arize-phoenix 11.23.1__py3-none-any.whl → 12.28.1__py3-none-any.whl

phoenix/server/ldap.py

@@ -0,0 +1,1449 @@
+"""LDAP authentication for Phoenix.
+
+Provides LDAP/Active Directory authentication following RFC 4510-4519 standards.
+
+TLS Connection Modes:
+    LDAP supports three connection security modes:
+
+    1. LDAPS (LDAP over TLS, port 636):
+        - TLS established at TCP connection layer (like HTTPS)
+        - Server created with use_ssl=True
+        - Bind credentials encrypted from the start
+        - No protocol-level upgrade needed
+
+    2. STARTTLS (Upgrade to TLS, port 389):
+        - Connection starts as plaintext on standard LDAP port
+        - Client sends Extended Request (OID 1.3.6.1.4.1.1466.20037) to upgrade
+        - Server upgrades connection to TLS
+        - All subsequent data (including bind) encrypted
+        - CRITICAL: Must call start_tls() BEFORE sending credentials
+
+    3. Plaintext (No encryption, testing only):
+        - All data transmitted unencrypted
+        - Not recommended for production
+
+Advanced TLS Configuration:
+    Phoenix supports enterprise TLS requirements via optional configuration:
+
+    - Custom CA Certificates (tls_ca_cert_file):
+        For LDAP servers using private/internal certificate authorities
+        not present in the system's default trust store.
+
+    - Client Certificates (tls_client_cert_file, tls_client_key_file):
+        For mutual TLS (mTLS) authentication where the LDAP server
+        requires client certificate validation.
+
+Security Considerations:
+    This module implements multiple layers of defense against LDAP-specific attacks:
+
+    - Anonymous Bind Prevention (RFC 4513 §5.1.2):
+        Empty passwords are rejected before any LDAP operation. Many LDAP servers
+        treat empty-password binds as "unauthenticated" (anonymous), which would
+        allow attackers to bypass authentication entirely.
+
+    - LDAP Injection Prevention (RFC 4515):
+        All user input is escaped before insertion into LDAP filters using
+        escape_filter_chars(). This prevents filter manipulation attacks like
+        username="*" or "admin)(uid=*".
+
+    - Referral Following Disabled:
+        ldap3 defaults to auto_referrals=True, which follows LDAP referrals to
+        ANY server and sends bind credentials automatically. An attacker who can
+        inject a referral response could steal service account credentials.
+        Phoenix disables this (auto_referrals=False) and relies on explicit
+        multi-server configuration for high availability instead.
+
+    - Timing Attack Mitigation:
+        When a user is not found, a dummy bind is performed to equalize response
+        times with the "wrong password" case, preventing username enumeration.
+
+    - Exception Sanitization:
+        LDAP exception messages may contain sensitive information (server IPs,
+        DNs, configuration details). Only the exception type is logged.
+
+Implementation Notes:
+    The ldap3 library requires explicit handling of STARTTLS via:
+        - AUTO_BIND_TLS_BEFORE_BIND constant for automatic bind flows
+        - Manual start_tls() call for explicit bind flows
+
+    Using auto_bind=True (AUTO_BIND_NO_TLS) with STARTTLS configuration
+    will transmit credentials in PLAINTEXT despite TLS being "enabled".
+    This is a critical security vulnerability that this module guards against.
+
+Thread Safety Note:
+    This implementation uses ldap3's default SYNC strategy (not SAFE_SYNC) because
+    Connection objects are created fresh for each authentication request and never
+    shared between threads. The SAFE_SYNC strategy would only be required if we
+    introduced connection pooling or reused Connection objects across requests.
+    Server objects ARE thread-safe (ldap3 uses internal locking for message IDs).
+
+    Note: ldap3's "ASYNC" strategy uses OS threads, NOT Python async/await coroutines.
+    The library has no native asyncio support—all strategies perform blocking socket I/O.
+    We therefore run ldap3 in a thread pool via anyio.to_thread.run_sync() to avoid
+    blocking the FastAPI event loop (see authenticate() docstring for details).
+
+Known Limitations:
+    - No connection pooling: Each authentication creates fresh connections.
+      For very high-volume deployments (>100 auth/sec), consider adding ldap3
+      connection pooling or an external LDAP proxy (e.g., HAProxy).
+
+    - No pagination for group searches: POSIX mode group searches may be
+      truncated if the directory contains >1000 matching groups per search base.
+      Most deployments won't hit this limit.
+
+    - No nested group resolution: Active Directory nested groups (group-in-group)
+      require recursive memberOf queries or LDAP_MATCHING_RULE_IN_CHAIN (OID
+      1.2.840.113556.1.4.1941). Currently only direct group memberships are
+      resolved. Configure flattened groups or use AD's tokenGroups attribute
+      if nested resolution is required.
+
+See Also:
+    _create_servers(): Server-level TLS configuration (use_ssl, tls)
+    _establish_connection(): Connection-level TLS upgrade (AUTO_BIND modes)
+    _verify_user_password(): Manual TLS upgrade sequencing
+"""
+
+from __future__ import annotations
+
+import logging
+import random
+import ssl
+from hashlib import md5
+from secrets import token_hex
+from typing import Any, Final, Literal, NamedTuple, cast, overload
+
+import anyio
+from anyio import CapacityLimiter
+from ldap3 import (
+    AUTO_BIND_DEFAULT,
+    AUTO_BIND_NO_TLS,
+    AUTO_BIND_NONE,
+    AUTO_BIND_TLS_BEFORE_BIND,
+    NONE,
+    SUBTREE,
+    Connection,
+    Entry,
+    Server,
+    Tls,
+)
+from ldap3.core.exceptions import LDAPException, LDAPInvalidCredentialsResult, LDAPInvalidDnError
+from ldap3.core.results import RESULT_SIZE_LIMIT_EXCEEDED
+from ldap3.utils.conv import escape_filter_chars
+from ldap3.utils.dn import parse_dn
+
+from phoenix.config import AssignableUserRoleName, LDAPConfig
+
+logger = logging.getLogger(__name__)
+
+# Limit concurrent LDAP operations to prevent thread pool exhaustion.
+# Each LDAP authentication spawns a thread (ldap3 is synchronous-only). This
+# limit acts as a safety valve against credential stuffing attacks or runaway
+# retry loops, not as a throughput target. 10 concurrent operations is more
+# than sufficient for typical Phoenix deployments.
+_LDAP_CONCURRENCY_LIMIT: Final[int] = 10
+_ldap_limiter: CapacityLimiter | None = None
+
+
+def _get_ldap_limiter() -> CapacityLimiter:
+    """Get or create the LDAP concurrency limiter (lazy initialization).
+
+    Lazy initialization is required because CapacityLimiter must be created
+    within an async context (it uses the current event loop). Creating it at
+    module load time would fail since there's no event loop yet.
+    """
+    global _ldap_limiter
+    if _ldap_limiter is None:
+        _ldap_limiter = CapacityLimiter(_LDAP_CONCURRENCY_LIMIT)
+    return _ldap_limiter
+
+
+def canonicalize_dn(dn: str) -> str | None:
+    r"""Canonicalize a Distinguished Name per RFC 4514.
+
+    This function normalizes DNs to a canonical form for case-insensitive
+    comparison and storage. It handles:
+    - Case normalization (attribute types and values lowercased)
+    - Whitespace normalization (stripped around = and ,)
+    - Multi-valued RDN ordering (sorted alphabetically for deterministic output)
+    - Escaped character preservation (maintains \, \+ etc.)
+    - Hex encoding normalization (decoded to canonical form)
+
+    RFC 4514 states that DNs are case-insensitive for comparison, but leaves
+    the canonical form implementation-defined. This implementation ensures that
+    semantically equivalent DNs (e.g., "cn=John" vs "CN=john") map to the same
+    canonical string, preventing duplicate database entries.
+
+    Args:
+        dn: LDAP Distinguished Name to canonicalize
+
+    Returns:
+        str: Canonical lowercase DN with normalized whitespace and sorted RDN components.
+        None: If DN parsing fails. Callers should handle this explicitly to avoid
+              inconsistent matching behavior.
+
+    Examples:
+        >>> canonicalize_dn("cn=John,ou=Users,dc=Example,dc=com")
+        'cn=john,ou=users,dc=example,dc=com'
+
+        >>> canonicalize_dn("CN=john+EMAIL=john@corp.com,OU=users,DC=example,DC=com")
+        'cn=john+email=john@corp.com,ou=users,dc=example,dc=com'
+
+        >>> canonicalize_dn("email=john@corp.com+cn=John,ou=Users,dc=Example,dc=com")
+        'cn=john+email=john@corp.com,ou=users,dc=example,dc=com'  # Sorted
+
+        >>> canonicalize_dn("invalid dn syntax")
+        None
+
+    References:
+        RFC 4514 Section 4: String representation of DNs are case-insensitive
+        ldap3 parse_dn(): Validates syntax and decomposes into components
+    """
+    # Handle empty DN (root DSE) - this is a valid DN per RFC 4514
+    if not dn.strip():
+        return ""
+
+    try:
+        # Parse DN with escaping and whitespace stripping
+        components = parse_dn(dn, escape=True, strip=True)
+    except LDAPInvalidDnError:
+        # Return None instead of falling back to simple lowercase.
+        # This prevents inconsistent canonicalization where the same DN
+        # could have different canonical forms depending on parser behavior.
+        # Callers must handle None explicitly (typically by skipping the DN).
+        return None
+
+    # Build canonical DN
+    canonical_parts = []
+    current_rdn_components = []
+
+    for attr_type, attr_value, separator in components:
+        # Normalize attribute type and value to lowercase
+        normalized_component = (attr_type.lower(), attr_value.lower())
+        current_rdn_components.append(normalized_component)
+
+        # When we hit a comma (or end), we've completed an RDN
+        if separator == "," or separator == "":
+            # Sort multi-valued RDN components for deterministic output
+            # Example: "email=x+cn=y" and "cn=y+email=x" both become "cn=y+email=x"
+            # Sorts by (type, value) tuple to handle rare cases of duplicate attribute types
+            current_rdn_components.sort()
+
+            # Format the RDN
+            rdn_str = "+".join(f"{attr}={value}" for attr, value in current_rdn_components)
+            canonical_parts.append(rdn_str)
+
+            # Reset for next RDN
+            current_rdn_components = []
+
+    return ",".join(canonical_parts)
+
+
+# Unicode marker for identifying LDAP users in oauth2_client_id column.
+# U+E000 from Private Use Area - guaranteed never to be assigned by Unicode Standard.
+#
+# Design Context:
+#   Phoenix's user table was originally designed for OAuth2 providers, using
+#   oauth2_client_id to identify the authentication source (e.g., "google",
+#   "github"). LDAP users need a distinct marker to differentiate them from
+#   OAuth users without requiring a database schema migration.
+#
+# The "(stopgap)" Suffix:
+#   Indicates this is a temporary solution. A future schema change should add
+#   a dedicated identity_provider column (enum: "local", "ldap", "oauth2", etc.)
+#   with oauth2_client_id nullable only for OAuth users. This marker enables
+#   LDAP support without blocking on that migration.
+#
+# Why U+E000?
+#   Private Use Area characters cannot appear in legitimate OAuth client IDs,
+#   ensuring no collision with real OAuth providers. The marker is also
+#   unlikely to be accidentally typed or injected.
+LDAP_CLIENT_ID_MARKER: Final[str] = "\ue000LDAP(stopgap)"
+
+
+def is_ldap_user(oauth2_client_id: str | None) -> bool:
+    """Check if an oauth2_client_id indicates an LDAP user.
+
+    This function checks for the LDAP_CLIENT_ID_MARKER prefix to distinguish
+    LDAP-authenticated users from OAuth2-authenticated users. Used throughout
+    the codebase to apply LDAP-specific logic (e.g., re-authentication flows,
+    password change handling).
+
+    Args:
+        oauth2_client_id: The OAuth2 client ID to check (can be None)
+
+    Returns:
+        True if the client ID indicates an LDAP user, False otherwise
+
+    Example:
+        >>> is_ldap_user("\\ue000LDAP(stopgap):user-unique-id")
+        True
+        >>> is_ldap_user("google-oauth2|12345")
+        False
+        >>> is_ldap_user(None)
+        False
+    """
+    return bool(oauth2_client_id and oauth2_client_id.startswith(LDAP_CLIENT_ID_MARKER))
+
+
+# Marker for null email values in the database.
+#
+# When LDAP directories don't have email attributes, Phoenix generates a
+# deterministic marker to satisfy the database's NOT NULL constraint. This
+# marker uses a Private Use Area (PUA) Unicode character to ensure it cannot
+# collide with any real email address.
+#
+# Format: "\ue000NULL(stopgap)" + md5(unique_id)
+#   - \uE000: PUA character (guaranteed never assigned by Unicode Standard)
+#   - NULL: Human-readable indicator that email is absent
+#   - md5(unique_id): Deterministic hash for uniqueness (32 hex chars)
+#
+# Example: "\ue000NULL(stopgap)7f3d2a1b9c8e4f5da2b6c903e1f47d8b"
+#
+# Design Context:
+#   This is a temporary bridge solution. The eventual solution is to make the
+#   email column nullable in the database schema. Until then, this marker
+#   enables LDAP authentication for directories without email attributes.
+#
+# Security Note:
+#   MD5 is used for deterministic uniqueness, NOT cryptographic security.
+#   The hash ensures the same unique_id always produces the same marker,
+#   preventing race conditions on concurrent logins.
+NULL_EMAIL_MARKER_PREFIX: Final[str] = "\ue000NULL(stopgap)"
+
+
+def generate_null_email_marker(unique_id: str) -> str:
+    """Generate a deterministic null email marker from a unique_id.
+
+    This function creates a marker for LDAP users whose directories don't
+    have email attributes. The marker satisfies the database's NOT NULL
+    constraint while being programmatically distinguishable from real emails.
+
+    The marker is deterministic: the same unique_id always produces the same
+    marker. This prevents race conditions when the same user logs in
+    concurrently from multiple sessions.
+
+    Args:
+        unique_id: The LDAP unique identifier (objectGUID, entryUUID, etc.)
+                   Must be non-empty.
+
+    Returns:
+        A null email marker in format: "\\ue000NULL(stopgap){md5_hash}"
+
+    Raises:
+        ValueError: If unique_id is empty or None.
+
+    Example:
+        >>> generate_null_email_marker("550E8400-E29B-41D4-A716-446655440000")
+        '\\ue000NULL(stopgap)7f3d2a1b9c8e4f5da2b6c903e1f47d8b'
+    """
+    if not unique_id:
+        raise ValueError("unique_id is required to generate null email marker")
+
+    # Normalize to lowercase for consistent hashing (UUIDs are case-insensitive)
+    normalized = unique_id.lower()
+    return f"{NULL_EMAIL_MARKER_PREFIX}{md5(normalized.encode()).hexdigest()}"
+
+
+def is_null_email_marker(email: str) -> bool:
+    """Check if an email value is a null email marker.
+
+    This function identifies placeholder values that were generated for LDAP
+    users whose directories don't have email attributes. Used to:
+    - Hide placeholder emails in the UI
+    - Skip email operations (welcome emails, password reset)
+    - Validate that users aren't trying to log in with marker values
+
+    Args:
+        email: The email value to check
+
+    Returns:
+        True if the value is a null email marker, False otherwise.
+
+    Example:
+        >>> is_null_email_marker("\\ue000NULL(stopgap)7f3d2a1b9c8e4f5da2b6c903e1f47d8b")
+        True
+        >>> is_null_email_marker("alice@example.com")
+        False
+    """
+    return email.startswith(NULL_EMAIL_MARKER_PREFIX)
+
+
+class LDAPUserInfo(NamedTuple):
+    """Authenticated LDAP user information.
+
+    Attributes:
+        email: User's email address, or None if PHOENIX_LDAP_ATTR_EMAIL is "null".
+               When None, a null email marker will be generated from unique_id.
+        display_name: User's display name for UI
+        groups: Tuple of group DNs the user belongs to (immutable)
+        user_dn: User's Distinguished Name (for audit/logging, NOT used for identity matching)
+        ldap_username: Username used to authenticate
+        role: Phoenix role mapped from LDAP groups
+        unique_id: Immutable identifier (objectGUID/entryUUID). Required when email is None.
+    """
+
+    email: str | None
+    display_name: str
+    groups: tuple[str, ...]
+    user_dn: str
+    ldap_username: str
+    role: str
+    unique_id: str | None = None  # objectGUID (AD), entryUUID (OpenLDAP) if configured
+
+
+class LDAPAuthenticator:
+    """Handles LDAP authentication and user attribute retrieval.
+
+    Supports both Active Directory and OpenLDAP:
+    - Active Directory: Uses memberOf attribute for group membership
+    - OpenLDAP/POSIX: Uses group search with member attribute
+    - Multi-server failover for high availability
+    - TLS/LDAPS with certificate validation (RFC 4513)
+    - Group-based role mapping with wildcard support
+    """
+
+    # Maximum credential lengths to prevent DoS via oversized inputs.
+    # These are generous limits - real usernames/passwords are much shorter.
+    _MAX_USERNAME_LENGTH: Final[int] = 256
+    _MAX_PASSWORD_LENGTH: Final[int] = 1024
+
+    def __init__(self, config: LDAPConfig):
+        """Initialize LDAP authenticator with configuration.
+
+        Args:
+            config: LDAP configuration including servers, search bases, and mappings
+        """
+        self.config = config
+        self.servers = self._create_servers()
+
+    def _create_servers(self) -> list[Server]:
+        """Create ldap3 Server objects for all configured hosts.
+
+        TLS Configuration Modes:
+            Phoenix supports three LDAP connection modes via tls_mode:
+
+            1. LDAPS (tls_mode="ldaps", port 636):
+                - Server: use_ssl=True, tls=<Tls config>
+                - TLS established at TCP connection layer (like HTTPS)
+                - Bind credentials encrypted from the start
+                - No start_tls() call needed
+
+            2. STARTTLS (tls_mode="starttls", port 389):
+                - Server: use_ssl=False, tls=<Tls config>
+                - Connection starts plaintext, upgraded to TLS via start_tls()
+                - Bind credentials encrypted ONLY after start_tls() completes
+                - CRITICAL: Must call start_tls() before bind (see _establish_connection)
+
+            3. Plaintext (tls_mode="none", testing only):
+                - Server: use_ssl=False, tls=None
+                - All data transmitted unencrypted
+                - NOT recommended for production
+
+        Key ldap3 Parameters:
+            use_ssl: Enable TLS at connection layer (True for LDAPS only)
+            tls: TLS configuration object (cert validation, certificates, etc.)
+                - Set for both LDAPS and STARTTLS (start_tls() uses this config)
+                - None for plaintext mode
+                - Supports advanced options:
+                    * Custom CA certificates (ca_certs_file)
+                    * Client certificates for mutual TLS
+                      (local_certificate_file, local_private_key_file)
+
+        Returns:
+            list[Server]: Server objects for all configured hosts (supports failover).
+        """
+        tls_config = None
+        use_tls = self.config.tls_mode != "none"
+        if use_tls:
+            # Configure TLS with certificate validation and optional advanced settings
+            tls_kwargs: dict[str, Any] = {
+                "validate": ssl.CERT_REQUIRED if self.config.tls_verify else ssl.CERT_NONE
+            }
+
+            # Custom CA certificate for private/internal CAs
+            if self.config.tls_ca_cert_file:
+                tls_kwargs["ca_certs_file"] = self.config.tls_ca_cert_file
+
+            # Client certificate for mutual TLS
+            if self.config.tls_client_cert_file and self.config.tls_client_key_file:
+                tls_kwargs["local_certificate_file"] = self.config.tls_client_cert_file
+                tls_kwargs["local_private_key_file"] = self.config.tls_client_key_file
+
+            tls_config = Tls(**tls_kwargs)
+
+        servers = []
+        for host in self.config.hosts:
+            server = Server(
+                host,
+                port=self.config.port,
+                use_ssl=(self.config.tls_mode == "ldaps"),
+                tls=tls_config,
+                connect_timeout=10,
+                get_info=NONE,  # Don't fetch schema/DSA info we don't use
+            )
+            servers.append(server)
+
+        return servers
+
+    def _establish_connection(self, server: Server) -> Connection:
+        """Establish a connection to the LDAP server.
+
+        Connection Flow by TLS Mode:
+            STARTTLS Mode (tls_mode="starttls"):
+                1. Open plaintext TCP connection (port 389)
+                2. Send Extended Request to upgrade to TLS
+                3. Perform TLS handshake
+                4. Send bind credentials (now encrypted)
+
+                Implementation: Use AUTO_BIND_TLS_BEFORE_BIND to ensure step 2-3
+                happen before step 4.
+
+            LDAPS Mode (tls_mode="ldaps"):
+                1. Establish TLS connection (port 636)
+                2. Send bind credentials (already encrypted)
+
+                Implementation: Use AUTO_BIND_NO_TLS (TLS already active from Server)
+
+            Plaintext Mode (tls_mode="none"):
+                1. Open plaintext TCP connection (port 389)
+                2. Send bind credentials (unencrypted)
+
+                Implementation: Use AUTO_BIND_NO_TLS (no TLS to upgrade)
+
+        ldap3 auto_bind Modes:
+            AUTO_BIND_TLS_BEFORE_BIND: Call start_tls(), then bind
+                - Required for STARTTLS to encrypt credentials
+            AUTO_BIND_NO_TLS: Bind immediately without calling start_tls()
+                - Correct for LDAPS (TLS already active via use_ssl=True)
+                - Correct for plaintext (no TLS desired)
+
+        Security Note:
+            For STARTTLS, using auto_bind=True (or AUTO_BIND_NO_TLS) would
+            transmit bind credentials in PLAINTEXT before upgrading to TLS.
+            This is a critical security vulnerability.
+
+        Bind Types:
+            Service account: Uses config.bind_dn and config.bind_password
+            Anonymous: No credentials (for servers allowing anonymous reads)
+
+        Args:
+            server: Server object (from _create_servers) with TLS pre-configured.
+
+        Returns:
+            Connection: Bound connection (service account or anonymous).
+        """
+        # Determine auto_bind mode based on TLS configuration
+        # CRITICAL: Must use AUTO_BIND_TLS_BEFORE_BIND for STARTTLS to encrypt passwords
+        auto_bind_mode: Literal["DEFAULT", "NONE", "NO_TLS", "TLS_BEFORE_BIND", "TLS_AFTER_BIND"]
+        if self.config.tls_mode == "starttls":
+            auto_bind_mode = AUTO_BIND_TLS_BEFORE_BIND
+        else:
+            # LDAPS: TLS already active via use_ssl=True on Server, bind normally
+            # Plaintext (none): No TLS, bind normally
+            auto_bind_mode = AUTO_BIND_NO_TLS
+
+        if self.config.bind_dn and self.config.bind_password:
+            # Service account bind using ldap3's auto_bind feature.
+            #
+            # Socket Cleanup Note (ldap3 library behavior):
+            #   ldap3's auto_bind has inconsistent socket cleanup on failure:
+            #   - LDAPS mode: _cleanup_socket() called on TLS wrap failure (base.py:292)
+            #   - STARTTLS mode: NO cleanup if wrap_socket raises in _start_tls (tls.py:287-291)
+            #   - bind() failure: NO cleanup, exception propagates up
+            #   - start_tls() returns False: unbind() IS called (connection.py:424)
+            #
+            #   If the constructor raises (during _do_auto_bind), the socket may leak until
+            #   Python's GC collects the Connection object. This is acceptable because:
+            #   1. GC will eventually close the socket (Connection has no __del__, but socket does)
+            #   2. This only affects service account bind during TLS/bind failures (rare)
+            #   3. Phoenix has timeouts (10s connect, 30s operations) preventing hangs
+            #   4. Rate limiting prevents attackers from rapidly triggering many leaks
+            #
+            #   The anonymous bind path below has explicit cleanup because we control the
+            #   sequencing. For service account binds, we rely on ldap3's auto_bind which
+            #   handles the common success case correctly.
+            #
+            #   See: https://github.com/cannatag/ldap3 for upstream library
+            return Connection(
+                server,
+                user=self.config.bind_dn,
+                password=self.config.bind_password,
+                auto_bind=auto_bind_mode,
+                raise_exceptions=True,
+                receive_timeout=30,  # Timeout for LDAP operations (bind, search)
+                # SECURITY: Disable referral following to prevent credential leakage.
+                # ldap3 defaults to following referrals to ANY server and sending credentials.
+                # An attacker-controlled referral could steal service account credentials.
+                # Phoenix already has multi-server failover, so referrals are unnecessary.
+                auto_referrals=False,
+            )
+
+        # Anonymous bind case - must manually sequence open/start_tls before bind
+        #
+        # AUTO_BIND_DEFAULT defers bind() until the context manager is entered.
+        # This is NOT the same as AUTO_BIND_NONE (which skips bind entirely).
+        #
+        # Why not AUTO_BIND_TLS_BEFORE_BIND?
+        #   That performs open→start_tls→bind atomically in the constructor.
+        #   For anonymous binds (no user/password), we need manual sequencing
+        #   to ensure start_tls() completes before bind(). The sequence is:
+        #
+        #   1. Connection() - creates connection object (no network I/O)
+        #   2. open() - establishes TCP connection
+        #   3. start_tls() - upgrades to TLS (for STARTTLS mode)
+        #   4. return conn - caller uses `with conn:` which triggers bind()
+        #
+        #   This ensures TLS is active before any bind credentials are sent.
+        conn = Connection(
+            server,
+            auto_bind=AUTO_BIND_DEFAULT,
+            raise_exceptions=True,
+            receive_timeout=30,
+            # SECURITY: Disable referral following (see service account connection above)
+            auto_referrals=False,
+        )
+        try:
+            conn.open()
+            # Upgrade to TLS for STARTTLS mode before any bind operations
+            if self.config.tls_mode == "starttls":
+                conn.start_tls()
+            return conn
+        except Exception:
+            # CRITICAL: Unbind on any exception to prevent socket leak
+            # Threat: open() or start_tls() may open a socket but raise before bind.
+            # Without cleanup, repeated TLS handshake failures would leak file descriptors
+            # and eventually exhaust the process (DoS). unbind() safely closes socket
+            # even if connection was never bound.
+            conn.unbind()  # type: ignore[no-untyped-call]
+            raise
+
+    async def authenticate(self, username: str, password: str) -> LDAPUserInfo | None:
+        """Authenticate user against LDAP and return user info.
+
+        This method performs the following steps:
+        1. Connect to LDAP server (with failover if multiple servers configured)
+        2. Bind with service account (if configured) or directly with user credentials
+        3. Search for user by username
+        4. Authenticate user (bind with user's credentials)
+        5. Retrieve user attributes (email, display name)
+        6. Query user's group memberships
+        7. Map groups to Phoenix role
+
+        Performance & Security - Thread Pool Isolation:
+            All LDAP operations (connection, TLS handshake, bind, search) are executed
+            in a thread pool to prevent blocking the FastAPI event loop.
+
+            Why this matters (DoS prevention):
+            - ldap3 library is synchronous-only (blocks calling thread)
+            - Without isolation, each /auth/ldap/login blocks the event loop
+            - Attacker opens slow TLS handshakes → starves all FastAPI workers
+            - Even rate-limited requests would queue indefinitely
+
+            Mitigation: anyio.to_thread.run_sync() runs LDAP ops in background threads,
+            keeping the main event loop responsive for other requests.
+
+        Timeout Architecture (Defense-in-Depth):
+            Multiple timeout layers ensure no single failure can hang the system:
+
+            ┌─────────────────────────────────────────────────────────────┐
+            │ HTTP Request: 60s (anyio.fail_after)                        │
+            │   Returns 500 to client if exceeded; thread continues       │
+            │  ┌─────────────────────────────────────────────────────────┐│
+            │  │ Thread Pool Task (no direct timeout)                    ││
+            │  │   Runs until LDAP operation completes or socket times out│
+            │  │  ┌─────────────────────────────────────────────────────┐││
+            │  │  │ LDAP Operation: 30s (receive_timeout)               │││
+            │  │  │   Bind, search, and other LDAP protocol operations  │││
+            │  │  │  ┌─────────────────────────────────────────────────┐│││
+            │  │  │  │ TCP Connect: 10s (connect_timeout)              ││││
+            │  │  │  │   Initial socket connection to LDAP server      ││││
+            │  │  │  └─────────────────────────────────────────────────┘│││
+            │  │  └─────────────────────────────────────────────────────┘││
+            │  └─────────────────────────────────────────────────────────┘│
+            └─────────────────────────────────────────────────────────────┘
+
+            Rationale for each layer:
+            - TCP Connect (10s): Network unreachable or firewall should fail fast
+            - LDAP Operation (30s): Bind/search should complete quickly; slow response
+              indicates server overload. This is the actual timeout that stops the thread.
+            - HTTP Request (60s): Prevents client from hanging indefinitely. Note that
+              Python threads running native C code cannot be cancelled, so this only
+              returns an error to the client—the thread continues until socket timeout.
+
+            Multi-Server Failover & Load Distribution:
+            When multiple LDAP servers are configured, they are shuffled randomly on each
+            authentication attempt. This provides load distribution across replicas and
+            prevents a slow primary from always causing delays. Failover to the next
+            server occurs on LDAPException (connection failure, timeout, etc.).
+
+            Each server attempt can take up to 30s (receive_timeout) if the server
+            accepts TCP but doesn't respond to LDAP ops.
+
+            With N unresponsive servers: N × 30s total time before all servers exhausted.
+            - 1 server: 30s max (well within 60s HTTP timeout)
+            - 2 servers: 60s max (equals HTTP timeout—may return before 2nd completes)
+            - 3+ servers: exceeds 60s (HTTP timeout fires, not all servers tried)
+
+            This is an intentional trade-off: the 60s HTTP timeout prioritizes client
+            experience over exhaustively trying all servers. In practice, if multiple
+            servers are all unresponsive, the infrastructure has larger problems. The
+            60s limit also aligns with common load balancer timeouts (nginx, AWS ALB).
+
+        Security:
+            - Empty username/password rejected (prevents anonymous bind bypass)
+            - LDAP injection prevention via RFC 4515 escaping (blocks filter manipulation)
+            - Exception sanitization (no internal server details leaked to attackers)
+            - Thread pool isolation prevents event loop DoS (slow LDAP can't block other requests)
+            - Timeouts prevent resource exhaustion (hanging threads would accumulate)
+            - Socket cleanup prevents file descriptor leaks (failed binds close connections)
+            - Timing attack mitigation via dummy bind (prevents username enumeration)
+
+        Args:
+            username: LDAP username (e.g., "jdoe" for Active Directory sAMAccountName)
+            password: User's password
+
+        Returns:
+            LDAPUserInfo object or None if authentication fails (including timeout)
+        """
+        # Run synchronous ldap3 operations in thread pool to avoid blocking event loop.
+        #
+        # Concurrency limiting: _get_ldap_limiter() caps concurrent LDAP operations to
+        # prevent thread pool exhaustion during traffic spikes. Requests exceeding the
+        # limit will wait (not fail) until a slot is available.
+        #
+        # Timeout handling: fail_after() prevents HTTP request hang but cannot stop the
+        # thread itself (threads running native code cannot be cancelled). The real
+        # timeout is receive_timeout=30 on Connection objects, which terminates blocking
+        # socket operations inside the thread. We catch TimeoutError to return a clean
+        # authentication failure rather than propagating a 500 error.
+        try:
+            with anyio.fail_after(60):
+                return await anyio.to_thread.run_sync(
+                    self._authenticate,
+                    username,
+                    password,
+                    limiter=_get_ldap_limiter(),
+                )
+        except TimeoutError:
+            # LDAP operation exceeded 60s timeout. This typically means:
+            # 1. LDAP server is overloaded or unresponsive
+            # 2. Network issues causing slow responses
+            # 3. Very slow TLS handshake (e.g., OCSP/CRL checks)
+            #
+            # The background thread continues running until socket timeout (30s),
+            # but we return immediately to the client. Log as error for monitoring.
+            logger.error(
+                "LDAP authentication timed out after 60 seconds. "
+                "Check LDAP server health and network connectivity."
+            )
+            return None
+
+    def _authenticate(self, username: str, password: str) -> LDAPUserInfo | None:
+        """Synchronous LDAP authentication (called from thread pool via authenticate())."""
+        # SECURITY: Reject empty credentials to prevent anonymous bind bypass
+        # Threat: LDAP RFC 4513 §5.1.2 defines Simple Authentication with empty password
+        # as "unauthenticated". Many LDAP servers grant anonymous read access for empty
+        # password (bind succeeds with DN but no actual authentication). An attacker could
+        # send empty password to bypass authentication if we don't explicitly check.
+        if not username or not username.strip():
+            logger.warning("LDAP authentication rejected: empty username")
+            return None
+        if not password:
+            logger.warning("LDAP authentication rejected: empty password")
+            return None
+
+        # SECURITY: Reject oversized credentials to prevent DoS
+        # Threat: Attacker sends megabyte-sized username/password to waste memory,
+        # CPU (escaping, filter building), and LDAP server resources.
+        if len(username) > self._MAX_USERNAME_LENGTH:
+            logger.warning("LDAP authentication rejected: username too long")
+            return None
+        if len(password) > self._MAX_PASSWORD_LENGTH:
+            logger.warning("LDAP authentication rejected: password too long")
+            return None
+
+        # SECURITY: Prevent LDAP filter injection (RFC 4515)
+        # Attack: username="*" or "admin*" or "admin)(uid=*" could bypass authentication
+        # or enumerate users. escape_filter_chars() escapes special LDAP filter characters:
+        # * → \2a, ( → \28, ) → \29, \ → \5c, NUL → \00
+        escaped_username = escape_filter_chars(username)
+
+        # Shuffle servers for load distribution across replicas.
+        # Since LDAP servers are assumed to be replicas with identical data,
+        # randomizing the order prevents the first server from receiving all
+        # initial requests and provides more even load distribution.
+        servers = random.sample(self.servers, len(self.servers))
+        for server in servers:
+            try:
+                # Step 1: Create connection with service account (or anonymous)
+                with self._establish_connection(server) as conn:
+                    # Step 2 & 3: Search for user
+                    user_entry = self._search_user(conn, escaped_username)
+                    if not user_entry:
+                        # TIMING ATTACK MITIGATION: Perform dummy bind to prevent username
+                        # enumeration
+                        #
+                        # Without this, an attacker could distinguish "user not found" from
+                        # "wrong password" by measuring response times:
+                        #   - User not found: Fast response (only search performed)
+                        #   - Wrong password: Slow response (search + bind attempt)
+                        #
+                        # By always performing a bind operation (even with dummy credentials
+                        # when user doesn't exist), both code paths take similar time,
+                        # preventing attackers from enumerating valid usernames.
+                        #
+                        # The dummy DN is intentionally invalid and will always fail bind,
+                        # but the network round-trip and TLS operations equalize timing.
+                        self._dummy_bind_for_timing(server, password)
+                        logger.info("User not found in LDAP directory")
+
+                        # DESIGN DECISION: Return immediately instead of trying other servers
+                        #
+                        # Why not failover to other servers when user is not found?
+                        #
+                        # 1. SEMANTIC CORRECTNESS (primary reason):
+                        #    In a properly configured LDAP environment, "user not found" is a
+                        #    definitive answer. Failover servers are replicas of the same directory
+                        #    and should have identical user sets. If user doesn't exist on server A,
+                        #    they won't exist on server B either. Multi-server failover is designed
+                        #    for server unavailability (LDAPException → continue), not for data
+                        #    inconsistency between replicas.
+                        #
+                        # 2. EDGE CASES (replica lag, AD GC/DC differences):
+                        #    Temporary inconsistencies can occur during replication, but these are
+                        #    rare and transient. Designing around them would add complexity for
+                        #    little practical benefit, and could mask underlying infrastructure
+                        #    issues that should be addressed at the LDAP layer.
+                        return None
+
+                    user_dn = user_entry.entry_dn
+
+                    # Step 4: Authenticate user by binding with their credentials
+                    # We use a separate connection to verify the password to avoid
+                    # dropping the main connection which might be needed for group search.
+                    if not self._verify_user_password(server, user_dn, password):
+                        logger.info("LDAP password verification failed")
+                        return None
+
+                    # Step 5: Extract user attributes
+                    # Email handling depends on whether attr_email is configured:
+                    # - If configured: read from LDAP, fail if missing
+                    # - If empty: email will be None, marker generated later
+                    email: str | None = None
+                    if self.config.attr_email:
+                        email = _get_attribute(user_entry, self.config.attr_email)
+                        if not email:
+                            # Fail loudly: admin configured an attribute that doesn't exist
+                            logger.error(
+                                f"LDAP user missing required email attribute "
+                                f"({self.config.attr_email}). Either populate this attribute "
+                                f"or set PHOENIX_LDAP_ATTR_EMAIL=null"
+                            )
+                            return None
+                    # else: email stays None, will be handled by get_or_create_ldap_user
+
+                    display_name = (
+                        _get_attribute(user_entry, self.config.attr_display_name)
+                        if self.config.attr_display_name
+                        else None
+                    )
+
+                    # Extract unique_id if configured (objectGUID, entryUUID, etc.)
+                    unique_id: str | None = None
+                    if self.config.attr_unique_id:
+                        unique_id = _get_unique_id(user_entry, self.config.attr_unique_id)
+                        if not unique_id:
+                            # Fail loudly: user explicitly configured unique_id, so missing
+                            # attribute indicates misconfiguration (likely typo). Don't silently
+                            # fall back to email - that would mask the error.
+                            logger.error(
+                                f"LDAP user missing configured unique_id attribute "
+                                f"({self.config.attr_unique_id}). "
+                                f"Check PHOENIX_LDAP_ATTR_UNIQUE_ID "
+                                f"spelling. Common values: objectGUID (AD), entryUUID (OpenLDAP)."
+                            )
+                            return None
+
+                    # Step 6: Get user's group memberships
+                    # Reuses the existing service/anonymous connection
+                    groups = self._get_user_groups(conn, user_entry, username)
+
+                    # Step 7: Map groups to Phoenix role
+                    role = self.map_groups_to_role(groups)
+                    if not role:
+                        logger.info(
+                            "LDAP authentication denied: user not member of any configured group. "
+                            "Configure PHOENIX_LDAP_GROUP_ROLE_MAPPINGS to include user's groups."
+                        )
+                        return None
+
+                    return LDAPUserInfo(
+                        email=email,
+                        display_name=display_name or username,
+                        groups=tuple(groups),
+                        user_dn=user_dn,
+                        ldap_username=username,
+                        role=role,
+                        unique_id=unique_id,
+                    )
+
+            except LDAPException as e:
+                # SECURITY: Don't leak internal LDAP server error details
+                # Threat: Exception messages may contain sensitive info (server IPs, DNs,
+                # configuration details, internal paths). Only log error type (e.g.,
+                # "LDAPSocketOpenError") to avoid information disclosure to attackers
+                # monitoring logs or error responses.
+                logger.warning(
+                    f"LDAP server {server.host} failed during authentication. "
+                    f"Error type: {type(e).__name__}"
+                )
+                continue  # Try next server
+
+        # All servers failed
+        logger.error("All LDAP servers failed")
+        return None
+
+    def _search_user(self, conn: Connection, escaped_username: str) -> Entry | None:
+        """Search for user in LDAP directory across all configured search bases.
+
+        Searches each base DN in order until a user is found. This allows organizations
+        with users in multiple OUs (e.g., employees and contractors) to authenticate
+        against a single LDAP configuration.
+
+        Args:
+            conn: Active LDAP connection
+            escaped_username: Escaped username for filter
+
+        Returns:
+            User entry or None if not found or ambiguous
+        """
+        user_filter = self.config.user_search_filter.replace("%s", escaped_username)
+
+        # Build attribute list - filter out None values (e.g., attr_email in no-email mode)
+        attributes = [
+            attr
+            for attr in [
+                self.config.attr_email,
+                self.config.attr_display_name,
+                self.config.attr_member_of,
+                self.config.attr_unique_id,
+                self.config.group_search_filter_user_attr,
+            ]
+            if attr  # Filter out None and empty strings
+        ]
+
+        # Search each base DN in order
+        for search_base in self.config.user_search_base_dns:
+            conn.search(
+                search_base=search_base,
+                search_filter=user_filter,
+                search_scope=SUBTREE,
+                attributes=attributes,
+            )
+
+            if len(conn.entries) == 0:
+                # Not found in this base, try next
+                continue
+            elif len(conn.entries) > 1:
+                # SECURITY: Reject ambiguous results to prevent non-deterministic authentication
+                # Attack scenario: Username "jsmith" exists in both ou=contractors,dc=corp and
+                # ou=employees,dc=corp. Blindly taking first result means authentication outcome
+                # depends on LDAP server's arbitrary ordering (could change between queries).
+                # This allows an attacker to exploit timing or replica inconsistencies.
+                logger.error(
+                    f"Ambiguous LDAP search: found {len(conn.entries)} matching entries "
+                    f"in search base '{search_base}'. Rejecting authentication for safety. "
+                    f"Fix: Use more specific user_search_filter to ensure unique results."
+                )
+                return None
+            else:
+                # Exactly one match - success
+                return cast(Entry, conn.entries[0])
+
+        # Not found in any search base
+        logger.info("LDAP user search returned no results in any configured search base")
+        return None
+
+    def _dummy_bind_for_timing(self, server: Server, password: str) -> None:
+        """Perform a dummy bind to equalize response timing when user is not found.
+
+        Timing Attack Prevention:
+            This method exists solely to prevent username enumeration via timing attacks.
+
+            Attack scenario without mitigation:
+                1. Attacker sends login request with "admin" / "wrongpass"
+                2. If "admin" exists: search succeeds → bind attempted → ~150ms response
+                3. If "admin" doesn't exist: search fails → immediate return → ~50ms response
+                4. Attacker measures response times to enumerate valid usernames
+
+            Mitigation:
+                When a user is not found, we still perform a bind operation against
+                a known-invalid DN. This ensures both "user not found" and "wrong password"
+                code paths perform similar network operations (TLS handshake, bind attempt),
+                making response times indistinguishable.
+
+            Why this works:
+                The timing-sensitive operations are network I/O (TLS, LDAP protocol).
+                By performing the same I/O operations regardless of whether the user exists,
+                we eliminate the timing side-channel. The dummy bind will always fail
+                (invalid DN), but the network round-trip equalizes timing.
+
+        Args:
+            server: LDAP server to connect to (same as real bind).
+            password: User-provided password (used for realistic timing).
+        """
+        # Use a randomized invalid DN to prevent caching/optimization by LDAP server
+        # The actual credentials don't matter - we just need the network round-trip
+        dummy_dn = f"cn=dummy-{token_hex(8)},dc=invalid,dc=local"
+        try:
+            self._verify_user_password(server, dummy_dn, password)
+        except Exception:
+            # Expected to fail - we only care about the timing, not the result
+            pass
+
+    def _verify_user_password(self, server: Server, user_dn: str, password: str) -> bool:
+        """Verify user's password by attempting to bind as that user.
+
+        TLS Sequencing for STARTTLS:
+            Unlike _establish_connection (which uses AUTO_BIND_TLS_BEFORE_BIND),
+            this method uses manual sequencing:
+
+            1. Create connection with auto_bind=False
+            2. Open connection (plaintext for STARTTLS)
+            3. Call start_tls() explicitly (upgrade to TLS)
+            4. Call bind() with user credentials (now encrypted)
+
+        Why Manual Sequencing?
+            We need explicit error handling between open() and bind() to ensure
+            socket cleanup in the finally block. AUTO_BIND_TLS_BEFORE_BIND would
+            combine steps 2-4 into a single auto_bind call, hiding exceptions and
+            making it harder to guarantee socket cleanup on partial failures.
+            Manual sequencing gives us fine-grained control over error paths.
+
+        TLS Modes:
+            STARTTLS: start_tls() called before bind() to encrypt credentials
+            LDAPS: TLS already active from Server (use_ssl=True), bind directly
+            Plaintext: No TLS, bind directly (testing only)
+
+        Security Note:
+            Skipping start_tls() for STARTTLS mode would transmit the password
+            in plaintext despite TLS being "enabled" in configuration.
+
+        Exception Handling:
+            LDAPInvalidCredentialsResult is caught and returns False (wrong password).
+            Other LDAPExceptions (server errors, timeouts) are re-raised to trigger
+            failover to the next server in _authenticate().
+
+        Args:
+            server: Server object with TLS pre-configured.
+            user_dn: User's Distinguished Name (e.g., "uid=alice,ou=users,dc=example,dc=com").
+            password: User's password to verify.
+
+        Returns:
+            bool: True if bind succeeds (password valid), False otherwise.
+
+        Raises:
+            LDAPException: For connection/server errors (NOT invalid credentials).
+        """
+        user_conn = Connection(
+            server,
+            user=user_dn,
+            password=password,
+            auto_bind=AUTO_BIND_NONE,  # No auto-bind; we call open/start_tls/bind manually
+            raise_exceptions=True,
+            receive_timeout=30,  # Timeout for bind operation
+            # SECURITY: Disable referral following to prevent credential leakage
+            auto_referrals=False,
+        )
+        try:
+            user_conn.open()
+            # CRITICAL: Upgrade to TLS BEFORE sending password for STARTTLS mode
+            if self.config.tls_mode == "starttls":
+                user_conn.start_tls()
+            user_conn.bind()
+            return user_conn.bound
+        except LDAPInvalidCredentialsResult:
+            # Wrong password - return False instead of raising.
+            # This prevents invalid credentials from triggering server failover
+            # in _authenticate() (failover is for server errors, not auth failures).
+            return False
+        finally:
+            # CRITICAL: Always unbind to prevent socket leak
+            # Threat: If open() or start_tls() or bind() raises, connection has an open
+            # socket but bound=False. Conditional cleanup (if user_conn.bound: unbind())
+            # would skip cleanup, leaking the file descriptor. Repeated failed logins
+            # would exhaust process FD limit (typically 1024) causing service crash.
+            # unbind() safely closes socket regardless of bind state.
+            user_conn.unbind()  # type: ignore[no-untyped-call]
+
+    def _get_user_groups(self, conn: Connection, user_entry: Entry, username: str) -> list[str]:
+        """Get user's group memberships.
+
+        Two modes are supported, determined by group_search_filter presence:
+
+        AD Mode (group_search_filter NOT set):
+            Reads the memberOf attribute directly from the user entry.
+            This is the recommended approach for Active Directory, which
+            automatically populates memberOf with the user's group DNs.
+
+        Search Mode (group_search_filter IS set):
+            Searches for groups that contain the user. Used for POSIX groups
+            (posixGroup) or when memberOf is not available.
+
+            The %s placeholder in the filter is replaced with:
+            - If group_search_filter_user_attr is set: That attribute's value
+              from the user entry (e.g., uid="jdoe" or distinguishedName="...")
+            - If not set: The login username directly
+
+            Common patterns:
+            - POSIX (memberUid=%s): memberUid contains usernames like "jdoe"
+              → Use username directly (default) or group_search_filter_user_attr=uid
+            - groupOfNames (member=%s): member contains full DNs
+              → Requires group_search_filter_user_attr=distinguishedName (AD only)
+
+        Size Limit Warning:
+            If the LDAP server's size limit is exceeded (commonly 1000 entries),
+            a warning is logged and partial results are returned. This can cause
+            users to receive incorrect role mappings if their groups are not in
+            the returned subset. Configure more specific group_search_base_dns
+            or increase the server's sizelimit if this occurs.
+
+        Args:
+            conn: Active LDAP connection (with service account if configured)
+            user_entry: User entry from search
+            username: User's login username (used as default filter value)
+
+        Returns:
+            List of group DNs (Distinguished Names)
+        """
+        # Mode determined by group_search_filter presence
+        if not self.config.group_search_filter:
+            if not self.config.attr_member_of:
+                return []
+            # AD mode: Read memberOf attribute from user entry
+            member_of = _get_attribute(user_entry, self.config.attr_member_of, multiple=True)
+            return member_of if member_of else []
+
+        # POSIX mode: Search for groups containing this user
+        groups: list[str] = []
+        group_search_filter = self.config.group_search_filter
+        if self.config.group_search_base_dns:
+            # Determine what value to substitute for %s in the filter
+            # - If group_search_filter_user_attr is set: Use that attribute's value
+            #   (e.g., "uid" -> "admin")
+            # - If not set: Use the username
+            #
+            # POSIX memberUid contains usernames ("admin"), not full DNs.
+            if self.config.group_search_filter_user_attr:
+                # Get the specified attribute value from the user entry
+                filter_value = _get_attribute(user_entry, self.config.group_search_filter_user_attr)
+                if not filter_value:
+                    # Attribute not found on user - can't search for groups
+                    attr = self.config.group_search_filter_user_attr
+                    logger.warning(
+                        f"User entry missing attribute '{attr}' required for group search filter"
+                    )
+                    return []
+            else:
+                # use the username
+                filter_value = username
+
+            # SECURITY: Escape value for LDAP filter (RFC 4515)
+            # Threat: Values can contain special chars like parentheses, asterisks, backslashes
+            # (e.g., "user(contractor)*"). If inserted into filter unescaped,
+            # these could break filter syntax or allow injection. Always escape before
+            # string substitution, even though value comes from trusted LDAP server.
+            escaped_value = escape_filter_chars(filter_value)
+            group_filter = group_search_filter.replace("%s", escaped_value)
+
+            # Search each group base DN and collect groups from all
+            for group_search_base in self.config.group_search_base_dns:
+                try:
+                    conn.search(
+                        search_base=group_search_base,
+                        search_filter=group_filter,
+                        search_scope=SUBTREE,
+                        attributes=["cn"],
+                    )
+
+                    # Check if results were truncated by server's size limit
+                    # ldap3 doesn't raise for sizeLimitExceeded, it returns partial results
+                    if conn.result and conn.result.get("result") == RESULT_SIZE_LIMIT_EXCEEDED:
+                        logger.warning(
+                            f"LDAP group search hit server size limit for base "
+                            f"'{group_search_base}'. Results may be incomplete. "
+                            f"Consider using more specific group_search_base_dns or "
+                            f"increasing the server's sizelimit."
+                        )
+
+                    for group_entry in conn.entries:
+                        groups.append(group_entry.entry_dn)
+                except LDAPException as e:
+                    # SECURITY: Don't leak internal LDAP server error details
+                    logger.warning(
+                        f"LDAP group search failed for base '{group_search_base}'. "
+                        f"Error type: {type(e).__name__}"
+                    )
+
+        return groups
+
+    def map_groups_to_role(self, group_dns: list[str]) -> AssignableUserRoleName | None:
+        """Map LDAP group DNs to Phoenix role.
+
+        Mapping Behavior:
+            - Iterates through mappings in configuration order (first match wins)
+            - Supports wildcard "*" to match all users
+            - Case-insensitive DN matching per RFC 4514
+            - DN normalization via canonicalize_dn to handle spacing/order/escape differences
+
+        Design Decision - First Match Wins vs. Highest Role Wins:
+            This implementation uses "first match wins" (configuration order determines
+            priority) rather than "highest role wins" (role hierarchy determines priority).
+            This matches Grafana's LDAP behavior and is the common pattern in authorization
+            systems (firewall rules, nginx routing, ACLs).
+
+            Rationale:
+            1. Explicit administrator control: Config order gives admins full control over
+               precedence. Role-level priority locks you into a fixed hierarchy (ADMIN >
+               MEMBER > VIEWER), but organizations may have complex access rules that don't
+               map cleanly to role hierarchy.
+
+            2. Simplicity and predictability: Easy to reason about ("whatever comes first
+               in config wins") and easy to debug (just look at config order). No hidden
+               logic comparing role levels.
+
+            3. Industry convention: Matches behavior in firewalls (iptables), web servers
+               (nginx location blocks), and access control lists. Administrators familiar
+               with these systems expect "first match wins."
+
+            4. No role hierarchy maintenance: Role-level priority requires defining and
+               maintaining a hierarchy. What if custom roles are added later? First-match
+               avoids this complexity entirely.
+
+            Trade-off:
+                Misconfigured ordering can accidentally give users lower access than
+                intended. This is considered acceptable because it's explicit and
+                auditable in the configuration.
+
+            Configuration Best Practice:
+                Order mappings from highest privilege to lowest:
+                    [
+                        {"group_dn": "cn=admins,ou=groups,dc=example,dc=com", "role": "ADMIN"},
+                        {"group_dn": "cn=developers,ou=groups,dc=example,dc=com", "role": "MEMBER"},
+                        {"group_dn": "*", "role": "VIEWER"}  # Catch-all fallback
+                    ]
+
+        Args:
+            group_dns: List of LDAP group DNs the user is a member of
+
+        Returns:
+            Phoenix role name (ADMIN, MEMBER, VIEWER) or None if no match
+
+        See Also:
+            Grafana's equivalent implementation:
+            https://github.com/grafana/grafana/blob/main/pkg/services/ldap/ldap.go
+            (buildGrafanaUser function, "only use the first match for each org" comment)
+        """
+        # Normalize user group DNs once to avoid repeated canonicalization
+        # Filter out None values (DNs that failed to parse) with warning
+        canonical_user_groups: set[str] = set()
+        for dn in group_dns:
+            canonical = canonicalize_dn(dn)
+            if canonical is not None:
+                canonical_user_groups.add(canonical)
+            else:
+                # Log warning but don't include the DN itself (may contain sensitive info)
+                logger.warning(
+                    "Failed to canonicalize group DN from LDAP server. "
+                    "This group will be ignored for role mapping. "
+                    "This may indicate malformed data in the LDAP directory."
+                )
+
+        # Iterate through mappings in priority order (first match wins)
+        for mapping in self.config.group_role_mappings:
+            group_dn = mapping["group_dn"]
+            role = mapping["role"]
+
+            # Check if user matches this mapping
+            if _is_member_of(canonical_user_groups, group_dn):
+                return role  # Already validated and normalized to uppercase at config load
+
+        # No matching groups - deny access
+        return None
+
+
+@overload
+def _get_attribute(
+    entry: Entry, attr_name: str, multiple: Literal[False] = False
+) -> str | None: ...
+
+
+@overload
+def _get_attribute(entry: Entry, attr_name: str, multiple: Literal[True]) -> list[str] | None: ...
+
+
+def _get_attribute(entry: Entry, attr_name: str, multiple: bool = False) -> str | list[str] | None:
+    """Safely extract attribute value from LDAP entry.
+
+    Args:
+        entry: LDAP entry object
+        attr_name: Attribute name to extract
+        multiple: If True, return list of values; otherwise return first value
+
+    Returns:
+        Attribute value(s) or None if not present
+    """
+    if not attr_name:
+        return None
+
+    attr = getattr(entry, attr_name, None)
+    if attr is None:
+        return None
+
+    values = attr.values if hasattr(attr, "values") else []
+    if not values:
+        return None
+
+    if multiple:
+        return list(values)
+    return str(values[0])
+
+
+def _get_unique_id(entry: Entry, attr_name: str) -> str | None:
+    """Extract unique identifier attribute, handling binary values.
+
+    Different LDAP servers store unique identifiers in different formats:
+
+    - Active Directory objectGUID: Binary (16 bytes, mixed-endian)
+    - OpenLDAP entryUUID: String (RFC 4530)
+    - 389 DS nsUniqueId: String
+
+    This method handles both binary and string formats, returning a
+    standard UUID string representation for consistency.
+
+    IMPORTANT - Database Compatibility:
+        The returned string is used as a database key for user lookup.
+        To ensure consistent matching:
+        - Output is always lowercase (UUIDs are case-insensitive per RFC 4122)
+        - Whitespace is stripped
+        - Empty values return None
+
+        If an existing database entry has different casing (e.g., uppercase
+        from an older version), the user will be found via email fallback
+        and their unique_id will be updated on next login.
+
+    Active Directory objectGUID Binary Format (MS-DTYP §2.3.4):
+        Microsoft's GUID structure uses mixed-endian byte ordering:
+
+        | Field | Size    | Endianness    | Wire bytes for "2212e4c7-..." |
+        |-------|---------|---------------|-------------------------------|
+        | Data1 | 4 bytes | Little-endian | c7 e4 12 22                   |
+        | Data2 | 2 bytes | Little-endian | 1e 05                         |
+        | Data3 | 2 bytes | Little-endian | 0c 4d                         |
+        | Data4 | 8 bytes | Big-endian    | 9a 5b 12 77 0a 9b b7 ab       |
+
+        Python's uuid.UUID(bytes_le=...) expects exactly this format.
+
+    References:
+        - MS-DTYP §2.3.4: https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-dtyp/001eec5a-7f8b-4293-9e21-ca349392db40
+        - MS-ADA3 objectGUID: https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-ada3/937eb5c6-f6b3-4652-a276-5d6bb8979658
+        - RFC 4530 entryUUID: https://www.rfc-editor.org/rfc/rfc4530.html
+
+    Args:
+        entry: LDAP entry object from ldap3
+        attr_name: Attribute name (e.g., "objectGUID", "entryUUID")
+
+    Returns:
+        String representation of the unique ID (lowercase UUID format),
+        or None if not present or empty
+    """  # noqa: E501
+    if not attr_name:
+        return None
+
+    attr = getattr(entry, attr_name, None)
+    if attr is None:
+        return None
+
+    # Get raw value - could be bytes (objectGUID) or str (entryUUID)
+    # ldap3's decode_raw_vals (search.py:410-411) returns:
+    #   - [bytes(val) for val in vals] if vals has items (always bytes, never str)
+    #   - None if vals is empty/falsy (NOT an empty list)
+    # The `and attr.raw_values` check handles both None and empty list cases.
+    raw_value = attr.raw_values[0] if hasattr(attr, "raw_values") and attr.raw_values else None
+    if raw_value is None:
+        return None
+
+    # Handle binary values (AD objectGUID is 16 bytes)
+    # ldap3 always returns bytes, but we accept bytearray/memoryview for defensive coding
+    if isinstance(raw_value, (bytes, bytearray, memoryview)):
+        raw_bytes = bytes(raw_value)  # Normalize to bytes for uuid.UUID
+
+        # Empty bytes should return None, not empty string
+        if len(raw_bytes) == 0:
+            return None
+
+        if len(raw_bytes) == 16:
+            import uuid
+
+            # ASSUMPTION: 16-byte values are binary UUIDs (e.g., AD objectGUID).
+            # Custom 16-character string IDs are NOT supported - see LDAPConfig docs.
+            #
+            # MS-DTYP §2.3.4: GUID uses mixed-endian format
+            # Data1/Data2/Data3 are little-endian, Data4 is big-endian
+            # Python's bytes_le parameter handles this correctly
+            # Note: uuid.UUID always returns lowercase
+            return str(uuid.UUID(bytes_le=raw_bytes))
+        else:
+            # Non-16-byte value: likely a string UUID (e.g., OpenLDAP entryUUID)
+            # OpenLDAP stores entryUUID as string "550e8400-e29b-41d4-a716-446655440000"
+            # which comes as bytes b"550e8400-..." (36 bytes) - decode as UTF-8
+            try:
+                decoded = raw_bytes.decode("utf-8").strip()
+                # Return None for empty strings after stripping
+                if not decoded:
+                    return None
+                # Normalize to lowercase for consistent DB lookups
+                # (UUIDs are case-insensitive per RFC 4122 §3)
+                return decoded.lower()
+            except UnicodeDecodeError:
+                # Truly binary format we don't recognize - hex encode for safety
+                # Hex is already lowercase
+                return raw_bytes.hex()
+
+    # String value (shouldn't happen with ldap3, but handle for safety)
+    result = str(raw_value).strip()
+    return result.lower() if result else None
+
+
+def _is_member_of(canonical_user_groups: set[str], target_group: str) -> bool:
+    """Check if user is member of LDAP group.
+
+    Matching logic:
+    - Wildcard "*" matches all users (useful for default roles)
+    - Case-insensitive DN comparison per RFC 4514
+    - Canonical DN comparison to account for spacing/order/escape differences
+
+    Args:
+        canonical_user_groups: Set of canonicalized group DNs the user is a member of
+        target_group: Target group DN to check (or "*" for wildcard)
+
+    Returns:
+        True if user is a member of the target group, False otherwise.
+        Returns False if target_group cannot be canonicalized (configuration error).
+    """
+    # Wildcard matches everyone
+    if target_group == "*":
+        return True
+
+    # Canonical comparison handles ordering/spacing/escaping differences
+    target_canonical = canonicalize_dn(target_group)
+    if target_canonical is None:
+        # Configuration error: admin-provided group DN in PHOENIX_LDAP_GROUP_ROLE_MAPPINGS
+        # cannot be parsed. Log error and return False (no match) to fail safely.
+        logger.error(
+            "Failed to canonicalize configured group DN in PHOENIX_LDAP_GROUP_ROLE_MAPPINGS. "
+            "This mapping will never match. Check DN syntax in configuration."
+        )
+        return False
+
+    return target_canonical in canonical_user_groups