"""OAuth2 Authentication implementation for httpx2.

Implements authorization code flow with PKCE and automatic token refresh.
"""

import base64
import hashlib
import logging
import secrets
import string
import time
from collections.abc import AsyncGenerator, Awaitable, Callable
from dataclasses import dataclass, field
from typing import Any, Protocol, get_args
from urllib.parse import quote, urlencode, urljoin, urlparse

import anyio
import httpx2
from mcp_types.version import is_version_at_least
from pydantic import BaseModel, Field, ValidationError

from mcp.client.auth.exceptions import OAuthFlowError, OAuthRegistrationError, OAuthTokenError
from mcp.client.auth.utils import (
    build_oauth_authorization_server_metadata_discovery_urls,
    build_protected_resource_metadata_discovery_urls,
    create_client_info_from_metadata_url,
    create_client_registration_request,
    create_oauth_metadata_request,
    credentials_match_issuer,
    extract_field_from_www_auth,
    extract_resource_metadata_from_www_auth,
    extract_scope_from_www_auth,
    get_client_metadata_scopes,
    handle_auth_metadata_response,
    handle_protected_resource_response,
    handle_registration_response,
    handle_token_response_scopes,
    is_valid_client_metadata_url,
    should_use_client_metadata_url,
    union_scopes,
    validate_authorization_response_iss,
    validate_metadata_issuer,
)
from mcp.shared.auth import (
    AuthorizationCodeResult,
    OAuthClientInformationFull,
    OAuthClientMetadata,
    OAuthMetadata,
    OAuthToken,
    ProtectedResourceMetadata,
    TokenEndpointAuthMethod,
)
from mcp.shared.auth_utils import (
    calculate_token_expiry,
    check_resource_allowed,
    resource_url_from_server_url,
)
from mcp.shared.inbound import MCP_PROTOCOL_VERSION_HEADER

logger = logging.getLogger(__name__)

# Methods a registered client's record may carry without a token request being an error,
# derived from the set the SDK is willing to request so the two cannot drift. `None`/"none"
# send no client secret. `private_key_jwt` sends none from here either: only
# `PrivateKeyJWTOAuthProvider` signs the assertion, and only in its client-credentials
# exchange, so its inherited refresh path must pass through here without raising - a refresh
# the server then rejects falls back to a fresh client-credentials exchange, which signs.
# Anything else is a method no client here can apply.
_KNOWN_TOKEN_ENDPOINT_AUTH_METHODS: tuple[str | None, ...] = (None, *get_args(TokenEndpointAuthMethod))

# Methods that authenticate the token request with the minted `client_secret`; a
# registration assigning one is only usable if the server issued that secret.
_SECRET_TOKEN_ENDPOINT_AUTH_METHODS = ("client_secret_post", "client_secret_basic")

# Methods a registration completed by the authorization-code flow can act on. That flow
# authenticates the token request with the minted client secret (or nothing); it holds no key
# to sign a `private_key_jwt` assertion, so a server assigning that method has registered a
# client this flow cannot use. `PrivateKeyJWTOAuthProvider` never registers dynamically.
_REGISTRATION_USABLE_TOKEN_ENDPOINT_AUTH_METHODS: tuple[str | None, ...] = tuple(
    method for method in _KNOWN_TOKEN_ENDPOINT_AUTH_METHODS if method != "private_key_jwt"
)


def check_registration_usable(client_info: OAuthClientInformationFull) -> None:
    """Confirm a registration this flow completed is one it can act on.

    RFC 7591 §3.2.1 lets the authorization server replace requested metadata and leaves it to
    the client to "check the values in the response to determine if the registration is
    sufficient for use". Two substitutions make the minted credentials unusable, and both are
    judged here - before the record is persisted or any interactive authorization begins -
    rather than surfacing later as an opaque failure at the token endpoint: a token-endpoint
    auth method the authorization-code flow cannot apply (one it does not implement, or
    `private_key_jwt`, whose assertion this flow has no key to sign), and a secret-based
    method the flow could apply but for which the server issued no `client_secret`.

    Raises:
        OAuthRegistrationError: The server registered the client with a
            `token_endpoint_auth_method` this flow cannot apply, or with a secret-based
            method but no `client_secret`.
    """
    method = client_info.token_endpoint_auth_method
    if method not in _REGISTRATION_USABLE_TOKEN_ENDPOINT_AUTH_METHODS:
        raise OAuthRegistrationError(
            f"Authorization server registered the client with unsupported token_endpoint_auth_method {method!r}"
        )
    if method in _SECRET_TOKEN_ENDPOINT_AUTH_METHODS and client_info.client_secret is None:
        raise OAuthRegistrationError(
            f"Authorization server registered the client for {method!r} but issued no client_secret"
        )


class PKCEParameters(BaseModel):
    """PKCE (Proof Key for Code Exchange) parameters."""

    code_verifier: str = Field(..., min_length=43, max_length=128)
    code_challenge: str = Field(..., min_length=43, max_length=128)

    @classmethod
    def generate(cls) -> "PKCEParameters":
        """Generate new PKCE parameters."""
        code_verifier = "".join(secrets.choice(string.ascii_letters + string.digits + "-._~") for _ in range(128))
        digest = hashlib.sha256(code_verifier.encode()).digest()
        code_challenge = base64.urlsafe_b64encode(digest).decode().rstrip("=")
        return cls(code_verifier=code_verifier, code_challenge=code_challenge)


class TokenStorage(Protocol):
    """Protocol for token storage implementations."""

    async def get_tokens(self) -> OAuthToken | None:
        """Get stored tokens."""
        ...

    async def set_tokens(self, tokens: OAuthToken) -> None:
        """Store tokens."""
        ...

    async def get_client_info(self) -> OAuthClientInformationFull | None:
        """Get stored client information."""
        ...

    async def set_client_info(self, client_info: OAuthClientInformationFull) -> None:
        """Store client information."""
        ...


@dataclass
class OAuthContext:
    """OAuth flow context."""

    server_url: str
    client_metadata: OAuthClientMetadata
    storage: TokenStorage
    redirect_handler: Callable[[str], Awaitable[None]] | None
    callback_handler: Callable[[], Awaitable[AuthorizationCodeResult]] | None
    client_metadata_url: str | None = None

    # Discovered metadata
    protected_resource_metadata: ProtectedResourceMetadata | None = None
    oauth_metadata: OAuthMetadata | None = None
    auth_server_url: str | None = None
    protocol_version: str | None = None

    # Client registration
    client_info: OAuthClientInformationFull | None = None

    # Token management
    current_tokens: OAuthToken | None = None
    token_expiry_time: float | None = None

    # State
    lock: anyio.Lock = field(default_factory=anyio.Lock)

    def get_authorization_base_url(self, server_url: str) -> str:
        """Extract base URL by removing path component."""
        parsed = urlparse(server_url)
        return f"{parsed.scheme}://{parsed.netloc}"

    def update_token_expiry(self, token: OAuthToken) -> None:
        """Update token expiry time using shared util function."""
        self.token_expiry_time = calculate_token_expiry(token.expires_in)

    def is_token_valid(self) -> bool:
        """Check if current token is valid."""
        return bool(
            self.current_tokens
            and self.current_tokens.access_token
            and (not self.token_expiry_time or time.time() <= self.token_expiry_time)
        )

    def can_refresh_token(self) -> bool:
        """Check if token can be refreshed."""
        return bool(self.current_tokens and self.current_tokens.refresh_token and self.client_info)

    def clear_tokens(self) -> None:
        """Clear current tokens."""
        self.current_tokens = None
        self.token_expiry_time = None

    def get_resource_url(self) -> str:
        """Get resource URL for RFC 8707.

        Uses PRM resource if it's a valid parent, otherwise uses canonical server URL.
        """
        resource = resource_url_from_server_url(self.server_url)

        # If PRM provides a resource that's a valid parent, use it
        if self.protected_resource_metadata and self.protected_resource_metadata.resource:
            prm_resource = str(self.protected_resource_metadata.resource)
            if check_resource_allowed(requested_resource=resource, configured_resource=prm_resource):
                resource = prm_resource

        return resource

    def should_include_resource_param(self, protocol_version: str | None = None) -> bool:
        """Determine if the resource parameter should be included in OAuth requests.

        Returns True if:
        - Protected resource metadata is available, OR
        - MCP-Protocol-Version header is 2025-06-18 or later
        """
        # If we have protected resource metadata, include the resource param
        if self.protected_resource_metadata is not None:
            return True

        # If no protocol version provided, don't include resource param
        if not protocol_version:
            return False

        return is_version_at_least(protocol_version, "2025-06-18")

    def prepare_token_auth(
        self, data: dict[str, str], headers: dict[str, str] | None = None
    ) -> tuple[dict[str, str], dict[str, str]]:
        """Prepare authentication for token requests.

        Args:
            data: The form data to send
            headers: Optional headers dict to update

        Returns:
            Tuple of (updated_data, updated_headers)

        Raises:
            OAuthTokenError: The client record carries a `token_endpoint_auth_method` this
                client does not know. A dynamic registration assigning an unusable method is
                rejected earlier, by `check_registration_usable`; this fires for a stored or
                pre-registered record that reaches a token request with such a method.
        """
        if headers is None:
            headers = {}  # pragma: no cover

        if not self.client_info:
            return data, headers

        auth_method = self.client_info.token_endpoint_auth_method

        if auth_method == "client_secret_basic" and self.client_info.client_secret:
            # URL-encode client ID and secret per RFC 6749 Section 2.3.1
            encoded_id = quote(self.client_info.client_id, safe="")
            encoded_secret = quote(self.client_info.client_secret, safe="")
            credentials = f"{encoded_id}:{encoded_secret}"
            encoded_credentials = base64.b64encode(credentials.encode()).decode()
            headers["Authorization"] = f"Basic {encoded_credentials}"
            # Don't include client_secret in body for basic auth
            data = {k: v for k, v in data.items() if k != "client_secret"}
        elif auth_method == "client_secret_post" and self.client_info.client_secret:
            # Include client_id and client_secret in request body (RFC 6749 §2.3.1)
            data["client_id"] = self.client_info.client_id
            data["client_secret"] = self.client_info.client_secret
        elif auth_method not in _KNOWN_TOKEN_ENDPOINT_AUTH_METHODS:
            raise OAuthTokenError(f"Registered client uses unsupported token_endpoint_auth_method {auth_method!r}")
        # For "none" (or absent), don't add any client_secret; "private_key_jwt" adds its
        # assertion in the provider that implements it, not here.

        return data, headers


class OAuthClientProvider(httpx2.Auth):
    """OAuth2 authentication for httpx2.

    Handles OAuth flow with automatic client registration and token storage.
    """

    requires_response_body = True

    def __init__(
        self,
        server_url: str,
        client_metadata: OAuthClientMetadata,
        storage: TokenStorage,
        redirect_handler: Callable[[str], Awaitable[None]] | None = None,
        callback_handler: Callable[[], Awaitable[AuthorizationCodeResult]] | None = None,
        client_metadata_url: str | None = None,
        validate_resource_url: Callable[[str, str | None], Awaitable[None]] | None = None,
    ):
        """Initialize OAuth2 authentication.

        Args:
            server_url: The MCP server URL.
            client_metadata: OAuth client metadata for registration.
            storage: Token storage implementation.
            redirect_handler: Handler for authorization redirects.
            callback_handler: Handler for authorization callbacks.
            client_metadata_url: URL-based client ID. When provided and the server
                advertises client_id_metadata_document_supported=True, this URL will be
                used as the client_id instead of performing dynamic client registration.
                Must be a valid HTTPS URL with a non-root pathname.
            validate_resource_url: Optional callback to override resource URL validation.
                Called with (server_url, prm_resource) where prm_resource is the resource
                from Protected Resource Metadata (or None if not present). If not provided,
                default validation rejects mismatched resources per RFC 8707.

        Raises:
            ValueError: If client_metadata_url is provided but not a valid HTTPS URL
                with a non-root pathname.
        """
        # Validate client_metadata_url if provided
        if client_metadata_url is not None and not is_valid_client_metadata_url(client_metadata_url):
            raise ValueError(
                f"client_metadata_url must be a valid HTTPS URL with a non-root pathname, got: {client_metadata_url}"
            )

        self.context = OAuthContext(
            server_url=server_url,
            client_metadata=client_metadata,
            storage=storage,
            redirect_handler=redirect_handler,
            callback_handler=callback_handler,
            client_metadata_url=client_metadata_url,
        )
        self._validate_resource_url_callback = validate_resource_url
        self._initialized = False

    async def _handle_protected_resource_response(self, response: httpx2.Response) -> bool:
        """Handle protected resource metadata discovery response.

        Per SEP-985, supports fallback when discovery fails at one URL.

        Returns:
            True if metadata was successfully discovered, False if we should try next URL
        """
        if response.status_code == 200:
            try:
                content = await response.aread()
                metadata = ProtectedResourceMetadata.model_validate_json(content)
                self.context.protected_resource_metadata = metadata
                if metadata.authorization_servers:  # pragma: no branch
                    self.context.auth_server_url = str(metadata.authorization_servers[0])
                return True

            except ValidationError:  # pragma: no cover
                # Invalid metadata - try next URL
                logger.warning(f"Invalid protected resource metadata at {response.request.url}")
                return False
        elif response.status_code == 404:  # pragma: no cover
            # Not found - try next URL in fallback chain
            logger.debug(f"Protected resource metadata not found at {response.request.url}, trying next URL")
            return False
        else:
            # Other error - fail immediately
            raise OAuthFlowError(
                f"Protected Resource Metadata request failed: {response.status_code}"
            )  # pragma: no cover

    async def _perform_authorization(self) -> httpx2.Request:
        """Perform the authorization flow."""
        auth_code, code_verifier = await self._perform_authorization_code_grant()
        token_request = await self._exchange_token_authorization_code(auth_code, code_verifier)
        return token_request

    async def _perform_authorization_code_grant(self) -> tuple[str, str]:
        """Perform the authorization redirect and get auth code."""
        if self.context.client_metadata.redirect_uris is None:
            raise OAuthFlowError("No redirect URIs provided for authorization code grant")  # pragma: no cover
        if not self.context.redirect_handler:
            raise OAuthFlowError("No redirect handler provided for authorization code grant")  # pragma: no cover
        if not self.context.callback_handler:
            raise OAuthFlowError("No callback handler provided for authorization code grant")  # pragma: no cover

        if self.context.oauth_metadata and self.context.oauth_metadata.authorization_endpoint:
            auth_endpoint = str(self.context.oauth_metadata.authorization_endpoint)
        else:
            auth_base_url = self.context.get_authorization_base_url(self.context.server_url)
            auth_endpoint = urljoin(auth_base_url, "/authorize")

        if not self.context.client_info:
            raise OAuthFlowError("No client info available for authorization")  # pragma: no cover

        # Generate PKCE parameters
        pkce_params = PKCEParameters.generate()
        state = secrets.token_urlsafe(32)

        auth_params = {
            "response_type": "code",
            "client_id": self.context.client_info.client_id,
            "redirect_uri": str(self.context.client_metadata.redirect_uris[0]),
            "state": state,
            "code_challenge": pkce_params.code_challenge,
            "code_challenge_method": "S256",
        }

        # Only include resource param if conditions are met
        if self.context.should_include_resource_param(self.context.protocol_version):
            auth_params["resource"] = self.context.get_resource_url()  # RFC 8707

        if self.context.client_metadata.scope:  # pragma: no branch
            auth_params["scope"] = self.context.client_metadata.scope

            # OIDC requires prompt=consent when offline_access is requested
            # https://openid.net/specs/openid-connect-core-1_0.html#OfflineAccess
            if "offline_access" in self.context.client_metadata.scope.split():
                auth_params["prompt"] = "consent"

        authorization_url = f"{auth_endpoint}?{urlencode(auth_params)}"
        await self.context.redirect_handler(authorization_url)

        # Wait for callback
        result = await self.context.callback_handler()

        if result.state is None or not secrets.compare_digest(result.state, state):
            raise OAuthFlowError(f"State parameter mismatch: {result.state} != {state}")

        # RFC 9207: validate the authorization-response issuer
        validate_authorization_response_iss(result.iss, self.context.oauth_metadata)

        if not result.code:
            raise OAuthFlowError("No authorization code received")

        # Return auth code and code verifier for token exchange
        return result.code, pkce_params.code_verifier

    def _get_token_endpoint(self) -> str:
        if self.context.oauth_metadata and self.context.oauth_metadata.token_endpoint:
            token_url = str(self.context.oauth_metadata.token_endpoint)
        else:
            auth_base_url = self.context.get_authorization_base_url(self.context.server_url)
            token_url = urljoin(auth_base_url, "/token")
        return token_url

    async def _exchange_token_authorization_code(self, auth_code: str, code_verifier: str) -> httpx2.Request:
        """Build token exchange request for authorization_code flow."""
        if self.context.client_metadata.redirect_uris is None:
            raise OAuthFlowError("No redirect URIs provided for authorization code grant")  # pragma: no cover
        if not self.context.client_info:
            raise OAuthFlowError("Missing client info")  # pragma: no cover

        token_url = self._get_token_endpoint()
        token_data: dict[str, Any] = {
            "grant_type": "authorization_code",
            "code": auth_code,
            "redirect_uri": str(self.context.client_metadata.redirect_uris[0]),
            "client_id": self.context.client_info.client_id,
            "code_verifier": code_verifier,
        }

        # Only include resource param if conditions are met
        if self.context.should_include_resource_param(self.context.protocol_version):
            token_data["resource"] = self.context.get_resource_url()  # RFC 8707

        # Prepare authentication based on preferred method
        headers = {"Content-Type": "application/x-www-form-urlencoded"}
        token_data, headers = self.context.prepare_token_auth(token_data, headers)

        return httpx2.Request("POST", token_url, data=token_data, headers=headers)

    async def _handle_token_response(self, response: httpx2.Response) -> None:
        """Handle token exchange response."""
        if response.status_code not in {200, 201}:
            body = await response.aread()
            body_text = body.decode("utf-8")
            raise OAuthTokenError(f"Token exchange failed ({response.status_code}): {body_text}")

        # Parse and validate response with scope validation
        token_response = await handle_token_response_scopes(response)

        # RFC 6749 §5.1: an omitted scope means the granted scope equals the requested
        # scope. Record it explicitly so the persisted token is self-describing — the
        # SEP-2350 step-up union reads it after a restart, when client_metadata.scope
        # has reverted to its constructor value.
        if token_response.scope is None:
            token_response.scope = self.context.client_metadata.scope

        # Store tokens in context
        self.context.current_tokens = token_response
        self.context.update_token_expiry(token_response)
        await self.context.storage.set_tokens(token_response)

    async def _refresh_token(self) -> httpx2.Request:
        """Build token refresh request."""
        if not self.context.current_tokens or not self.context.current_tokens.refresh_token:
            raise OAuthTokenError("No refresh token available")  # pragma: no cover

        if not self.context.client_info or not self.context.client_info.client_id:
            raise OAuthTokenError("No client info available")  # pragma: no cover

        if self.context.oauth_metadata and self.context.oauth_metadata.token_endpoint:
            token_url = str(self.context.oauth_metadata.token_endpoint)
        else:
            auth_base_url = self.context.get_authorization_base_url(self.context.server_url)
            token_url = urljoin(auth_base_url, "/token")

        refresh_data: dict[str, str] = {
            "grant_type": "refresh_token",
            "refresh_token": self.context.current_tokens.refresh_token,
            "client_id": self.context.client_info.client_id,
        }

        # Only include resource param if conditions are met
        if self.context.should_include_resource_param(self.context.protocol_version):
            refresh_data["resource"] = self.context.get_resource_url()  # RFC 8707

        # Prepare authentication based on preferred method
        headers = {"Content-Type": "application/x-www-form-urlencoded"}
        refresh_data, headers = self.context.prepare_token_auth(refresh_data, headers)

        return httpx2.Request("POST", token_url, data=refresh_data, headers=headers)

    async def _handle_refresh_response(self, response: httpx2.Response) -> bool:
        """Handle token refresh response. Returns True if successful."""
        if response.status_code != 200:
            logger.warning(f"Token refresh failed: {response.status_code}")
            self.context.clear_tokens()
            return False

        try:
            content = await response.aread()
            token_response = OAuthToken.model_validate_json(content)

            # RFC 6749 §6: a refresh response may omit scope (unchanged) and refresh_token
            # (the AS does not rotate). Carry both forward so the persisted token stays
            # self-describing for the SEP-2350 step-up union and the next expiry can
            # still refresh instead of forcing a full re-authorization.
            prior = self.context.current_tokens
            if token_response.scope is None and prior is not None:
                token_response.scope = prior.scope
            if token_response.refresh_token is None and prior is not None:
                token_response.refresh_token = prior.refresh_token

            self.context.current_tokens = token_response
            self.context.update_token_expiry(token_response)
            await self.context.storage.set_tokens(token_response)

            return True
        except ValidationError:  # pragma: no cover
            logger.exception("Invalid refresh response")
            self.context.clear_tokens()
            return False

    async def _initialize(self) -> None:
        """Load stored tokens and client info."""
        self.context.current_tokens = await self.context.storage.get_tokens()
        self.context.client_info = await self.context.storage.get_client_info()
        self._initialized = True

    def _add_auth_header(self, request: httpx2.Request) -> None:
        """Add authorization header to request if we have valid tokens."""
        if self.context.current_tokens and self.context.current_tokens.access_token:  # pragma: no branch
            request.headers["Authorization"] = f"Bearer {self.context.current_tokens.access_token}"

    async def _handle_oauth_metadata_response(self, response: httpx2.Response) -> None:
        content = await response.aread()
        metadata = OAuthMetadata.model_validate_json(content)
        self.context.oauth_metadata = metadata

    async def _validate_resource_match(self, prm: ProtectedResourceMetadata) -> None:
        """Validate that PRM resource matches the server URL per RFC 8707."""
        prm_resource = str(prm.resource) if prm.resource else None

        if self._validate_resource_url_callback is not None:
            await self._validate_resource_url_callback(self.context.server_url, prm_resource)
            return

        if not prm_resource:
            return  # pragma: no cover
        default_resource = resource_url_from_server_url(self.context.server_url)
        if not check_resource_allowed(requested_resource=default_resource, configured_resource=prm_resource):
            raise OAuthFlowError(f"Protected resource {prm_resource} does not match expected {default_resource}")

    async def async_auth_flow(self, request: httpx2.Request) -> AsyncGenerator[httpx2.Request, httpx2.Response]:
        """httpx2 auth flow integration."""
        async with self.context.lock:
            if not self._initialized:
                await self._initialize()

            # Capture protocol version from request headers
            self.context.protocol_version = request.headers.get(MCP_PROTOCOL_VERSION_HEADER)

            if not self.context.is_token_valid() and self.context.can_refresh_token():
                # Try to refresh token
                refresh_request = await self._refresh_token()
                refresh_response = yield refresh_request

                if not await self._handle_refresh_response(refresh_response):
                    # Refresh failed, need full re-authentication
                    self._initialized = False

            if self.context.is_token_valid():
                self._add_auth_header(request)

            response = yield request

            if response.status_code == 401:
                # Perform full OAuth flow
                try:
                    # OAuth flow must be inline due to generator constraints
                    www_auth_resource_metadata_url = extract_resource_metadata_from_www_auth(response)

                    # Step 1: Discover protected resource metadata (SEP-985 with fallback support)
                    prm_discovery_urls = build_protected_resource_metadata_discovery_urls(
                        www_auth_resource_metadata_url, self.context.server_url
                    )

                    for url in prm_discovery_urls:  # pragma: no branch
                        discovery_request = create_oauth_metadata_request(url)

                        discovery_response = yield discovery_request  # sending request

                        prm = await handle_protected_resource_response(discovery_response)
                        if prm:
                            # Validate PRM resource matches server URL (RFC 8707)
                            await self._validate_resource_match(prm)
                            self.context.protected_resource_metadata = prm

                            # todo: try all authorization_servers to find the OASM
                            assert (
                                len(prm.authorization_servers) > 0
                            )  # this is always true as authorization_servers has a min length of 1

                            self.context.auth_server_url = str(prm.authorization_servers[0])
                            break
                        else:
                            logger.debug(f"Protected resource metadata discovery failed: {url}")

                    # SEP-2352: stored credentials are bound to the issuer that registered them.
                    # If the authorization server changed, drop them (and the old tokens) so the
                    # flow re-registers instead of presenting another server's credentials.
                    if (
                        self.context.client_info is not None
                        and self.context.auth_server_url is not None
                        and not credentials_match_issuer(
                            self.context.client_info, self.context.auth_server_url, self.context.client_metadata_url
                        )
                    ):
                        logger.debug("Authorization server changed; discarding bound credentials and re-registering")
                        self.context.client_info = None
                        self.context.clear_tokens()
                        # Any cached AS metadata is for the old server; drop it so a failed
                        # rediscovery cannot leak the old registration/token endpoints into Step 4.
                        self.context.oauth_metadata = None

                    asm_discovery_urls = build_oauth_authorization_server_metadata_discovery_urls(
                        self.context.auth_server_url, self.context.server_url
                    )

                    # Step 2: Discover OAuth Authorization Server Metadata (OASM) (with fallback for legacy servers)
                    for url in asm_discovery_urls:  # pragma: no branch
                        oauth_metadata_request = create_oauth_metadata_request(url)
                        oauth_metadata_response = yield oauth_metadata_request

                        ok, asm = await handle_auth_metadata_response(oauth_metadata_response)
                        if not ok:
                            break
                        if ok and asm:
                            # SEP-2468: metadata issuer must match the discovery issuer
                            if self.context.auth_server_url is not None:
                                validate_metadata_issuer(asm, self.context.auth_server_url)
                            self.context.oauth_metadata = asm
                            break
                        else:
                            logger.debug(f"OAuth metadata discovery failed: {url}")

                    # SEP-2352: on the legacy no-PRM path the issuer is only known after ASM
                    # discovery, so re-evaluate the binding here using the discovered metadata
                    # issuer (mirroring the bound_issuer fallback in Step 4).
                    if (
                        self.context.client_info is not None
                        and self.context.auth_server_url is None
                        and self.context.oauth_metadata is not None
                        and not credentials_match_issuer(
                            self.context.client_info,
                            str(self.context.oauth_metadata.issuer),
                            self.context.client_metadata_url,
                        )
                    ):
                        logger.debug("Authorization server changed; discarding bound credentials and re-registering")
                        self.context.client_info = None
                        self.context.clear_tokens()

                    # Step 3: Apply scope selection strategy
                    self.context.client_metadata.scope = get_client_metadata_scopes(
                        extract_scope_from_www_auth(response),
                        self.context.protected_resource_metadata,
                        self.context.oauth_metadata,
                        self.context.client_metadata.grant_types,
                    )

                    # Step 4: Register client or use URL-based client ID (CIMD)
                    if not self.context.client_info:
                        # SEP-2352: the issuer to bind these credentials to, when known.
                        discovered_issuer: str | None = None
                        if self.context.oauth_metadata is not None:
                            discovered_issuer = self.context.auth_server_url or str(self.context.oauth_metadata.issuer)

                        if should_use_client_metadata_url(
                            self.context.oauth_metadata, self.context.client_metadata_url
                        ):
                            # Use URL-based client ID (CIMD). CIMD records are portable across
                            # authorization servers, so the issuer stamp is informational.
                            logger.debug(f"Using URL-based client ID (CIMD): {self.context.client_metadata_url}")
                            client_information = create_client_info_from_metadata_url(
                                self.context.client_metadata_url,  # type: ignore[arg-type]
                                redirect_uris=self.context.client_metadata.redirect_uris,
                            )
                            client_information.issuer = discovered_issuer
                            self.context.client_info = client_information
                            await self.context.storage.set_client_info(client_information)
                        else:
                            # Fallback to Dynamic Client Registration
                            fallback_base = self.context.get_authorization_base_url(self.context.server_url)
                            registration_request = create_client_registration_request(
                                self.context.oauth_metadata, self.context.client_metadata, fallback_base
                            )
                            registration_response = yield registration_request
                            client_information = await handle_registration_response(registration_response)
                            check_registration_usable(client_information)
                            # Only record the issuer when the registration above actually targeted
                            # the discovered AS — either via its published registration_endpoint,
                            # or because the resource-origin /register fallback is on the issuer's
                            # own host (legacy same-origin embedded AS). Otherwise the fallback hit
                            # a different server and recording a binding to the PRM-advertised AS
                            # would persist a binding that was never established.
                            if (
                                self.context.oauth_metadata is not None
                                and discovered_issuer is not None
                                and (
                                    self.context.oauth_metadata.registration_endpoint is not None
                                    or self.context.get_authorization_base_url(discovered_issuer) == fallback_base
                                )
                            ):
                                client_information.issuer = discovered_issuer
                            self.context.client_info = client_information
                            await self.context.storage.set_client_info(client_information)

                    # Step 5: Perform authorization and complete token exchange
                    token_response = yield await self._perform_authorization()
                    await self._handle_token_response(token_response)
                except Exception:
                    logger.exception("OAuth flow error")
                    raise

                # Retry with new tokens
                self._add_auth_header(request)
                yield request
            elif response.status_code == 403:
                # Step 1: Extract error field from WWW-Authenticate header
                error = extract_field_from_www_auth(response, "error")

                # Step 2: Check if we need to step-up authorization
                if error == "insufficient_scope":  # pragma: no branch
                    try:
                        # Step 2a: Union previously requested scopes with the newly challenged
                        # scopes (SEP-2350) so escalating one operation keeps the others' grants.
                        # Fold in the stored token's scope too: on a restart the token is reloaded
                        # but client_metadata.scope is not, so it would otherwise be the only basis.
                        challenged_scope = get_client_metadata_scopes(
                            extract_scope_from_www_auth(response),
                            self.context.protected_resource_metadata,
                            self.context.oauth_metadata,
                            self.context.client_metadata.grant_types,
                        )
                        granted_scope = self.context.current_tokens.scope if self.context.current_tokens else None
                        prior_scope = union_scopes(self.context.client_metadata.scope, granted_scope)
                        self.context.client_metadata.scope = union_scopes(prior_scope, challenged_scope)

                        # Step 2b: Perform (re-)authorization and token exchange
                        token_response = yield await self._perform_authorization()
                        await self._handle_token_response(token_response)
                    except Exception:  # pragma: no cover
                        logger.exception("OAuth flow error")
                        raise

                # Retry with new tokens
                self._add_auth_header(request)
                yield request
