key: &[u8; 32],
    rekey_material: &[u8; 32],
    previous_session_key_id: &[u8; 16],
    epoch: u64,
) -> Result<[u8; 32]> {
    let mut ikm = Vec::with_capacity(64);
    ikm.extend_from_slice(current_key);
    ikm.extend_from_slice(rekey_material);
    let mut salt = b"dosh/native/rekey/v1".to_vec();
    salt.extend_from_slice(previous_session_key_id);
    salt.extend_from_slice(&epoch.to_be_bytes());
    crypto::hkdf32(&ikm, &salt, b"dosh/native/rekey/chacha20poly1305/v1")
}

pub fn load_ed25519_identity(path: &Path) -> Result<SigningKey> {
    load_ed25519_identity_with_passphrase(path, None)
}

pub fn load_ed25519_identity_with_passphrase(
    path: &Path,
    passphrase: Option<&str>,
) -> Result<SigningKey> {
    let private_key = ssh_key::PrivateKey::read_openssh_file(path)
        .with_context(|| format!("read OpenSSH identity {}", path.display()))?;
    let private_key = if private_key.is_encrypted() {
        let passphrase = passphrase
            .ok_or_else(|| anyhow::anyhow!("OpenSSH identity {} is encrypted", path.display()))?;
        private_key
            .decrypt(passphrase)
            .with_context(|| format!("decrypt OpenSSH identity {}", path.display()))?
    } else {
        private_key
    };
    let ed25519 = private_key
        .key_data()
        .ed25519()
        .ok_or_else(|| anyhow::anyhow!("OpenSSH identity {} is not ssh-ed25519", path.display()))?;
    ed25519_dalek::SigningKey::try_from(ed25519)
        .with_context(|| format!("parse ssh-ed25519 identity {}", path.display()))
}

pub fn load_native_identity(path: &Path) -> Result<ssh_key::PrivateKey> {
    load_native_identity_with_passphrase(path, None)
}

pub fn load_native_identity_with_passphrase(
    path: &Path,
    passphrase: Option<&str>,
) -> Result<ssh_key::PrivateKey> {
    let raw = fs::read_to_string(path).with_context(|| format!("read {}", path.display()))?;
    let private_key = ssh_key::PrivateKey::from_openssh(&raw)
        .with_context(|| format!("parse OpenSSH identity {}", path.display()))?;
    let private_key = if private_key.is_encrypted() {
        let passphrase = passphrase
            .ok_or_else(|| anyhow::anyhow!("OpenSSH identity {} is encrypted", path.display()))?;
        private_key
            .decrypt(passphrase)
            .with_context(|| format!("decrypt OpenSSH identity {}", path.display()))?
    } else {
        private_key
    };
    let algorithm = private_key.public_key().algorithm().as_str().to_string();
    anyhow::ensure!(
        is_supported_user_key_algorithm(&algorithm),
        "OpenSSH identity {} has unsupported native key algorithm {algorithm}",
        path.display()
    );
    Ok(private_key)
}

impl AuthorizedKey {
    fn ensure_native_allowed(
        &self,
        auth: &NativeUserAuth,
        source_ip: Option<IpAddr>,
    ) -> Result<()> {
        if !self.options.unsupported.is_empty() {
            bail!(
                "authorized key has unsupported options: {}",
                self.options.unsupported.join(",")
            );
        }
        if let Some(from) = &self.options.from {
            let Some(source_ip) = source_ip else {
                bail!("authorized key from= requires source address context");
            };
            if !source_matches_from(source_ip, from)? {
                bail!("authorized key from= does not permit source {source_ip}");
            }
        }
        if self.options.force_command.is_some() {
            bail!("authorized key command= is not supported for native Dosh terminal login");
        }
        if self.options.no_port_forwarding && !auth.requested_forwardings.is_empty() {
            bail!("authorized key forbids port forwarding");
        }
        if !self.options.permitopen.is_empty() {
            for forwarding in &auth.requested_forwardings {
                match forwarding.kind {
                    ForwardingKind::Local => {
                        if let (Some(host), Some(port)) =
                            (forwarding.target_host.as_ref(), forwarding.target_port)
                        {
                            let target = format!("{host}:{port}");
                            if !self
                                .options
                                .permitopen
                                .iter()
                                .any(|permit| permit == &target)
                            {
                                bail!("authorized key does not permit opening {target}");
                            }
                        }
                    }
                    ForwardingKind::Remote | ForwardingKind::Dynamic => {
                        bail!(
                            "authorized key permitopen= cannot authorize remote or dynamic forwarding"
                        );
                    }
                    // Agent forwarding does not open a host:port, so permitopen
                    // (which restricts which targets may be opened) does not apply;
                    // it is gated separately by the server's allow_agent_forwarding.
                    ForwardingKind::Agent => {}
                }
            }
        }
        Ok(())
    }
}

pub fn load_authorized_keys(paths: &[String]) -> Result<Vec<AuthorizedKey>> {
    let mut out = Vec::new();
    for path in paths {
        let path = expand_tilde(path);
        if !path.exists() {
            continue;
        }
        let raw = fs::read_to_string(&path).with_context(|| format!("read {}", path.display()))?;
        out.extend(
            parse_authorized_keys(&raw).with_context(|| format!("parse {}", path.display()))?,
        );
    }
    Ok(out)
}

pub fn parse_authorized_keys(raw: &str) -> Result<Vec<AuthorizedKey>> {
    raw.lines()
        .enumerate()
        .filter_map(|(index, line)| {
            let line = line.trim();
            if line.is_empty() || line.starts_with('#') {
                None
            } else {
                Some(parse_authorized_key_line(index + 1, line))
            }
        })
        .collect()
}

fn parse_authorized_key_line(line_number: usize, line: &str) -> Result<AuthorizedKey> {
    let fields = split_authorized_key_fields(line);
    anyhow::ensure!(
        fields.len() >= 2,
        "authorized_keys:{line_number}: expected key fields"
    );
    let (options, key_type_index) = if is_supported_user_key_algorithm(&fields[0]) {
        (AuthorizedKeyOptions::default(), 0)
    } else {
        (parse_authorized_key_options(&fields[0])?, 1)
    };
    let algorithm = fields
        .get(key_type_index)
        .with_context(|| format!("authorized_keys:{line_number}: missing key type"))?;
    let key_blob = fields
        .get(key_type_index + 1)
        .with_context(|| format!("authorized_keys:{line_number}: missing key blob"))?;
    let decoded = STANDARD
        .decode(key_blob)
        .with_context(|| format!("authorized_keys:{line_number}: decode key blob"))?;
    anyhow::ensure!(
        is_supported_user_key_algorithm(algorithm),
        "authorized_keys:{line_number}: unsupported key type {algorithm}"
    );
    validate_supported_public_key_blob(algorithm, &decoded)
        .with_context(|| format!("authorized_keys:{line_number}: parse {algorithm} key"))?;
    let key = if algorithm == "ssh-ed25519" {
        parse_ssh_ed25519_public_blob(&decoded)?.to_vec()
    } else {
        decoded
    };
    let comment = if fields.len() > key_type_index + 2 {
        Some(fields[key_type_index + 2..].join(" "))
    } else {
        None
    };
    Ok(AuthorizedKey {
        algorithm: algorithm.to_string(),
        key: key.to_vec(),
        options,
        comment,
    })
}

fn validate_supported_public_key_blob(algorithm: &str, blob: &[u8]) -> Result<()> {
    let blob_algorithm = ssh_public_key_blob_algorithm(blob)?;
    anyhow::ensure!(
        blob_algorithm == algorithm,
        "key blob type {blob_algorithm} does not match authorized_keys type {algorithm}"
    );
    match algorithm {
        "ssh-ed25519" => {
            parse_ssh_ed25519_public_blob(blob)?;
        }
        "ecdsa-sha2-nistp256" | "ssh-rsa" => {
            let _ = ssh_public_key_from_blob(blob)?;
        }
        _ => bail!("unsupported key type {algorithm}"),
    }
    Ok(())
}

fn ssh_public_key_blob_algorithm(blob: &[u8]) -> Result<String> {
    let mut cursor = blob;
    let algorithm = read_ssh_string(&mut cursor)?;
    Ok(String::from_utf8_lossy(algorithm).to_string())
}

fn ssh_public_key_from_blob(blob: &[u8]) -> Result<ssh_key::PublicKey> {
    let algorithm = ssh_public_key_blob_algorithm(blob)?;
    let encoded = STANDARD.encode(blob);
    ssh_key::PublicKey::from_openssh(&format!("{algorithm} {encoded}"))
        .with_context(|| format!("parse OpenSSH public key blob {algorithm}"))
}

fn ssh_public_blob_from_public_key(public_key: &ssh_key::PublicKey) -> Result<Vec<u8>> {
    let line = public_key
        .to_openssh()
        .context("encode OpenSSH public key")?;
    let mut fields = line.split_whitespace();
    let _algorithm = fields
        .next()
        .context("encoded public key missing algorithm")?;
    let encoded = fields.next().context("encoded public key missing blob")?;
    STANDARD
        .decode(encoded)
        .context("decode encoded OpenSSH public key blob")
}

fn split_authorized_key_fields(line: &str) -> Vec<String> {
    line.split_whitespace().map(ToString::to_string).collect()
}

fn parse_authorized_key_options(raw: &str) -> Result<AuthorizedKeyOptions> {
    let mut options = AuthorizedKeyOptions::default();
    for option in split_options(raw)? {
        if option == "restrict" {
            options.restricted = true;
        } else if option == "no-port-forwarding" {
            options.no_port_forwarding = true;
        } else if let Some(value) = option.strip_prefix("from=") {
            options.from = Some(strip_quotes(value).to_string());
        } else if let Some(value) = option.strip_prefix("command=") {
            options.force_command = Some(strip_quotes(value).to_string());
        } else if let Some(value) = option.strip_prefix("permitopen=") {
            options.permitopen.push(strip_quotes(value).to_string());
        } else {
            options.unsupported.push(option);
        }
    }
    Ok(options)
}

fn split_options(raw: &str) -> Result<Vec<String>> {
    let mut out = Vec::new();
    let mut current = String::new();
    let mut quoted = false;
    let mut escaped = false;
    for ch in raw.chars() {
        if escaped {
            current.push(ch);
            escaped = false;
            continue;
        }
        if ch == '\\' && quoted {
            escaped = true;
            continue;
        }
        if ch == '"' {
            quoted = !quoted;
            current.push(ch);
            continue;
        }
        if ch == ',' && !quoted {
            out.push(current);
            current = String::new();
            continue;
        }
        current.push(ch);
    }
    anyhow::ensure!(!quoted, "unterminated authorized_keys option quote");
    if !current.is_empty() {
        out.push(current);
    }
    Ok(out)
}

fn strip_quotes(raw: &str) -> &str {
    raw.strip_prefix('"')
        .and_then(|value| value.strip_suffix('"'))
        .unwrap_or(raw)
}

fn source_matches_from(source: IpAddr, raw: &str) -> Result<bool> {
    let mut matched_positive = false;
    for pattern in raw
        .split(',')
        .map(str::trim)
        .filter(|value| !value.is_empty())
    {
        let (negated, pattern) = pattern
            .strip_prefix('!')
            .map_or((false, pattern), |stripped| (true, stripped));
        let matched = source_pattern_matches(source, pattern)?;
        if negated && matched {
            return Ok(false);
        }
        if matched {
            matched_positive = true;
        }
    }
    Ok(matched_positive)
}

fn source_pattern_matches(source: IpAddr, pattern: &str) -> Result<bool> {
    if let Some((network, prefix)) = pattern.split_once('/') {
        let network = IpAddr::from_str(network)
            .with_context(|| format!("parse authorized_keys from= network {pattern:?}"))?;
        let prefix = prefix
            .parse::<u8>()
            .with_context(|| format!("parse authorized_keys from= prefix {pattern:?}"))?;
        return cidr_contains(network, prefix, source);
    }
    if pattern.contains('*') || pattern.contains('?') {
        return Ok(glob_matches(pattern, &source.to_string()));
    }
    match IpAddr::from_str(pattern) {
        Ok(ip) => Ok(ip == source),
        Err(_) => Ok(pattern == source.to_string()),
    }
}

fn cidr_contains(network: IpAddr, prefix: u8, source: IpAddr) -> Result<bool> {
    match (network, source) {
        (IpAddr::V4(network), IpAddr::V4(source)) => {
            anyhow::ensure!(prefix <= 32, "IPv4 from= prefix must be <= 32");
            let mask = if prefix == 0 {
                0
            } else {
                u32::MAX << (32 - prefix)
            };
            Ok((u32::from(network) & mask) == (u32::from(source) & mask))
        }
        (IpAddr::V6(network), IpAddr::V6(source)) => {
            anyhow::ensure!(prefix <= 128, "IPv6 from= prefix must be <= 128");
            let mask = if prefix == 0 {
                0
            } else {
                u128::MAX << (128 - prefix)
            };
            Ok((u128::from(network) & mask) == (u128::from(source) & mask))
        }
        _ => Ok(false),
    }
}

fn glob_matches(pattern: &str, value: &str) -> bool {
    let pattern = pattern.as_bytes();
    let value = value.as_bytes();
    let (mut p, mut v) = (0usize, 0usize);
    let mut star = None;
    let mut star_value = 0usize;
    while v < value.len() {
        if p < pattern.len() && (pattern[p] == b'?' || pattern[p] == value[v]) {
            p += 1;
            v += 1;
        } else if p < pattern.len() && pattern[p] == b'*' {
            star = Some(p);
            p += 1;
            star_value = v;
        } else if let Some(star_pos) = star {
            p = star_pos + 1;
            star_value += 1;
            v = star_value;
        } else {
            return false;
        }
    }
    while p < pattern.len() && pattern[p] == b'*' {
        p += 1;
    }
    p == pattern.len()
}

pub fn parse_ssh_ed25519_public_blob(blob: &[u8]) -> Result<[u8; 32]> {
    let mut cursor = blob;
    let key_type = read_ssh_string(&mut cursor)?;
    anyhow::ensure!(key_type == b"ssh-ed25519", "key blob type mismatch");
    let key = read_ssh_string(&mut cursor)?;
    anyhow::ensure!(key.len() == 32, "ssh-ed25519 key must be 32 bytes");
    anyhow::ensure!(cursor.is_empty(), "trailing data in ssh-ed25519 key blob");
    let mut out = [0u8; 32];
    out.copy_from_slice(key);
    Ok(out)
}

fn parse_ssh_rsa_public_blob(blob: &[u8]) -> Result<(&[u8], &[u8])> {
    let mut cursor = blob;
    let key_type = read_ssh_string(&mut cursor)?;
    anyhow::ensure!(key_type == b"ssh-rsa", "key blob type mismatch");
    let e = read_ssh_mpint(&mut cursor)?;
    let n = read_ssh_mpint(&mut cursor)?;
    anyhow::ensure!(cursor.is_empty(), "trailing data in ssh-rsa key blob");
    anyhow::ensure!(!e.is_empty(), "ssh-rsa exponent is empty");
    anyhow::ensure!(!n.is_empty(), "ssh-rsa modulus is empty");
    Ok((e, n))
}

pub fn ssh_ed25519_public_blob(public_key: &[u8; 32]) -> Vec<u8> {
    let mut out = Vec::new();
    write_ssh_string(&mut out, b"ssh-ed25519");
    write_ssh_string(&mut out, public_key);
    out
}

fn read_ssh_mpint<'a>(cursor: &mut &'a [u8]) -> Result<&'a [u8]> {
    let raw = read_ssh_string(cursor)?;
    let raw = raw.strip_prefix(&[0]).unwrap_or(raw);
    Ok(raw)
}

fn read_ssh_string<'a>(cursor: &mut &'a [u8]) -> Result<&'a [u8]> {
    anyhow::ensure!(cursor.len() >= 4, "truncated SSH string length");
    let len = u32::from_be_bytes(cursor[..4].try_into().unwrap()) as usize;
    *cursor = &cursor[4..];
    anyhow::ensure!(cursor.len() >= len, "truncated SSH string body");
    let (value, rest) = cursor.split_at(len);
    *cursor = rest;
    Ok(value)
}

fn write_ssh_string(out: &mut Vec<u8>, value: &[u8]) {
    out.extend_from_slice(&(value.len() as u32).to_be_bytes());
    out.extend_from_slice(value);
}

#[cfg(test)]
fn ssh_ed25519_authorized_key_line(signing_key: &SigningKey) -> String {
    let verifying = VerifyingKey::from(signing_key);
    let blob = ssh_ed25519_public_blob(&verifying.to_bytes());
    format!("ssh-ed25519 {} test-key", STANDARD.encode(blob))
}

pub fn known_host_line(host: &str, key: &HostPublicKey, source: &str, first_seen: u64) -> String {
    format!(
        "{} {} {} first-seen={} source={}",
        host,
        key.algorithm,
        URL_SAFE_NO_PAD.encode(key.key),
        first_seen,
        source
    )
}

pub fn parse_known_hosts(raw: &str) -> Result<Vec<KnownHost>> {
    raw.lines()
        .enumerate()
        .filter_map(|(index, line)| {
            let line = line.trim();
            if line.is_empty() || line.starts_with('#') {
                None
            } else {
                Some(parse_known_host_line(index + 1, line))
            }
        })
        .collect()
}

pub fn verify_known_host(path: &Path, host: &str, key: &HostPublicKey) -> Result<KnownHostStatus> {
    if !path.exists() {
        return Ok(KnownHostStatus::Unknown);
    }
    let raw = fs::read_to_string(path).with_context(|| format!("read {}", path.display()))?;
    let entries = parse_known_hosts(&raw)?;
    let Some(existing) = entries.iter().find(|entry| entry.host == host) else {
        return Ok(KnownHostStatus::Unknown);
    };
    if existing.algorithm == key.algorithm && existing.key == key.key {
        Ok(KnownHostStatus::Trusted)
    } else {
        Ok(KnownHostStatus::Mismatch {
            expected: host_fingerprint(&HostPublicKey {
                algorithm: existing.algorithm.clone(),
                key: existing.key,
            }),
            actual: host_fingerprint(key),
        })
    }
}

fn parse_known_host_line(line_number: usize, line: &str) -> Result<KnownHost> {
    let mut parts = line.split_whitespace();
    let host = parts
        .next()
        .with_context(|| format!("known_hosts:{line_number}: missing host"))?;
    let algorithm = parts
        .next()
        .with_context(|| format!("known_hosts:{line_number}: missing algorithm"))?;
    if algorithm != HOST_KEY_ALGORITHM {
        bail!("known_hosts:{line_number}: unsupported algorithm {algorithm}");
    }
    let key_raw = parts
        .next()
        .with_context(|| format!("known_hosts:{line_number}: missing key"))?;
    let decoded = URL_SAFE_NO_PAD
        .decode(key_raw)
        .with_context(|| format!("known_hosts:{line_number}: decode key"))?;
    anyhow::ensure!(
        decoded.len() == 32,
        "known_hosts:{line_number}: host key must be 32 bytes"
    );
    let mut key = [0u8; 32];
    key.copy_from_slice(&decoded);
    let mut first_seen = 0;
    let mut source = "unknown".to_string();
    for part in parts {
        if let Some(value) = part.strip_prefix("first-seen=") {
            first_seen = value.parse().unwrap_or(0);
        } else if let Some(value) = part.strip_prefix("source=") {
            source = value.to_string();
        }
    }
    Ok(KnownHost {
        host: host.to_string(),
        algorithm: algorithm.to_string(),
        key,
        first_seen,
        source,
    })
}

pub fn trust_host(
    path: &Path,
    host: &str,
    key: &HostPublicKey,
    source: &str,
    replace: bool,
) -> Result<TrustResult> {
    let raw = if path.exists() {
        fs::read_to_string(path).with_context(|| format!("read {}", path.display()))?
    } else {
        String::new()
    };
    let mut entries = parse_known_hosts(&raw)?;
    if let Some(existing) = entries.iter().find(|entry| entry.host == host) {
        if existing.key == key.key && existing.algorithm == key.algorithm {
            return Ok(TrustResult::AlreadyTrusted);
        }
        if !replace {
            bail!(
                "Dosh host key mismatch for {host}: existing {}, new {}",
                host_fingerprint(&HostPublicKey {
                    algorithm: existing.algorithm.clone(),
                    key: existing.key,
                }),
                host_fingerprint(key)
            );
        }
        entries.retain(|entry| entry.host != host);
    }
    entries.push(KnownHost {
        host: host.to_string(),
        algorithm: key.algorithm.clone(),
        key: key.key,
        first_seen: now_secs()?,
        source: source.to_string(),
    });
    write_known_hosts(path, &entries)
}

pub fn remove_trusted_host(path: &Path, host: &str) -> Result<bool> {
    if !path.exists() {
        return Ok(false);
    }
    let raw = fs::read_to_string(path).with_context(|| format!("read {}", path.display()))?;
    let mut entries = parse_known_hosts(&raw)?;
    let before = entries.len();
    entries.retain(|entry| entry.host != host);
    if entries.len() == before {
        return Ok(false);
    }
    write_known_host_entries(path, &entries)?;
    Ok(true)
}

fn write_known_hosts(path: &Path, entries: &[KnownHost]) -> Result<TrustResult> {
    write_known_host_entries(path, entries)?;
    Ok(TrustResult::Trusted)
}

fn write_known_host_entries(path: &Path, entries: &[KnownHost]) -> Result<()> {
    if let Some(parent) = path.parent() {
        fs::create_dir_all(parent).with_context(|| format!("create {}", parent.display()))?;
    }
    let mut out = String::new();
    for entry in entries {
        out.push_str(&known_host_line(
            &entry.host,
            &HostPublicKey {
                algorithm: entry.algorithm.clone(),
                key: entry.key,
            },
            &entry.source,
            entry.first_seen,
        ));
        out.push('\n');
    }
    let mut options = fs::OpenOptions::new();
    options.create(true).truncate(true).write(true);
    #[cfg(unix)]
    options.mode(0o600);
    let mut file = options
        .open(path)
        .with_context(|| format!("write {}", path.display()))?;
    file.write_all(out.as_bytes())
        .with_context(|| format!("write {}", path.display()))
}

#[derive(Debug, Clone, Copy, PartialEq, Eq)]
pub enum TrustResult {
    AlreadyTrusted,
    Trusted,
}

#[derive(Debug, Clone, PartialEq, Eq)]
pub enum KnownHostStatus {
    Unknown,
    Trusted,
    Mismatch { expected: String, actual: String },
}

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

    #[test]
    fn host_public_key_line_round_trips() {
        let signing = SigningKey::from_bytes(&[7u8; 32]);
        let public = host_public_key(&signing);
        let line = host_public_key_line(&public);
        let parsed = parse_host_public_key_line(&line).unwrap();
        assert_eq!(parsed, public);
        assert!(host_fingerprint(&public).starts_with("SHA256:"));
    }

    #[test]
    fn known_host_trust_rejects_mismatch_without_replace() {
        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("known_hosts");
        let first = host_public_key(&SigningKey::from_bytes(&[1u8; 32]));
        let second = host_public_key(&SigningKey::from_bytes(&[2u8; 32]));

        assert_eq!(
            trust_host(&path, "homelab", &first, "ssh", false).unwrap(),
            TrustResult::Trusted
        );
        assert_eq!(
            trust_host(&path, "homelab", &first, "ssh", false).unwrap(),
            TrustResult::AlreadyTrusted
        );
        assert!(trust_host(&path, "homelab", &second, "ssh", false).is_err());
        assert_eq!(
            trust_host(&path, "homelab", &second, "ssh", true).unwrap(),
            TrustResult::Trusted
        );
    }

    #[test]
    fn known_host_verification_reports_trusted_unknown_and_mismatch() {
        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("known_hosts");
        let first = host_public_key(&SigningKey::from_bytes(&[1u8; 32]));
        let second = host_public_key(&SigningKey::from_bytes(&[2u8; 32]));

        assert_eq!(
            verify_known_host(&path, "homelab", &first).unwrap(),
            KnownHostStatus::Unknown
        );
        trust_host(&path, "homelab", &first, "ssh", false).unwrap();
        assert_eq!(
            verify_known_host(&path, "homelab", &first).unwrap(),
            KnownHostStatus::Trusted
        );
        assert!(matches!(
            verify_known_host(&path, "homelab", &second).unwrap(),
            KnownHostStatus::Mismatch { .. }
        ));
    }

    #[test]
    fn server_hello_signature_round_trips() {
        let signing = SigningKey::from_bytes(&[3u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&signing);
        sign_server_hello(&signing, &client, &mut server).unwrap();
        verify_server_hello(&client, &server).unwrap();
        server.auth_challenge = [7u8; 32];
        assert!(verify_server_hello(&client, &server).is_err());
    }

    #[test]
    fn authorized_keys_parses_ed25519() {
        let signing = SigningKey::from_bytes(&[8u8; 32]);
        let raw = ssh_ed25519_authorized_key_line(&signing);
        let parsed = parse_authorized_keys(&raw).unwrap();
        assert_eq!(parsed.len(), 1);
        assert_eq!(parsed[0].algorithm, "ssh-ed25519");
        assert_eq!(
            parsed[0].key,
            VerifyingKey::from(&signing).to_bytes().to_vec()
        );
        assert_eq!(parsed[0].comment.as_deref(), Some("test-key"));
    }

    #[test]
    fn native_user_auth_accepts_authorized_key_and_rejects_removed_key() {
        let host_signing = SigningKey::from_bytes(&[3u8; 32]);
        let user_signing = SigningKey::from_bytes(&[9u8; 32]);
        let other_signing = SigningKey::from_bytes(&[10u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let auth = sign_user_auth(&user_signing, &client, &server, Vec::new()).unwrap();
        let authorized =
            parse_authorized_keys(&ssh_ed25519_authorized_key_line(&user_signing)).unwrap();

        verify_native_user_auth(&client, &server, &auth, &authorized, None).unwrap();

        let removed =
            parse_authorized_keys(&ssh_ed25519_authorized_key_line(&other_signing)).unwrap();
        assert!(verify_native_user_auth(&client, &server, &auth, &removed, None).is_err());
    }

    #[test]
    fn native_user_auth_accepts_ecdsa_p256_private_key() {
        let mut rng = rand::rngs::OsRng;
        let private = ssh_key::PrivateKey::random(
            &mut rng,
            ssh_key::Algorithm::Ecdsa {
                curve: ssh_key::EcdsaCurve::NistP256,
            },
        )
        .unwrap();
        let host_signing = SigningKey::from_bytes(&[10u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let auth = sign_user_auth_with_private_key(&private, &client, &server, Vec::new()).unwrap();
        let authorized =
            parse_authorized_keys(&private.public_key().to_openssh().unwrap()).unwrap();

        assert_eq!(auth.public_key_algorithm, "ecdsa-sha2-nistp256");
        verify_native_user_auth(&client, &server, &auth, &authorized, None).unwrap();
    }

    #[test]
    fn native_user_auth_accepts_rsa_sha2_private_key() {
        let mut rng = rand::rngs::OsRng;
        let private =
            ssh_key::PrivateKey::random(&mut rng, ssh_key::Algorithm::Rsa { hash: None }).unwrap();
        let host_signing = SigningKey::from_bytes(&[11u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let auth = sign_user_auth_with_private_key(&private, &client, &server, Vec::new()).unwrap();
        let authorized =
            parse_authorized_keys(&private.public_key().to_openssh().unwrap()).unwrap();

        assert_eq!(auth.public_key_algorithm, "rsa-sha2-512");
        verify_native_user_auth(&client, &server, &auth, &authorized, None).unwrap();
    }

    #[test]
    fn native_user_auth_rejects_tampered_transcript() {
        let host_signing = SigningKey::from_bytes(&[3u8; 32]);
        let user_signing = SigningKey::from_bytes(&[9u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let auth = sign_user_auth(&user_signing, &client, &server, Vec::new()).unwrap();
        let authorized =
            parse_authorized_keys(&ssh_ed25519_authorized_key_line(&user_signing)).unwrap();
        let mut tampered = client.clone();
        tampered.requested_session = "other".to_string();

        assert!(verify_native_user_auth(&tampered, &server, &auth, &authorized, None).is_err());
    }

    #[test]
    fn native_user_auth_fails_closed_on_unsupported_authorized_key_options() {
        let host_signing = SigningKey::from_bytes(&[3u8; 32]);
        let user_signing = SigningKey::from_bytes(&[9u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let auth = sign_user_auth(&user_signing, &client, &server, Vec::new()).unwrap();
        let raw = format!(
            "no-agent-forwarding {}",
            ssh_ed25519_authorized_key_line(&user_signing)
        );
        let authorized = parse_authorized_keys(&raw).unwrap();

        assert!(verify_native_user_auth(&client, &server, &auth, &authorized, None).is_err());
    }

    #[test]
    fn native_user_auth_enforces_from_source_patterns() {
        let host_signing = SigningKey::from_bytes(&[3u8; 32]);
        let user_signing = SigningKey::from_bytes(&[9u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let auth = sign_user_auth(&user_signing, &client, &server, Vec::new()).unwrap();
        let authorized = parse_authorized_keys(&format!(
            "from=\"127.0.0.1,192.168.1.0/24,!192.168.1.66\" {}",
            ssh_ed25519_authorized_key_line(&user_signing)
        ))
        .unwrap();

        verify_native_user_auth(
            &client,
            &server,
            &auth,
            &authorized,
            Some("127.0.0.1".parse().unwrap()),
        )
        .unwrap();
        verify_native_user_auth(
            &client,
            &server,
            &auth,
            &authorized,
            Some("192.168.1.42".parse().unwrap()),
        )
        .unwrap();
        assert!(
            verify_native_user_auth(
                &client,
                &server,
                &auth,
                &authorized,
                Some("192.168.1.66".parse().unwrap()),
            )
            .is_err()
        );
        assert!(
            verify_native_user_auth(
                &client,
                &server,
                &auth,
                &authorized,
                Some("10.0.0.1".parse().unwrap()),
            )
            .is_err()
        );
        assert!(verify_native_user_auth(&client, &server, &auth, &authorized, None).is_err());
    }

    #[test]
    fn load_ed25519_identity_reads_openssh_private_key() {
        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("id_ed25519");
        let signing = SigningKey::from_bytes(&[11u8; 32]);
        let keypair = ssh_key::private::Ed25519Keypair::from(&signing);
        let private =
            ssh_key::PrivateKey::new(ssh_key::private::KeypairData::from(keypair), "").unwrap();
        private
            .write_openssh_file(&path, ssh_key::LineEnding::LF)
            .unwrap();

        let loaded = load_ed25519_identity(&path).unwrap();
        assert_eq!(
            VerifyingKey::from(&loaded).to_bytes(),
            VerifyingKey::from(&signing).to_bytes()
        );
    }

    #[test]
    fn load_ed25519_identity_decrypts_encrypted_openssh_private_key() {
        let dir = tempfile::tempdir().unwrap();
        let path = dir.path().join("id_ed25519");
        let signing = SigningKey::from_bytes(&[12u8; 32]);
        let keypair = ssh_key::private::Ed25519Keypair::from(&signing);
        let private =
            ssh_key::PrivateKey::new(ssh_key::private::KeypairData::from(keypair), "").unwrap();
        let encrypted = private
            .encrypt(&mut rand::rngs::OsRng, "correct horse battery staple")
            .unwrap();
        encrypted
            .write_openssh_file(&path, ssh_key::LineEnding::LF)
            .unwrap();

        assert!(load_ed25519_identity(&path).is_err());
        assert!(load_ed25519_identity_with_passphrase(&path, Some("wrong")).is_err());
        let loaded =
            load_ed25519_identity_with_passphrase(&path, Some("correct horse battery staple"))
                .unwrap();
        assert_eq!(
            VerifyingKey::from(&loaded).to_bytes(),
            VerifyingKey::from(&signing).to_bytes()
        );
    }

    #[test]
    fn native_session_key_derivation_matches_and_binds_transcript() {
        let host_signing = SigningKey::from_bytes(&[3u8; 32]);
        let (client_secret, client_public) = generate_native_ephemeral();
        let (server_secret, server_public) = generate_native_ephemeral();
        let mut client = test_client_hello();
        client.client_ephemeral_public = client_public;
        let mut server = test_server_hello(&host_signing);
        server.server_ephemeral_public = server_public;
        sign_server_hello(&host_signing, &client, &mut server).unwrap();

        let client_key = derive_native_session_key(
            &client_secret,
            server.server_ephemeral_public,
            &client,
            &server,
        )
        .unwrap();
        let server_key = derive_native_session_key(
            &server_secret,
            client.client_ephemeral_public,
            &client,
            &server,
        )
        .unwrap();
        assert_eq!(client_key, server_key);

        let mut tampered = server.clone();
        tampered.auth_challenge = [99u8; 32];
        let tampered_key = derive_native_session_key(
            &client_secret,
            tampered.server_ephemeral_public,
            &client,
            &tampered,
        )
        .unwrap();
        assert_ne!(client_key, tampered_key);
    }

    #[test]
    fn native_user_auth_enforces_no_port_forwarding_and_permitopen() {
        let host_signing = SigningKey::from_bytes(&[3u8; 32]);
        let user_signing = SigningKey::from_bytes(&[9u8; 32]);
        let client = test_client_hello();
        let mut server = test_server_hello(&host_signing);
        sign_server_hello(&host_signing, &client, &mut server).unwrap();
        let forward = ForwardingRequest {
            kind: ForwardingKind::Local,
            bind_host: None,
            listen_port: 8080,
            target_host: Some("127.0.0.1".to_string()),
            target_port: Some(80),
        };
        let auth = sign_user_auth(&user_signing, &client, &server, vec![forward]).unwrap();
        let no_forwarding = parse_authorized_keys(&format!(
            "no-port-forwarding {}",
            ssh_ed25519_authorized_key_line(&user_signing)
        ))
        .unwrap();
        assert!(verify_native_user_auth(&client, &server, &auth, &no_forwarding, None).is_err());

        let permitted = parse_authorized_keys(&format!(
            "permitopen=\"127.0.0.1:80\" {}",
            ssh_ed25519_authorized_key_line(&user_signing)
        ))
        .unwrap();
        verify_native_user_auth(&client, &server, &auth, &permitted, None).unwrap();

        let denied = parse_authorized_keys(&format!(
            "permitopen=\"127.0.0.1:81\" {}",
            ssh_ed25519_authorized_key_line(&user_signing)
        ))
        .unwrap();
        assert!(verify_native_user_auth(&client, &server, &auth, &denied, None).is_err());

        let dynamic = ForwardingRequest {
            kind: ForwardingKind::Dynamic,
            bind_host: Some("127.0.0.1".to_string()),
            listen_port: 1080,
            target_host: None,
            target_port: None,
        };
        let dynamic_auth = sign_user_auth(&user_signing, &client, &server, vec![dynamic]).unwrap();
        assert!(
            verify_native_user_auth(&client, &server, &dynamic_auth, &no_forwarding, None).is_err()
        );
        assert!(
            verify_native_user_auth(&client, &server, &dynamic_auth, &permitted, None).is_err()
        );
    }

    fn test_client_hello() -> NativeClientHello {
        NativeClientHello {
            protocol_version: NATIVE_PROTOCOL_VERSION,
            client_random: [1u8; 32],
            client_ephemeral_public: [2u8; 32],
            requested_host: "homelab".to_string(),
            requested_user: "alice".to_string(),
            requested_session: "term".to_string(),
            requested_mode: "read-write".to_string(),
            terminal_size: (80, 24),
            supported_aead: vec!["chacha20poly1305".to_string()],
            supported_user_key_algorithms: vec!["ssh-ed25519".to_string()],
            cached_host_key_fingerprint: None,
            attach_ticket_envelope: None,
            requested_env: Vec::new(),
        }
    }

    fn test_server_hello(signing: &SigningKey) -> NativeServerHello {
        NativeServerHello {
            protocol_version: NATIVE_PROTOCOL_VERSION,
            server_random: [4u8; 32],
            server_ephemeral_public: [5u8; 32],
            host_key: host_public_key(signing),
            chosen_aead: "chacha20poly1305".to_string(),
            server_key_epoch: 1,
            auth_challenge: [6u8; 32],
            rate_limit_remaining: Some(30),
            host_signature: Vec::new(),
        }
    }
}