"""
muxplex/tls.py — TLS certificate generation and inspection.

Provides:
  generate_self_signed(cert_path, key_path, hostnames=None, days_valid=3650)
  generate_local_ca(ca_cert_path, ca_key_path, days_valid=3650)
  generate_leaf_signed_by_ca(ca_cert_path, ca_key_path, leaf_cert_path,
                             leaf_key_path, hostnames, ip_addresses,
                             days_valid=397)
  get_cert_info(cert_path)
"""

import ipaddress
import socket
from datetime import datetime, timezone
from pathlib import Path


def _default_hostnames() -> list[str]:
    hostname = socket.gethostname()
    return [hostname, f"{hostname}.local", "localhost"]


def _default_lan_ip() -> str | None:
    """Detect the primary outbound IPv4 address.

    Returns the local IP that would be used to reach an external host
    (no packets are actually sent — we use a connected UDP socket to ask
    the kernel which interface would route the traffic). Returns None on
    failure (no network, all-loopback configuration, etc.).
    """
    s = socket.socket(socket.AF_INET, socket.SOCK_DGRAM)
    try:
        # 8.8.8.8:80 is a routing target; UDP connect doesn't transmit.
        s.connect(("8.8.8.8", 80))
        ip = s.getsockname()[0]
    except OSError:
        return None
    finally:
        s.close()
    if ip in ("0.0.0.0", "127.0.0.1"):
        return None
    return ip


def _default_tailnet_name() -> str | None:
    """Return this host's MagicDNS name (e.g. 'spark-1.tail8f3c4e.ts.net'),
    or None if Tailscale is not installed / not connected / has no DNSName.

    Best-effort and short-timeout — failure is silent and returns None.
    """
    import json
    import shutil
    import subprocess

    if not shutil.which("tailscale"):
        return None
    try:
        result = subprocess.run(
            ["tailscale", "status", "--self", "--json"],
            timeout=5,
            capture_output=True,
            text=True,
        )
    except (subprocess.TimeoutExpired, OSError):
        return None
    if result.returncode != 0:
        return None
    try:
        data = json.loads(result.stdout)
    except json.JSONDecodeError:
        return None
    self_info = data.get("Self") or {}
    dns_name = self_info.get("DNSName", "") or data.get("DNSName", "")
    if not dns_name:
        return None
    return dns_name.rstrip(".")


def generate_self_signed(
    cert_path,
    key_path,
    hostnames: list[str] | None = None,
    days_valid: int = 3650,
) -> dict:
    """Generate a self-signed TLS certificate and private key.

    Args:
        cert_path: Destination path for the certificate PEM file.
        key_path:  Destination path for the private key PEM file.
        hostnames: DNS names to include. Defaults to [hostname, hostname.local, localhost].
        days_valid: Certificate validity period in days. Default 3650 (≈10 years).

    Returns:
        dict with keys: method, cert_path, key_path, hostnames, expires.
    """
    from cryptography import x509
    from cryptography.hazmat.primitives import hashes, serialization
    from cryptography.hazmat.primitives.asymmetric import rsa
    from cryptography.x509.oid import NameOID

    if hostnames is None:
        hostnames = _default_hostnames()

    cert_path = Path(cert_path)
    key_path = Path(key_path)

    # Create parent directories if needed
    cert_path.parent.mkdir(parents=True, exist_ok=True)
    key_path.parent.mkdir(parents=True, exist_ok=True)

    # Generate RSA 2048-bit private key
    private_key = rsa.generate_private_key(
        public_exponent=65537,
        key_size=2048,
    )

    # Build subject / issuer with CN = first hostname, O = muxplex
    subject = issuer = x509.Name(
        [
            x509.NameAttribute(NameOID.COMMON_NAME, hostnames[0]),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "muxplex"),
        ]
    )

    # Build SAN extension: DNS names for all hostnames + loopback IPs
    san_entries: list[x509.GeneralName] = [x509.DNSName(h) for h in hostnames]
    san_entries.append(x509.IPAddress(ipaddress.IPv4Address("127.0.0.1")))
    san_entries.append(x509.IPAddress(ipaddress.IPv6Address("::1")))

    now = datetime.now(timezone.utc)

    # Build the certificate
    cert = (
        x509.CertificateBuilder()
        .subject_name(subject)
        .issuer_name(issuer)
        .public_key(private_key.public_key())
        .serial_number(x509.random_serial_number())
        .not_valid_before(now)
        .not_valid_after(
            datetime.fromtimestamp(
                now.timestamp() + days_valid * 86400,
                tz=timezone.utc,
            )
        )
        .add_extension(
            x509.SubjectAlternativeName(san_entries),
            critical=False,
        )
        .sign(private_key, hashes.SHA256())
    )

    try:
        expires = cert.not_valid_after_utc  # type: ignore[attr-defined]
    except AttributeError:
        expires = cert.not_valid_after  # type: ignore[attr-defined]

    # Write key PEM — create file with restricted permissions before writing
    key_pem = private_key.private_bytes(
        encoding=serialization.Encoding.PEM,
        format=serialization.PrivateFormat.TraditionalOpenSSL,
        encryption_algorithm=serialization.NoEncryption(),
    )
    key_path.touch(mode=0o600, exist_ok=True)
    key_path.write_bytes(key_pem)
    key_path.chmod(0o600)

    # Write cert PEM
    cert_pem = cert.public_bytes(serialization.Encoding.PEM)
    cert_path.write_bytes(cert_pem)

    return {
        "method": "selfsigned",
        "cert_path": str(cert_path),
        "key_path": str(key_path),
        "hostnames": hostnames,
        "expires": expires,
    }


def generate_local_ca(
    ca_cert_path,
    ca_key_path,
    days_valid: int = 3650,
    common_name: str = "muxplex Local CA",
) -> dict:
    """Generate (or reuse) a persistent local CA for signing leaf certs.

    The CA is suitable for installation into OS / browser trust stores:
    BasicConstraints CA:TRUE (path_length=0), KeyUsage keyCertSign+cRLSign,
    SubjectKeyIdentifier present.

    Idempotent: if both ca_cert_path and ca_key_path already exist, this
    function does nothing and returns metadata for the existing CA. To
    regenerate, delete the files first.

    Args:
        ca_cert_path: Destination path for the CA certificate PEM file.
        ca_key_path:  Destination path for the CA private key PEM file.
        days_valid:   CA validity period in days. Default 3650 (~10 years).
        common_name:  CN for the CA's subject/issuer name.

    Returns:
        dict with keys: ca_cert_path, ca_key_path, common_name, expires,
        regenerated (True if newly generated, False if reused).
    """
    from cryptography import x509
    from cryptography.hazmat.primitives import hashes, serialization
    from cryptography.hazmat.primitives.asymmetric import rsa
    from cryptography.x509.oid import NameOID

    ca_cert_path = Path(ca_cert_path)
    ca_key_path = Path(ca_key_path)

    if ca_cert_path.exists() and ca_key_path.exists():
        info = get_cert_info(ca_cert_path)
        return {
            "ca_cert_path": str(ca_cert_path),
            "ca_key_path": str(ca_key_path),
            "common_name": common_name,
            "expires": info["expires"] if info else None,
            "regenerated": False,
        }

    ca_cert_path.parent.mkdir(parents=True, exist_ok=True)
    ca_key_path.parent.mkdir(parents=True, exist_ok=True)

    # 4096-bit RSA for the long-lived CA
    ca_key = rsa.generate_private_key(public_exponent=65537, key_size=4096)

    subject = issuer = x509.Name(
        [
            x509.NameAttribute(NameOID.COMMON_NAME, common_name),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "muxplex"),
        ]
    )

    now = datetime.now(timezone.utc)

    cert = (
        x509.CertificateBuilder()
        .subject_name(subject)
        .issuer_name(issuer)
        .public_key(ca_key.public_key())
        .serial_number(x509.random_serial_number())
        .not_valid_before(now)
        .not_valid_after(
            datetime.fromtimestamp(
                now.timestamp() + days_valid * 86400, tz=timezone.utc
            )
        )
        .add_extension(
            x509.BasicConstraints(ca=True, path_length=0),
            critical=True,
        )
        .add_extension(
            x509.KeyUsage(
                digital_signature=False,
                content_commitment=False,
                key_encipherment=False,
                data_encipherment=False,
                key_agreement=False,
                key_cert_sign=True,
                crl_sign=True,
                encipher_only=False,
                decipher_only=False,
            ),
            critical=True,
        )
        .add_extension(
            x509.SubjectKeyIdentifier.from_public_key(ca_key.public_key()),
            critical=False,
        )
        .sign(ca_key, hashes.SHA256())
    )

    # Write key with restricted permissions (touch 0o600 BEFORE write to
    # avoid the world-readable window during file creation).
    key_pem = ca_key.private_bytes(
        encoding=serialization.Encoding.PEM,
        format=serialization.PrivateFormat.TraditionalOpenSSL,
        encryption_algorithm=serialization.NoEncryption(),
    )
    ca_key_path.touch(mode=0o600, exist_ok=True)
    ca_key_path.write_bytes(key_pem)
    ca_key_path.chmod(0o600)

    cert_pem = cert.public_bytes(serialization.Encoding.PEM)
    ca_cert_path.write_bytes(cert_pem)

    try:
        expires = cert.not_valid_after_utc  # type: ignore[attr-defined]
    except AttributeError:
        expires = cert.not_valid_after  # type: ignore[attr-defined]

    return {
        "ca_cert_path": str(ca_cert_path),
        "ca_key_path": str(ca_key_path),
        "common_name": common_name,
        "expires": expires,
        "regenerated": True,
    }


def generate_leaf_signed_by_ca(
    ca_cert_path,
    ca_key_path,
    leaf_cert_path,
    leaf_key_path,
    hostnames: list[str],
    ip_addresses: list[str] | None = None,
    days_valid: int = 397,
) -> dict:
    """Generate a leaf TLS certificate signed by a local CA.

    The leaf is suitable for serving HTTPS: KeyUsage digitalSignature +
    keyEncipherment, ExtendedKeyUsage serverAuth, SAN populated from
    hostnames + ip_addresses, AuthorityKeyIdentifier linked to the CA.

    Args:
        ca_cert_path:   Path to the CA certificate PEM.
        ca_key_path:    Path to the CA private key PEM.
        leaf_cert_path: Destination for the leaf certificate.
        leaf_key_path:  Destination for the leaf private key.
        hostnames:      DNS names to include in SAN. The first is also used
                        as the leaf's CN.
        ip_addresses:   Optional IPv4/IPv6 strings to include as IP SAN
                        entries. Invalid entries are skipped silently.
        days_valid:     Leaf validity in days. Default 397 — just under
                        the CA/B Forum 398-day enforcement ceiling that
                        Apple/Chrome also apply to privately-installed
                        roots in many recent versions.

    Returns:
        dict with keys: method, cert_path, key_path, hostnames, expires.
    """
    from cryptography import x509
    from cryptography.hazmat.primitives import hashes, serialization
    from cryptography.hazmat.primitives.asymmetric import rsa
    from cryptography.x509.oid import ExtendedKeyUsageOID, NameOID

    if not hostnames:
        raise ValueError("at least one hostname is required for leaf certificate")

    ca_cert_path = Path(ca_cert_path)
    ca_key_path = Path(ca_key_path)
    leaf_cert_path = Path(leaf_cert_path)
    leaf_key_path = Path(leaf_key_path)

    leaf_cert_path.parent.mkdir(parents=True, exist_ok=True)
    leaf_key_path.parent.mkdir(parents=True, exist_ok=True)

    ca_cert = x509.load_pem_x509_certificate(ca_cert_path.read_bytes())
    ca_key = serialization.load_pem_private_key(ca_key_path.read_bytes(), password=None)

    leaf_key = rsa.generate_private_key(public_exponent=65537, key_size=2048)

    subject = x509.Name(
        [
            x509.NameAttribute(NameOID.COMMON_NAME, hostnames[0]),
            x509.NameAttribute(NameOID.ORGANIZATION_NAME, "muxplex"),
        ]
    )

    san_entries: list[x509.GeneralName] = [x509.DNSName(h) for h in hostnames]
    valid_ips: list[str] = []
    if ip_addresses:
        for ip_str in ip_addresses:
            try:
                addr = ipaddress.ip_address(ip_str)
            except ValueError:
                continue
            san_entries.append(x509.IPAddress(addr))
            valid_ips.append(ip_str)

    now = datetime.now(timezone.utc)

    cert = (
        x509.CertificateBuilder()
        .subject_name(subject)
        .issuer_name(ca_cert.subject)
        .public_key(leaf_key.public_key())
        .serial_number(x509.random_serial_number())
        .not_valid_before(now)
        .not_valid_after(
            datetime.fromtimestamp(
                now.timestamp() + days_valid * 86400, tz=timezone.utc
            )
        )
        .add_extension(
            x509.SubjectAlternativeName(san_entries),
            critical=False,
        )
        .add_extension(
            x509.BasicConstraints(ca=False, path_length=None),
            critical=True,
        )
        .add_extension(
            x509.KeyUsage(
                digital_signature=True,
                content_commitment=False,
                key_encipherment=True,
                data_encipherment=False,
                key_agreement=False,
                key_cert_sign=False,
                crl_sign=False,
                encipher_only=False,
                decipher_only=False,
            ),
            critical=True,
        )
        .add_extension(
            x509.ExtendedKeyUsage([ExtendedKeyUsageOID.SERVER_AUTH]),
            critical=False,
        )
        .add_extension(
            x509.SubjectKeyIdentifier.from_public_key(leaf_key.public_key()),
            critical=False,
        )
        .add_extension(
            x509.AuthorityKeyIdentifier.from_issuer_public_key(ca_cert.public_key()),  # type: ignore[arg-type]
            critical=False,
        )
        .sign(ca_key, hashes.SHA256())  # type: ignore[arg-type]
    )

    key_pem = leaf_key.private_bytes(
        encoding=serialization.Encoding.PEM,
        format=serialization.PrivateFormat.TraditionalOpenSSL,
        encryption_algorithm=serialization.NoEncryption(),
    )
    leaf_key_path.touch(mode=0o600, exist_ok=True)
    leaf_key_path.write_bytes(key_pem)
    leaf_key_path.chmod(0o600)

    cert_pem = cert.public_bytes(serialization.Encoding.PEM)
    leaf_cert_path.write_bytes(cert_pem)

    try:
        expires = cert.not_valid_after_utc  # type: ignore[attr-defined]
    except AttributeError:
        expires = cert.not_valid_after  # type: ignore[attr-defined]

    # Combined display list: DNS names + stringified IPs (for the success
    # message in the CLI).
    display_hostnames = list(hostnames) + valid_ips

    return {
        "method": "ca",
        "cert_path": str(leaf_cert_path),
        "key_path": str(leaf_key_path),
        "hostnames": display_hostnames,
        "expires": expires,
    }


def detect_tailscale() -> dict | None:
    """Probe for Tailscale and return connection info if available.

    Checks whether the Tailscale CLI is installed, verifies the node is
    connected, and confirms HTTPS certificate domains are enabled.

    Returns:
        dict with keys: hostname (str), ips (list[str]), cert_domains (list[str])
        if Tailscale is installed, connected, and cert domains are configured.
        Returns None if any of these conditions are not met.
    """
    import json
    import shutil
    import subprocess

    if not shutil.which("tailscale"):
        return None

    try:
        result = subprocess.run(
            ["tailscale", "status", "--self", "--json"],
            timeout=10,
            capture_output=True,
            text=True,
        )
    except (subprocess.TimeoutExpired, OSError):
        return None

    if result.returncode != 0:
        return None

    try:
        data = json.loads(result.stdout)
    except json.JSONDecodeError:
        return None

    self_info = data.get("Self") or {}
    dns_name = self_info.get("DNSName", "") or data.get("DNSName", "")
    cert_domains = data.get("CertDomains") or []
    ips = data.get("TailscaleIPs") or []

    if not dns_name or not cert_domains:
        return None

    return {
        "hostname": dns_name.rstrip("."),
        "ips": ips,
        "cert_domains": cert_domains,
    }


def generate_tailscale(cert_path, key_path, hostname: str) -> dict | None:
    """Obtain a Let's Encrypt certificate via Tailscale.

    Args:
        cert_path: Destination path for the certificate PEM file.
        key_path:  Destination path for the private key PEM file.
        hostname:  Tailscale hostname to request a certificate for.

    Returns:
        dict with keys: method, cert_path, key_path, hostnames, expires.
        Returns None on failure (non-zero exit, timeout, OS error, or missing files).
    """
    import subprocess

    cert_path = Path(cert_path)
    key_path = Path(key_path)

    cert_path.parent.mkdir(parents=True, exist_ok=True)
    key_path.parent.mkdir(parents=True, exist_ok=True)

    try:
        result = subprocess.run(
            [
                "tailscale",
                "cert",
                "--cert-file",
                str(cert_path),
                "--key-file",
                str(key_path),
                hostname,
            ],
            capture_output=True,
            text=True,
            timeout=30,
        )
    except (subprocess.TimeoutExpired, OSError):
        return None

    if result.returncode != 0:
        return None

    if not cert_path.exists() or not key_path.exists():
        return None

    key_path.chmod(0o600)

    info = get_cert_info(cert_path)
    if info is None:
        return None

    return {
        "method": "tailscale",
        "cert_path": str(cert_path),
        "key_path": str(key_path),
        "hostnames": info["hostnames"],
        "expires": info["expires"],
    }


def detect_mkcert() -> bool:
    """Return True if mkcert is available on PATH, False otherwise."""
    import shutil

    return shutil.which("mkcert") is not None


def generate_mkcert(
    cert_path,
    key_path,
    extra_hostnames: list[str] | None = None,
) -> dict | None:
    """Generate a locally-trusted certificate via mkcert.

    Args:
        cert_path: Destination path for the certificate PEM file.
        key_path:  Destination path for the private key PEM file.
        extra_hostnames: Additional hostnames to include in the certificate.

    Returns:
        dict with keys: method, cert_path, key_path, hostnames, expires.
        Returns None on failure (mkcert not found, non-zero exit, timeout, or missing files).
    """
    import subprocess

    cert_path = Path(cert_path)
    key_path = Path(key_path)

    cert_path.parent.mkdir(parents=True, exist_ok=True)
    key_path.parent.mkdir(parents=True, exist_ok=True)

    # Step 1: install the local CA
    try:
        result = subprocess.run(
            ["mkcert", "-install"],
            capture_output=True,
            text=True,
            timeout=30,
        )
    except (subprocess.TimeoutExpired, OSError):
        return None

    if result.returncode != 0:
        return None

    # Step 2: build deduplicated hostname list (preserving order)
    hostname = socket.gethostname()
    base_hostnames = [hostname, f"{hostname}.local", "localhost", "127.0.0.1", "::1"]
    if extra_hostnames:
        base_hostnames.extend(extra_hostnames)

    seen: set[str] = set()
    unique_hostnames: list[str] = []
    for h in base_hostnames:
        if h not in seen:
            seen.add(h)
            unique_hostnames.append(h)

    # Step 3: generate the certificate
    try:
        result = subprocess.run(
            [
                "mkcert",
                "-cert-file",
                str(cert_path),
                "-key-file",
                str(key_path),
                *unique_hostnames,
            ],
            capture_output=True,
            text=True,
            timeout=30,
        )
    except (subprocess.TimeoutExpired, OSError):
        return None

    if result.returncode != 0:
        return None

    if not cert_path.exists() or not key_path.exists():
        return None

    key_path.chmod(0o600)

    info = get_cert_info(cert_path)
    expires = info["expires"] if info else None

    return {
        "method": "mkcert",
        "cert_path": str(cert_path),
        "key_path": str(key_path),
        "hostnames": unique_hostnames,
        "expires": expires,
    }


def get_cert_info(cert_path) -> dict | None:
    """Inspect a PEM certificate and return metadata.

    Args:
        cert_path: Path to the PEM certificate file.

    Returns:
        dict with expires, not_before, hostnames (DNS names + IPs from SANs), serial.
        Returns None if the file is missing or cannot be parsed.
    """
    from cryptography import x509
    from cryptography.x509.extensions import ExtensionNotFound

    cert_path = Path(cert_path)

    try:
        pem_data = cert_path.read_bytes()
    except (FileNotFoundError, PermissionError, OSError):
        return None

    try:
        cert = x509.load_pem_x509_certificate(pem_data)
    except Exception:
        return None

    # Extract hostnames from SAN extension
    hostnames: list[str] = []
    try:
        san = cert.extensions.get_extension_for_class(x509.SubjectAlternativeName)
        for entry in san.value:
            if isinstance(entry, x509.DNSName):
                hostnames.append(entry.value)
            elif isinstance(entry, x509.IPAddress):
                hostnames.append(str(entry.value))
    except ExtensionNotFound:
        pass

    try:
        expires = cert.not_valid_after_utc  # type: ignore[attr-defined]
    except AttributeError:
        expires = cert.not_valid_after  # type: ignore[attr-defined]

    try:
        not_before = cert.not_valid_before_utc  # type: ignore[attr-defined]
    except AttributeError:
        not_before = cert.not_valid_before  # type: ignore[attr-defined]

    return {
        "expires": expires,
        "not_before": not_before,
        "hostnames": hostnames,
        "serial": cert.serial_number,
    }