the37lab-authlib 0.1.1751371611__py3-none-any.whl → 0.1.1762438606__py3-none-any.whl

the37lab_authlib/auth.py

@@ -1,4 +1,5 @@
 import inspect
+import inspect
 from flask import Blueprint, request, jsonify, current_app, url_for, redirect, g
 import jwt
 from datetime import datetime, timedelta
@@ -10,18 +11,38 @@ import requests
 import bcrypt
 import logging
 import os
+import re
 from functools import wraps
+from isodate import parse_duration
+import threading
+import time
+import msal
+import smtplib
+from email.mime.text import MIMEText
+from email.mime.multipart import MIMEMultipart
 
 logging.basicConfig(level=logging.DEBUG)
 logger = logging.getLogger(__name__)
 
 class AuthManager:
-    def __init__(self, app=None, db_dsn=None, jwt_secret=None, oauth_config=None, id_type='integer', environment_prefix=None, api_tokens=None):
+    def __init__(self, app=None, db_dsn=None, jwt_secret=None, oauth_config=None, id_type='integer', environment_prefix=None, api_tokens=None, cache_ttl=10, allow_oauth_auto_create=None, email_username=None, email_password=None, email_address=None, email_reply_to=None, email_server=None, email_port=None):
         self.user_override = None
-        if environment_prefix:
-            prefix = environment_prefix.upper() + '_'
-            db_dsn = os.getenv(f'{prefix}DATABASE_URL')
-            jwt_secret = os.getenv(f'{prefix}JWT_SECRET')
+        self._user_cache = {}
+        self._cache_ttl = cache_ttl or 10  # 10 seconds
+        self._last_used_updates = {}  # Track pending updates
+        self._update_lock = threading.Lock()
+        self._update_thread = None
+        self._shutdown_event = threading.Event()
+
+        # Determine prefix: empty if environment_prefix is None/empty, otherwise use it with '_' delimiter
+        prefix = (environment_prefix.upper() + '_') if environment_prefix else ''
+        
+        # Arguments have priority over environment variables
+        db_dsn = db_dsn or os.getenv(f'{prefix}DATABASE_URL')
+        jwt_secret = jwt_secret or os.getenv(f'{prefix}JWT_SECRET')
+        
+        # OAuth config: use argument if provided, otherwise build from env vars
+        if oauth_config is None:
             google_client_id = os.getenv(f'{prefix}GOOGLE_CLIENT_ID')
             google_client_secret = os.getenv(f'{prefix}GOOGLE_CLIENT_SECRET')
             oauth_config = {}
@@ -30,6 +51,19 @@ class AuthManager:
                     'client_id': google_client_id,
                     'client_secret': google_client_secret
                 }
+        
+        # OAuth auto-create: use argument if provided, otherwise check env var (defaults to False)
+        if allow_oauth_auto_create is not None:
+            self.allow_oauth_auto_create = allow_oauth_auto_create
+        else:
+            auto_create_env = os.getenv(f'{prefix}OAUTH_ALLOW_AUTO_CREATE')
+            if auto_create_env is not None:
+                self.allow_oauth_auto_create = auto_create_env.lower() in ['1', 'true', 'yes']
+            else:
+                self.allow_oauth_auto_create = False
+        
+        # API tokens: use argument if provided, otherwise parse from env var
+        if api_tokens is None:
             api_tokens_env = os.getenv(f'{prefix}API_TOKENS')
             if api_tokens_env:
                 api_tokens = {}
@@ -37,9 +71,21 @@ class AuthManager:
                     if ':' in entry:
                         key, user = entry.split(':', 1)
                         api_tokens[key.strip()] = user.strip()
-            user_override_env = os.getenv(f'{prefix}USER_OVERRIDE')
-            if user_override_env:
-                self.user_override = user_override_env
+        
+        # User override: use argument if provided, otherwise check env var
+        user_override_env = os.getenv(f'{prefix}USER_OVERRIDE')
+        if user_override_env:
+            self.user_override = user_override_env
+        
+        # Email configuration: arguments have priority
+        email_username = email_username or os.getenv(f'{prefix}EMAIL_USERNAME')
+        email_password = email_password or os.getenv(f'{prefix}EMAIL_PASSWORD')
+        email_address = email_address or os.getenv(f'{prefix}EMAIL_ADDRESS')
+        email_reply_to = email_reply_to or os.getenv(f'{prefix}EMAIL_REPLY_TO')
+        email_server = email_server or os.getenv(f'{prefix}EMAIL_SERVER')
+        email_port = email_port or os.getenv(f'{prefix}EMAIL_PORT')
+            
+        self.expiry_time = parse_duration(os.getenv(f'{prefix}JWT_TOKEN_EXPIRY_TIME', 'PT1H'))
         if self.user_override and (api_tokens or db_dsn):
             raise ValueError('Cannot set user_override together with api_tokens or db_dsn')
         if api_tokens and db_dsn:
@@ -48,18 +94,38 @@ class AuthManager:
         self.db = Database(db_dsn, id_type=id_type) if db_dsn else None
         self.jwt_secret = jwt_secret
         self.oauth_config = oauth_config or {}
+        
+        # Email configuration
+        self.email_username = email_username
+        self.email_password = email_password
+        self.email_address = email_address or email_username
+        if email_reply_to:
+            self.email_reply_to = email_reply_to
+        elif email_username:
+            domain = email_username.split('@')[1] if '@' in email_username else 'localhost'
+            self.email_reply_to = f'noreply@{domain}'
+        else:
+            self.email_reply_to = None
+        self.email_server = email_server
+        self.email_port = int(email_port) if email_port else 587
+        
         self.public_endpoints = {
             'auth.login',
             'auth.oauth_login',
             'auth.oauth_callback',
             'auth.refresh_token',
             'auth.register',
-            'auth.get_roles'
+            'auth.get_roles',
+            'auth.validate_registration',
+            'auth.resend_validation'
         }
         self.bp = None
         
         if app:
             self.init_app(app)
+        
+        # Start the background update thread
+        self._start_update_thread()
 
     def _extract_token_from_header(self):
         auth = request.authorization
@@ -91,17 +157,34 @@ class AuthManager:
             }
         try:
             parsed = ApiToken.parse_token(api_token)
+            
+            # Check cache first
+            cache_key = f"api_token_{parsed['id']}"
+            current_time = datetime.utcnow()
+            
+            if cache_key in self._user_cache:
+                cached_data, cache_time = self._user_cache[cache_key]
+                if (current_time - cache_time).total_seconds() < self._cache_ttl:
+                    logger.debug(f"Returning cached API token data for ID: {parsed['id']}")
+                    return cached_data.copy()  # Return a copy to avoid modifying cache
+            
+            # Cache miss or expired, fetch from database
             with self.db.get_cursor() as cur:
                 # First get the API token record
                 cur.execute("""
-                    SELECT t.*, u.* FROM api_tokens t
+                    SELECT t.*, u.*, r.name as role_name FROM api_tokens t
                     JOIN users u ON t.user_id = u.id
+                    LEFT JOIN user_roles ur ON ur.user_id = u.id
+                    LEFT JOIN roles r ON ur.role_id = r.id
                     WHERE t.id = %s
                 """, (parsed['id'],))
-                result = cur.fetchone()
-                if not result:
+                results = cur.fetchall()
+                if not results:
                     raise AuthError('Invalid API token')
 
+                # Get the first row for token/user data (all rows will have same token/user data)
+                result = results[0]
+                
                 # Verify the nonce
                 if not bcrypt.checkpw(parsed['nonce'].encode('utf-8'), result['token'].encode('utf-8')):
                     raise AuthError('Invalid API token')
@@ -110,29 +193,28 @@ class AuthManager:
                 if result['expires_at'] and result['expires_at'] < datetime.utcnow():
                     raise AuthError('API token has expired')
 
-                # Update last used timestamp
-                cur.execute("""
-                    UPDATE api_tokens 
-                    SET last_used_at = %s
-                    WHERE id = %s
-                """, (datetime.utcnow(), parsed['id']))
+                # Schedule last used timestamp update (asynchronous with 10s delay)
+                self._schedule_last_used_update(parsed['id'])
 
-                # Fetch roles
-                cur.execute("""
-                    SELECT r.name FROM roles r
-                    JOIN user_roles ur ON ur.role_id = r.id
-                    WHERE ur.user_id = %s
-                """, (result['user_id'],))
-                roles = [row['name'] for row in cur.fetchall()]
+                # Extract roles from results
+                roles = [row['role_name'] for row in results if row['role_name'] is not None]
 
                 # Construct user object
-                return {
+                user_data = {
                     'id': result['user_id'],
                     'username': result['username'],
                     'email': result['email'],
                     'real_name': result['real_name'],
                     'roles': roles
                 }
+
+            # Cache the result
+            self._user_cache[cache_key] = (user_data.copy(), current_time)
+            
+            # Clean up expired cache entries
+            self._cleanup_cache()
+            
+            return user_data
         except ValueError:
             raise AuthError('Invalid token format')
 
@@ -238,6 +320,10 @@ class AuthManager:
                 roles = [row['name'] for row in cur.fetchall()]
                 user['roles'] = roles
                 
+                # Check if user is validated
+                if 'validated' not in roles:
+                    raise AuthError('Account not yet validated. Please check your email for the validation link.', 403)
+                
                 token = self._create_token(user)
                 refresh_token = self._create_refresh_token(user)
                 
@@ -251,6 +337,8 @@ class AuthManager:
         def oauth_login():
             provider = request.json.get('provider')
             if provider not in self.oauth_config:
+                logger.error(f"Invalid OAuth provider: {provider}")
+                logger.error(f"These are the known ones: {self.oauth_config.keys()}")
                 raise AuthError('Invalid OAuth provider', 400)
 
             redirect_uri = self.get_redirect_uri()
@@ -265,14 +353,32 @@ class AuthManager:
             
             if not code or not provider:
                 raise AuthError('Invalid OAuth callback', 400)
-
-            user_info = self._get_oauth_user_info(provider, code)
-            token = self._create_token(user_info)
-            refresh_token = self._create_refresh_token(user_info)
+            from urllib.parse import urlencode, urlparse, urlunparse
+            get_redirect_uri = self.get_redirect_uri()
+            parsed_uri = urlparse(get_redirect_uri)
+            frontend_url = os.getenv('FRONTEND_URL', urlunparse((parsed_uri.scheme, parsed_uri.netloc, '', '', '', '')))
             
-            # Redirect to frontend with tokens
-            frontend_url = os.getenv('FRONTEND_URL', 'http://localhost:5173')
-            return redirect(f"{frontend_url}/oauth-callback?token={token}&refresh_token={refresh_token}")
+            #if provider == 'microsoft':
+            #    client = msal.ConfidentialClientApplication(
+            #        self.oauth_config[provider]['client_id'], client_credential=self.oauth_config[provider]['client_secret'], authority=f"https://login.microsoftonline.com/common"
+            #    )
+            #    result = client.acquire_token_by_authorization_code(code, scopes=["email"], redirect_uri=self.get_redirect_uri())
+            #    code = result['access_token']
+            
+            try:
+                user_info = self._get_oauth_user_info(provider, code)
+                token = self._create_token(user_info)
+                refresh_token = self._create_refresh_token(user_info)
+                # Redirect to frontend with tokens
+                return redirect(f"{frontend_url}/oauth-callback?" + urlencode({'token': token, 'refresh_token': refresh_token}))
+            except AuthError as e:
+                # Surface error to frontend for user-friendly messaging
+                params = {
+                    'error': str(e.message) if hasattr(e, 'message') else str(e),
+                    'status': getattr(e, 'status_code', 500),
+                    'provider': provider,
+                }
+                return redirect(f"{frontend_url}/oauth-callback?" + urlencode(params))
 
         @bp.route('/login/profile')
         def profile():
@@ -386,39 +492,501 @@ class AuthManager:
         def register():
             data = request.get_json()
             
-            # Hash the password
             password = data.get('password')
             if not password:
                 raise AuthError('Password is required', 400)
             
+            username = data.get('username')
+            email = data.get('email')
+            
+            if not username:
+                raise AuthError('Username is required', 400)
+            if not email:
+                raise AuthError('Email is required', 400)
+            
+            # Validate password strength
+            self._validate_password_strength(password, username=username, email=email)
+            
+            # Hash the password
             salt = bcrypt.gensalt()
             password_hash = bcrypt.hashpw(password.encode('utf-8'), salt)
             
             user = User(
-                username=data['username'],
-                email=data['email'],
+                username=username,
+                email=email,
                 real_name=data['real_name'],
                 roles=data.get('roles', []),
                 id_generator=self.db.get_id_generator()
             )
 
             with self.db.get_cursor() as cur:
-                if user.id is None:
+                # Check if username or email already exists
+                cur.execute("SELECT id FROM users WHERE username = %s OR email = %s", (username, email))
+                existing_user = cur.fetchone()
+                
+                if existing_user:
+                    user_id = existing_user['id']
+                    
+                    # Check if user is validated
                     cur.execute("""
-                        INSERT INTO users (username, email, real_name, password_hash, created_at, updated_at)
-                        VALUES (%s, %s, %s, %s, %s, %s)
-                        RETURNING id
-                    """, (user.username, user.email, user.real_name, password_hash.decode('utf-8'),
-                          user.created_at, user.updated_at))
-                    user.id = cur.fetchone()['id']
-                else:
+                        SELECT r.name FROM roles r
+                        JOIN user_roles ur ON ur.role_id = r.id
+                        WHERE ur.user_id = %s AND r.name = 'validated'
+                    """, (user_id,))
+                    if cur.fetchone():
+                        # User is validated, reject registration
+                        raise AuthError('Username or email already exists', 400)
+                    
+                    # User exists but not validated - allow re-registration
+                    # This works even if the previous registration hasn't expired yet
+                    # Update existing user with new registration data
+                    cur.execute("""
+                        UPDATE users 
+                        SET username = %s, email = %s, real_name = %s, password_hash = %s, updated_at = %s
+                        WHERE id = %s
+                    """, (username, email, user.real_name, password_hash.decode('utf-8'), datetime.utcnow(), user_id))
+                    
+                    # Remove all existing register-* roles (including non-expired ones)
                     cur.execute("""
-                        INSERT INTO users (id, username, email, real_name, password_hash, created_at, updated_at)
-                        VALUES (%s, %s, %s, %s, %s, %s, %s)
-                    """, (user.id, user.username, user.email, user.real_name, password_hash.decode('utf-8'),
-                          user.created_at, user.updated_at))
+                        DELETE FROM user_roles
+                        WHERE user_id = %s
+                        AND role_id IN (
+                            SELECT id FROM roles WHERE name LIKE 'register-%'
+                        )
+                    """, (user_id,))
+                    
+                    user.id = user_id
+                else:
+                    # New user - create it
+                    if user.id is None:
+                        cur.execute("""
+                            INSERT INTO users (username, email, real_name, password_hash, created_at, updated_at)
+                            VALUES (%s, %s, %s, %s, %s, %s)
+                            RETURNING id
+                        """, (user.username, user.email, user.real_name, password_hash.decode('utf-8'),
+                              user.created_at, user.updated_at))
+                        user.id = cur.fetchone()['id']
+                    else:
+                        cur.execute("""
+                            INSERT INTO users (id, username, email, real_name, password_hash, created_at, updated_at)
+                            VALUES (%s, %s, %s, %s, %s, %s, %s)
+                        """, (user.id, user.username, user.email, user.real_name, password_hash.decode('utf-8'),
+                              user.created_at, user.updated_at))
+                
+                # Generate nonce and timestamp for validation
+                nonce = str(uuid.uuid4())
+                timestamp = int(time.time())
+                role_name = f'register-{nonce}-{timestamp}'
+                
+                # Create temporary validation role
+                cur.execute("SELECT id FROM roles WHERE name = %s", (role_name,))
+                role = cur.fetchone()
+                if not role:
+                    role_obj = Role(role_name, description='Temporary registration validation role', id_generator=self.db.get_id_generator())
+                    if role_obj.id is None:
+                        cur.execute("""
+                            INSERT INTO roles (name, description, created_at)
+                            VALUES (%s, %s, %s)
+                            RETURNING id
+                        """, (role_obj.name, role_obj.description, role_obj.created_at))
+                        role_id = cur.fetchone()['id']
+                    else:
+                        cur.execute("""
+                            INSERT INTO roles (id, name, description, created_at)
+                            VALUES (%s, %s, %s, %s)
+                        """, (role_obj.id, role_obj.name, role_obj.description, role_obj.created_at))
+                        role_id = role_obj.id
+                else:
+                    role_id = role['id']
+                
+                # Associate role with user
+                cur.execute("""
+                    INSERT INTO user_roles (user_id, role_id)
+                    VALUES (%s, %s)
+                    ON CONFLICT (user_id, role_id) DO NOTHING
+                """, (user.id, role_id))
+                
+                # Send validation email
+                frontend_url = self._get_frontend_url()
+                validation_link = f"{frontend_url}/register/{nonce}"
+                email_subject = "Please validate your account"
+                email_body = f"""Hello {user.real_name},
 
-            return jsonify({'id': user.id}), 201
+Thank you for registering. Please click the link below to validate your account:
+
+{validation_link}
+
+This link will expire in 24 hours.
+
+If you did not register for this account, please ignore this email.
+"""
+                self._send_email(user.email, email_subject, email_body)
+
+            return jsonify({'id': user.id, 'message': 'Registration successful. Please check your email for validation link.'}), 201
+
+        @bp.route('/register/<nonce>', methods=['GET'])
+        @bp.public_endpoint
+        def validate_registration(nonce):
+            with self.db.get_cursor() as cur:
+                # Find user with register-{nonce}-{timestamp} role
+                cur.execute("""
+                    SELECT u.id, u.username, u.email, r.name as role_name
+                    FROM users u
+                    JOIN user_roles ur ON ur.user_id = u.id
+                    JOIN roles r ON ur.role_id = r.id
+                    WHERE r.name LIKE %s
+                """, (f'register-{nonce}-%',))
+                results = cur.fetchall()
+                
+                if not results:
+                    raise AuthError('Invalid or expired validation link', 400)
+                
+                # Check if expired (24 hours)
+                current_time = int(time.time())
+                user_id = None
+                expired = True
+                
+                for row in results:
+                    role_name = row['role_name']
+                    if role_name.startswith(f'register-{nonce}-'):
+                        try:
+                            timestamp = int(role_name.split('-')[-1])
+                            if current_time - timestamp < 86400:  # 24 hours
+                                expired = False
+                                user_id = row['id']
+                                break
+                        except (ValueError, IndexError):
+                            continue
+                
+                if expired or not user_id:
+                    raise AuthError('Validation link has expired. Please request a new validation email.', 400)
+                
+                # Remove all register-* roles from user
+                cur.execute("""
+                    DELETE FROM user_roles
+                    WHERE user_id = %s
+                    AND role_id IN (
+                        SELECT id FROM roles WHERE name LIKE 'register-%%'
+                    )
+                """, (user_id,))
+                
+                # Ensure validated role exists
+                cur.execute("SELECT id FROM roles WHERE name = 'validated'")
+                validated_role = cur.fetchone()
+                if not validated_role:
+                    role_obj = Role('validated', description='User has validated their email', id_generator=self.db.get_id_generator())
+                    if role_obj.id is None:
+                        cur.execute("""
+                            INSERT INTO roles (name, description, created_at)
+                            VALUES (%s, %s, %s)
+                            RETURNING id
+                        """, (role_obj.name, role_obj.description, role_obj.created_at))
+                        validated_role_id = cur.fetchone()['id']
+                    else:
+                        cur.execute("""
+                            INSERT INTO roles (id, name, description, created_at)
+                            VALUES (%s, %s, %s, %s)
+                        """, (role_obj.id, role_obj.name, role_obj.description, role_obj.created_at))
+                        validated_role_id = role_obj.id
+                else:
+                    validated_role_id = validated_role['id']
+                
+                # Add validated role to user
+                cur.execute("""
+                    INSERT INTO user_roles (user_id, role_id)
+                    VALUES (%s, %s)
+                    ON CONFLICT (user_id, role_id) DO NOTHING
+                """, (user_id, validated_role_id))
+            
+            return jsonify({'message': 'Account validated successfully. You can now log in.'})
+
+        @bp.route('/resend-validation', methods=['POST'])
+        @bp.public_endpoint
+        def resend_validation():
+            data = request.get_json()
+            email = data.get('email')
+            username = data.get('username')
+            
+            if not email and not username:
+                raise AuthError('Email or username is required', 400)
+            
+            with self.db.get_cursor() as cur:
+                # Find user by email or username
+                if email:
+                    cur.execute("SELECT * FROM users WHERE email = %s", (email,))
+                else:
+                    cur.execute("SELECT * FROM users WHERE username = %s", (username,))
+                user = cur.fetchone()
+                
+                if not user:
+                    # Don't reveal if user exists
+                    return jsonify({'message': 'If an account exists, a validation email has been sent.'})
+                
+                # Check if user is already validated
+                cur.execute("""
+                    SELECT r.name FROM roles r
+                    JOIN user_roles ur ON ur.role_id = r.id
+                    WHERE ur.user_id = %s AND r.name = 'validated'
+                """, (user['id'],))
+                if cur.fetchone():
+                    # User is already validated, don't reveal this
+                    return jsonify({'message': 'If an account exists, a validation email has been sent.'})
+                
+                # Remove existing register-* roles
+                cur.execute("""
+                    DELETE FROM user_roles
+                    WHERE user_id = %s
+                    AND role_id IN (
+                        SELECT id FROM roles WHERE name LIKE 'register-%%'
+                    )
+                """, (user['id'],))
+                
+                # Generate new nonce and timestamp
+                nonce = str(uuid.uuid4())
+                timestamp = int(time.time())
+                role_name = f'register-{nonce}-{timestamp}'
+                
+                # Create new validation role
+                cur.execute("SELECT id FROM roles WHERE name = %s", (role_name,))
+                role = cur.fetchone()
+                if not role:
+                    role_obj = Role(role_name, description='Temporary registration validation role', id_generator=self.db.get_id_generator())
+                    if role_obj.id is None:
+                        cur.execute("""
+                            INSERT INTO roles (name, description, created_at)
+                            VALUES (%s, %s, %s)
+                            RETURNING id
+                        """, (role_obj.name, role_obj.description, role_obj.created_at))
+                        role_id = cur.fetchone()['id']
+                    else:
+                        cur.execute("""
+                            INSERT INTO roles (id, name, description, created_at)
+                            VALUES (%s, %s, %s, %s)
+                        """, (role_obj.id, role_obj.name, role_obj.description, role_obj.created_at))
+                        role_id = role_obj.id
+                else:
+                    role_id = role['id']
+                
+                # Associate role with user
+                cur.execute("""
+                    INSERT INTO user_roles (user_id, role_id)
+                    VALUES (%s, %s)
+                    ON CONFLICT (user_id, role_id) DO NOTHING
+                """, (user['id'], role_id))
+                
+                # Send validation email
+                frontend_url = self._get_frontend_url()
+                validation_link = f"{frontend_url}/register/{nonce}"
+                email_subject = "Please validate your account"
+                email_body = f"""Hello {user['real_name']},
+
+Please click the link below to validate your account:
+
+{validation_link}
+
+This link will expire in 24 hours.
+
+If you did not request this email, please ignore it.
+"""
+                self._send_email(user['email'], email_subject, email_body)
+            
+            return jsonify({'message': 'If an account exists, a validation email has been sent.'})
+
+        @bp.route('/request-password-reset', methods=['POST'])
+        @bp.public_endpoint
+        def request_password_reset():
+            data = request.get_json()
+            username = data.get('username')
+            
+            if not username:
+                raise AuthError('Username is required', 400)
+            
+            with self.db.get_cursor() as cur:
+                # Find user by username
+                cur.execute("SELECT * FROM users WHERE username = %s", (username,))
+                user = cur.fetchone()
+                
+                if not user:
+                    # Don't reveal if user exists
+                    return jsonify({'message': 'If an account exists, a password reset email has been sent.'})
+                
+                # Remove existing password-reset-* roles
+                cur.execute("""
+                    DELETE FROM user_roles
+                    WHERE user_id = %s
+                    AND role_id IN (
+                        SELECT id FROM roles WHERE name LIKE 'password-reset-%%'
+                    )
+                """, (user['id'],))
+                
+                # Generate new nonce and timestamp
+                nonce = str(uuid.uuid4())
+                timestamp = int(time.time())
+                role_name = f'password-reset-{nonce}-{timestamp}'
+                
+                # Create new password reset role
+                cur.execute("SELECT id FROM roles WHERE name = %s", (role_name,))
+                role = cur.fetchone()
+                if not role:
+                    role_obj = Role(role_name, description='Temporary password reset role', id_generator=self.db.get_id_generator())
+                    if role_obj.id is None:
+                        cur.execute("""
+                            INSERT INTO roles (name, description, created_at)
+                            VALUES (%s, %s, %s)
+                            RETURNING id
+                        """, (role_obj.name, role_obj.description, role_obj.created_at))
+                        role_id = cur.fetchone()['id']
+                    else:
+                        cur.execute("""
+                            INSERT INTO roles (id, name, description, created_at)
+                            VALUES (%s, %s, %s, %s)
+                        """, (role_obj.id, role_obj.name, role_obj.description, role_obj.created_at))
+                        role_id = role_obj.id
+                else:
+                    role_id = role['id']
+                
+                # Associate role with user
+                cur.execute("""
+                    INSERT INTO user_roles (user_id, role_id)
+                    VALUES (%s, %s)
+                    ON CONFLICT (user_id, role_id) DO NOTHING
+                """, (user['id'], role_id))
+                
+                # Send password reset email
+                frontend_url = self._get_frontend_url()
+                reset_link = f"{frontend_url}/password-reset/{nonce}"
+                email_subject = "Password Reset Request"
+                email_body = f"""Hello {user['real_name']},
+
+You requested to reset your password. Please click the link below to reset your password:
+
+{reset_link}
+
+This link will expire in 24 hours.
+
+If you did not request a password reset, please ignore this email.
+"""
+                self._send_email(user['email'], email_subject, email_body)
+            
+            return jsonify({'message': 'If an account exists, a password reset email has been sent.'})
+
+        @bp.route('/password-reset/<nonce>', methods=['GET'])
+        @bp.public_endpoint
+        def validate_password_reset(nonce):
+            with self.db.get_cursor() as cur:
+                # Find user with password-reset-{nonce}-{timestamp} role
+                cur.execute("""
+                    SELECT u.id, u.username, u.email, r.name as role_name
+                    FROM users u
+                    JOIN user_roles ur ON ur.user_id = u.id
+                    JOIN roles r ON ur.role_id = r.id
+                    WHERE r.name LIKE %s
+                """, (f'password-reset-{nonce}-%',))
+                results = cur.fetchall()
+                
+                if not results:
+                    raise AuthError('Invalid or expired password reset link', 400)
+                
+                # Check if expired (24 hours)
+                current_time = int(time.time())
+                user_id = None
+                expired = True
+                
+                for row in results:
+                    role_name = row['role_name']
+                    if role_name.startswith(f'password-reset-{nonce}-'):
+                        try:
+                            timestamp = int(role_name.split('-')[-1])
+                            if current_time - timestamp < 86400:  # 24 hours
+                                expired = False
+                                user_id = row['id']
+                                break
+                        except (ValueError, IndexError):
+                            continue
+                
+                if expired or not user_id:
+                    raise AuthError('Password reset link has expired. Please request a new password reset email.', 400)
+                
+                # Return user info (username only for security)
+                cur.execute("SELECT username FROM users WHERE id = %s", (user_id,))
+                user = cur.fetchone()
+                
+                return jsonify({'username': user['username'], 'message': 'Password reset link is valid.'})
+
+        @bp.route('/password-reset/<nonce>', methods=['POST'])
+        @bp.public_endpoint
+        def reset_password(nonce):
+            data = request.get_json()
+            password = data.get('password')
+            confirm_password = data.get('confirmPassword')
+            
+            if not password:
+                raise AuthError('Password is required', 400)
+            if password != confirm_password:
+                raise AuthError('Passwords do not match', 400)
+            
+            with self.db.get_cursor() as cur:
+                # Find user with password-reset-{nonce}-{timestamp} role
+                cur.execute("""
+                    SELECT u.id, u.username, u.email, r.name as role_name
+                    FROM users u
+                    JOIN user_roles ur ON ur.user_id = u.id
+                    JOIN roles r ON ur.role_id = r.id
+                    WHERE r.name LIKE %s
+                """, (f'password-reset-{nonce}-%',))
+                results = cur.fetchall()
+                
+                if not results:
+                    raise AuthError('Invalid or expired password reset link', 400)
+                
+                # Check if expired (24 hours)
+                current_time = int(time.time())
+                user_id = None
+                username = None
+                email = None
+                expired = True
+                
+                for row in results:
+                    role_name = row['role_name']
+                    if role_name.startswith(f'password-reset-{nonce}-'):
+                        try:
+                            timestamp = int(role_name.split('-')[-1])
+                            if current_time - timestamp < 86400:  # 24 hours
+                                expired = False
+                                user_id = row['id']
+                                username = row['username']
+                                email = row['email']
+                                break
+                        except (ValueError, IndexError):
+                            continue
+                
+                if expired or not user_id:
+                    raise AuthError('Password reset link has expired. Please request a new password reset email.', 400)
+                
+                # Validate password strength
+                self._validate_password_strength(password, username=username, email=email)
+                
+                # Hash new password
+                salt = bcrypt.gensalt()
+                password_hash = bcrypt.hashpw(password.encode('utf-8'), salt)
+                
+                # Update user's password
+                cur.execute("""
+                    UPDATE users 
+                    SET password_hash = %s, updated_at = %s
+                    WHERE id = %s
+                """, (password_hash.decode('utf-8'), datetime.utcnow(), user_id))
+                
+                # Remove all password-reset-* roles from user
+                cur.execute("""
+                    DELETE FROM user_roles
+                    WHERE user_id = %s
+                    AND role_id IN (
+                        SELECT id FROM roles WHERE name LIKE 'password-reset-%%'
+                    )
+                """, (user_id,))
+            
+            return jsonify({'message': 'Password has been reset successfully. You can now log in with your new password.'})
 
         @bp.route('/roles', methods=['GET'])
         def get_roles():
@@ -427,6 +995,303 @@ class AuthManager:
                 roles = cur.fetchall()
             return jsonify(roles)
 
+        # Admin endpoints - require administrator role
+        @bp.route('/admin/users', methods=['GET'])
+        def admin_get_users():
+            self._require_admin_role()
+            with self.db.get_cursor() as cur:
+                cur.execute("""
+                    SELECT u.*, 
+                           COALESCE(array_agg(r.name) FILTER (WHERE r.name IS NOT NULL), '{}') as roles
+                    FROM users u
+                    LEFT JOIN user_roles ur ON ur.user_id = u.id
+                    LEFT JOIN roles r ON ur.role_id = r.id
+                    GROUP BY u.id, u.username, u.email, u.real_name, u.created_at, u.updated_at
+                    ORDER BY u.created_at DESC
+                """)
+                users = cur.fetchall()
+            return jsonify(users)
+
+        @bp.route('/admin/users', methods=['POST'])
+        def admin_create_user():
+            self._require_admin_role()
+            data = request.get_json()
+            
+            # Validate required fields
+            required_fields = ['username', 'email', 'real_name', 'password']
+            for field in required_fields:
+                if not data.get(field):
+                    raise AuthError(f'{field} is required', 400)
+            
+            # Validate password strength
+            self._validate_password_strength(data['password'], username=data['username'], email=data['email'])
+            
+            # Hash the password
+            salt = bcrypt.gensalt()
+            password_hash = bcrypt.hashpw(data['password'].encode('utf-8'), salt)
+            
+            with self.db.get_cursor() as cur:
+                # Check if username or email already exists
+                cur.execute("SELECT id FROM users WHERE username = %s OR email = %s", 
+                           (data['username'], data['email']))
+                if cur.fetchone():
+                    raise AuthError('Username or email already exists', 400)
+                
+                # Create user
+                cur.execute("""
+                    INSERT INTO users (username, email, real_name, password_hash, created_at, updated_at)
+                    VALUES (%s, %s, %s, %s, %s, %s)
+                    RETURNING id
+                """, (data['username'], data['email'], data['real_name'], 
+                      password_hash.decode('utf-8'), datetime.utcnow(), datetime.utcnow()))
+                user_id = cur.fetchone()['id']
+                
+                # Assign roles if provided
+                if data.get('roles'):
+                    for role_name in data['roles']:
+                        cur.execute("SELECT id FROM roles WHERE name = %s", (role_name,))
+                        role = cur.fetchone()
+                        if role:
+                            cur.execute("""
+                                INSERT INTO user_roles (user_id, role_id)
+                                VALUES (%s, %s)
+                                ON CONFLICT (user_id, role_id) DO NOTHING
+                            """, (user_id, role['id']))
+            
+            return jsonify({'id': user_id}), 201
+
+        @bp.route('/admin/users/<user_id>', methods=['PUT'])
+        def admin_update_user(user_id):
+            self._require_admin_role()
+            data = request.get_json()
+            
+            with self.db.get_cursor() as cur:
+                # Check if user exists and get current username/email
+                cur.execute("SELECT id, username, email FROM users WHERE id = %s", (user_id,))
+                user = cur.fetchone()
+                if not user:
+                    raise AuthError('User not found', 404)
+                
+                # Get username and email for password validation (use updated values if provided)
+                username = data.get('username', user['username'])
+                email = data.get('email', user['email'])
+                
+                # Validate password strength if password is being updated
+                if 'password' in data:
+                    self._validate_password_strength(data['password'], username=username, email=email)
+                
+                # Update user fields
+                update_fields = []
+                update_values = []
+                
+                if 'username' in data:
+                    update_fields.append('username = %s')
+                    update_values.append(data['username'])
+                if 'email' in data:
+                    update_fields.append('email = %s')
+                    update_values.append(data['email'])
+                if 'real_name' in data:
+                    update_fields.append('real_name = %s')
+                    update_values.append(data['real_name'])
+                if 'password' in data:
+                    salt = bcrypt.gensalt()
+                    password_hash = bcrypt.hashpw(data['password'].encode('utf-8'), salt)
+                    update_fields.append('password_hash = %s')
+                    update_values.append(password_hash.decode('utf-8'))
+                
+                if update_fields:
+                    update_fields.append('updated_at = %s')
+                    update_values.append(datetime.utcnow())
+                    update_values.append(user_id)
+                    
+                    cur.execute(f"""
+                        UPDATE users 
+                        SET {', '.join(update_fields)}
+                        WHERE id = %s
+                    """, update_values)
+                
+                # Update roles if provided
+                if 'roles' in data:
+                    # Remove existing roles
+                    cur.execute("DELETE FROM user_roles WHERE user_id = %s", (user_id,))
+                    
+                    # Add new roles
+                    for role_name in data['roles']:
+                        cur.execute("SELECT id FROM roles WHERE name = %s", (role_name,))
+                        role = cur.fetchone()
+                        if role:
+                            cur.execute("""
+                                INSERT INTO user_roles (user_id, role_id)
+                                VALUES (%s, %s)
+                            """, (user_id, role['id']))
+            
+            return jsonify({'success': True})
+
+        @bp.route('/admin/users/<user_id>', methods=['DELETE'])
+        def admin_delete_user(user_id):
+            self._require_admin_role()
+            
+            with self.db.get_cursor() as cur:
+                # Check if user exists
+                cur.execute("SELECT id FROM users WHERE id = %s", (user_id,))
+                if not cur.fetchone():
+                    raise AuthError('User not found', 404)
+                
+                # Delete user (cascade will handle related records)
+                cur.execute("DELETE FROM users WHERE id = %s", (user_id,))
+            
+            return jsonify({'success': True})
+
+        @bp.route('/admin/roles', methods=['GET'])
+        def admin_get_roles():
+            self._require_admin_role()
+            with self.db.get_cursor() as cur:
+                cur.execute("SELECT * FROM roles ORDER BY name")
+                roles = cur.fetchall()
+            return jsonify(roles)
+
+        @bp.route('/admin/roles', methods=['POST'])
+        def admin_create_role():
+            self._require_admin_role()
+            data = request.get_json()
+            
+            if not data.get('name'):
+                raise AuthError('Role name is required', 400)
+            
+            with self.db.get_cursor() as cur:
+                # Check if role already exists
+                cur.execute("SELECT id FROM roles WHERE name = %s", (data['name'],))
+                if cur.fetchone():
+                    raise AuthError('Role already exists', 400)
+                
+                cur.execute("""
+                    INSERT INTO roles (name, description, created_at)
+                    VALUES (%s, %s, %s)
+                    RETURNING id
+                """, (data['name'], data.get('description', ''), datetime.utcnow()))
+                role_id = cur.fetchone()['id']
+            
+            return jsonify({'id': role_id}), 201
+
+        @bp.route('/admin/roles/<role_id>', methods=['PUT'])
+        def admin_update_role(role_id):
+            self._require_admin_role()
+            data = request.get_json()
+            
+            with self.db.get_cursor() as cur:
+                # Check if role exists
+                cur.execute("SELECT id FROM roles WHERE id = %s", (role_id,))
+                if not cur.fetchone():
+                    raise AuthError('Role not found', 404)
+                
+                update_fields = []
+                update_values = []
+                
+                if 'name' in data:
+                    update_fields.append('name = %s')
+                    update_values.append(data['name'])
+                if 'description' in data:
+                    update_fields.append('description = %s')
+                    update_values.append(data['description'])
+                
+                if update_fields:
+                    update_values.append(role_id)
+                    cur.execute(f"""
+                        UPDATE roles 
+                        SET {', '.join(update_fields)}
+                        WHERE id = %s
+                    """, update_values)
+            
+            return jsonify({'success': True})
+
+        @bp.route('/admin/roles/<role_id>', methods=['DELETE'])
+        def admin_delete_role(role_id):
+            self._require_admin_role()
+            
+            with self.db.get_cursor() as cur:
+                # Check if role exists
+                cur.execute("SELECT id FROM roles WHERE id = %s", (role_id,))
+                if not cur.fetchone():
+                    raise AuthError('Role not found', 404)
+                
+                # Check if role is assigned to any users
+                cur.execute("SELECT COUNT(*) as count FROM user_roles WHERE role_id = %s", (role_id,))
+                count = cur.fetchone()['count']
+                if count > 0:
+                    raise AuthError('Cannot delete role that is assigned to users', 400)
+                
+                cur.execute("DELETE FROM roles WHERE id = %s", (role_id,))
+            
+            return jsonify({'success': True})
+
+        @bp.route('/admin/api-tokens', methods=['GET'])
+        def admin_get_all_tokens():
+            self._require_admin_role()
+            with self.db.get_cursor() as cur:
+                cur.execute("""
+                    SELECT t.*, u.username, u.email
+                    FROM api_tokens t
+                    JOIN users u ON t.user_id = u.id
+                    ORDER BY t.created_at DESC
+                """)
+                tokens = cur.fetchall()
+            return jsonify(tokens)
+
+        @bp.route('/admin/api-tokens', methods=['POST'])
+        def admin_create_token():
+            self._require_admin_role()
+            data = request.get_json()
+            
+            if not data.get('user_id') or not data.get('name'):
+                raise AuthError('user_id and name are required', 400)
+            
+            expires_in_days = data.get('expires_in_days')
+            token = self.create_api_token(data['user_id'], data['name'], expires_in_days)
+            
+            return jsonify({
+                'id': token.id,
+                'name': token.name,
+                'token': token.get_full_token(),
+                'created_at': token.created_at,
+                'expires_at': token.expires_at
+            }), 201
+
+        @bp.route('/admin/api-tokens/<token_id>', methods=['DELETE'])
+        def admin_delete_token(token_id):
+            self._require_admin_role()
+            
+            with self.db.get_cursor() as cur:
+                cur.execute("DELETE FROM api_tokens WHERE id = %s", (token_id,))
+                if cur.rowcount == 0:
+                    raise AuthError('Token not found', 404)
+            
+            return jsonify({'success': True})
+
+        @bp.route('/admin/invite', methods=['POST'])
+        def admin_send_invitation():
+            self._require_admin_role()
+            data = request.get_json()
+            
+            if not data.get('email'):
+                raise AuthError('Email is required', 400)
+            
+            # Check if user already exists
+            with self.db.get_cursor() as cur:
+                cur.execute("SELECT id FROM users WHERE email = %s", (data['email'],))
+                if cur.fetchone():
+                    raise AuthError('User with this email already exists', 400)
+            
+            # Send invitation email (placeholder - implement actual email sending)
+            invitation_token = str(uuid.uuid4())
+            
+            # Store invitation in database (you might want to create an invitations table)
+            # For now, we'll just return success
+            return jsonify({
+                'success': True,
+                'message': f'Invitation sent to {data["email"]}',
+                'invitation_token': invitation_token
+            })
+
         return bp
 
     def validate_token(self, token):
@@ -436,21 +1301,42 @@ class AuthManager:
             logger.debug(f"Token payload: {payload}")
             user_id = int(payload['sub'])  # Convert string ID back to integer
             
+            # Check cache first
+            cache_key = f"user_{user_id}"
+            current_time = datetime.utcnow()
+            
+            if cache_key in self._user_cache:
+                cached_data, cache_time = self._user_cache[cache_key]
+                if (current_time - cache_time).total_seconds() < self._cache_ttl:
+                    logger.debug(f"Returning cached user data for ID: {user_id}")
+                    return cached_data.copy()  # Return a copy to avoid modifying cache
+            
+            # Cache miss or expired, fetch from database
             with self.db.get_cursor() as cur:
-                cur.execute("SELECT * FROM users WHERE id = %s", (user_id,))
-                user = cur.fetchone()
-                if not user:
-                    logger.error(f"User not found for ID: {user_id}")
-                    raise AuthError('User not found', 404)
-                # Fetch roles
                 cur.execute("""
-                    SELECT r.name FROM roles r
-                    JOIN user_roles ur ON ur.role_id = r.id
-                    WHERE ur.user_id = %s
+                    SELECT u.*, r.name as role_name FROM users u
+                    LEFT JOIN user_roles ur ON ur.user_id = u.id
+                    LEFT JOIN roles r ON ur.role_id = r.id
+                    WHERE u.id = %s
                 """, (user_id,))
-                roles = [row['name'] for row in cur.fetchall()]
+                results = cur.fetchall()
+                if not results:
+                    logger.error(f"User not found for ID: {user_id}")
+                    raise AuthError('User not found', 404)
+                
+                # Get the first row for user data (all rows will have same user data)
+                user = results[0]
+                
+                # Extract roles from results
+                roles = [row['role_name'] for row in results if row['role_name'] is not None]
                 user['roles'] = roles
 
+            # Cache the result
+            self._user_cache[cache_key] = (user.copy(), current_time)
+            
+            # Clean up expired cache entries
+            self._cleanup_cache()
+            
             return user
         except jwt.InvalidTokenError as e:
             logger.error(f"Invalid token error: {str(e)}")
@@ -459,9 +1345,87 @@ class AuthManager:
             logger.error(f"Unexpected error during token validation: {str(e)}")
             raise AuthError(str(e), 500)
 
+    def _cleanup_cache(self):
+        """Remove expired cache entries."""
+        current_time = datetime.utcnow()
+        expired_keys = [
+            key for key, (_, cache_time) in self._user_cache.items()
+            if (current_time - cache_time).total_seconds() >= self._cache_ttl
+        ]
+        for key in expired_keys:
+            del self._user_cache[key]
+
+    def _start_update_thread(self):
+        """Start the background thread for processing last_used_at updates."""
+        if self._update_thread is None or not self._update_thread.is_alive():
+            self._update_thread = threading.Thread(target=self._update_worker, daemon=True)
+            self._update_thread.start()
+            logger.debug("Started background update thread")
+
+    def _schedule_last_used_update(self, token_id):
+        """Schedule a last_used_at update for an API token with 10s delay."""
+        with self._update_lock:
+            self._last_used_updates[token_id] = time.time()
+            logger.debug(f"Scheduled last_used update for token {token_id}")
+
+    def _update_worker(self):
+        """Background worker that processes last_used_at updates."""
+        while not self._shutdown_event.is_set():
+            try:
+                current_time = time.time()
+                tokens_to_update = []
+                
+                # Collect tokens that need updating (older than 10 seconds)
+                with self._update_lock:
+                    for token_id, schedule_time in list(self._last_used_updates.items()):
+                        if current_time - schedule_time >= 10:  # 10 second delay
+                            tokens_to_update.append(token_id)
+                            del self._last_used_updates[token_id]
+                
+                # Perform batch update
+                if tokens_to_update:
+                    self._perform_batch_update(tokens_to_update)
+                
+                # Sleep for a short interval
+                time.sleep(10)
+                
+            except Exception as e:
+                logger.error(f"Error in update worker: {e}")
+                time.sleep(5)  # Wait longer on error
+
+    def _perform_batch_update(self, token_ids):
+        """Perform batch update of last_used_at for multiple tokens."""
+        try:
+            with self.db.get_cursor() as cur:
+                # Update all tokens in a single query
+                placeholders = ','.join(['%s'] * len(token_ids))
+                cur.execute(f"""
+                    UPDATE api_tokens 
+                    SET last_used_at = %s
+                    WHERE id IN ({placeholders})
+                """, [datetime.utcnow()] + token_ids)
+                
+                logger.debug(f"Updated last_used_at for {len(token_ids)} tokens: {token_ids}")
+                
+        except Exception as e:
+            logger.error(f"Error performing batch update: {e}")
+
+    def shutdown(self):
+        """Shutdown the background update thread."""
+        self._shutdown_event.set()
+        if self._update_thread and self._update_thread.is_alive():
+            self._update_thread.join(timeout=5)
+            logger.debug("Background update thread shutdown complete")
+
     def get_current_user(self):
         return self._authenticate_request()
 
+    def _require_admin_role(self):
+        """Require the current user to have administrator role."""
+        user = g.requesting_user
+        if not user or 'administrator' not in user.get('roles', []):
+            raise AuthError('Administrator role required', 403)
+
     def get_user_api_tokens(self, user_id):
         """Get all API tokens for a user."""
         with self.db.get_cursor() as cur:
@@ -487,12 +1451,12 @@ class AuthManager:
     def _create_token(self, user):
         payload = {
             'sub': str(user['id']),
-            'exp': datetime.utcnow() + timedelta(hours=1),
+            'exp': datetime.utcnow() + self.expiry_time,
             'iat': datetime.utcnow()
         }
         logger.debug(f"Creating token with payload: {payload}")
         token = jwt.encode(payload, self.jwt_secret, algorithm='HS256')
-        logger.debug(f"Created token: {token}")
+        logger.info(f"Created token: {token}")
         return token
 
     def _create_refresh_token(self, user):
@@ -506,73 +1470,295 @@ class AuthManager:
     def _verify_password(self, password, password_hash):
         return bcrypt.checkpw(password.encode('utf-8'), password_hash.encode('utf-8'))
 
+    def _validate_password_strength(self, password, username=None, email=None):
+        """Validate password strength and return error message listing all rules and failures."""
+        rules = []
+        failures = []
+        
+        # Rule 1: Minimum length
+        min_length = 8
+        rules.append(f"At least {min_length} characters long")
+        if len(password) < min_length:
+            failures.append(f"At least {min_length} characters long")
+        
+        # Rule 2: Maximum length
+        max_length = 128
+        rules.append(f"No more than {max_length} characters long")
+        if len(password) > max_length:
+            failures.append(f"No more than {max_length} characters long")
+        
+        # Rule 3: Uppercase letter
+        rules.append("Contains at least one uppercase letter (A-Z)")
+        if not re.search(r'[A-Z]', password):
+            failures.append("Contains at least one uppercase letter (A-Z)")
+        
+        # Rule 4: Lowercase letter
+        rules.append("Contains at least one lowercase letter (a-z)")
+        if not re.search(r'[a-z]', password):
+            failures.append("Contains at least one lowercase letter (a-z)")
+        
+        # Rule 5: Digit
+        rules.append("Contains at least one number (0-9)")
+        if not re.search(r'\d', password):
+            failures.append("Contains at least one number (0-9)")
+        
+        # Rule 6: Special character
+        rules.append("Contains at least one special character (!@#$%^&*()_+-=[]{}|;:,.<>?)")
+        if not re.search(r'[!@#$%^&*()_+\-=\[\]{}|;:,.<>?]', password):
+            failures.append("Contains at least one special character (!@#$%^&*()_+-=[]{}|;:,.<>?)")
+        
+        # Rule 7: Not contain username
+        if username:
+            rules.append("Does not contain your username")
+            if username.lower() in password.lower():
+                failures.append("Does not contain your username")
+        
+        # Rule 8: Not contain email username
+        if email:
+            email_username = email.split('@')[0].lower()
+            rules.append("Does not contain your email username")
+            if email_username and email_username in password.lower():
+                failures.append("Does not contain your email username")
+        
+        # Rule 9: Not a common password
+        common_passwords = {'password', 'password123', '12345678', 'qwerty', 'abc123', 'letmein', 'welcome', 'monkey', '1234567890', 'password1'}
+        rules.append("Is not a common password")
+        if password.lower() in common_passwords:
+            failures.append("Is not a common password")
+        
+        if failures:
+            all_rules_text = "\n".join([f"  {'✗' if rule in failures else '✓'} {rule}" for rule in rules])
+            error_msg = f"Password does not meet the following requirements:\n\n{all_rules_text}\n\nPlease fix the issues marked with ✗."
+            raise AuthError(error_msg, 400)
+        
+        return True
+
     def _get_oauth_url(self, provider, redirect_uri):
-        if provider == 'google':
-            client_id = self.oauth_config['google']['client_id']
-            scope = 'openid email profile'
-            state = provider  # Pass provider as state for callback
-            return f'https://accounts.google.com/o/oauth2/v2/auth?client_id={client_id}&redirect_uri={redirect_uri}&response_type=code&scope={scope}&state={state}'
-        raise AuthError('Invalid OAuth provider')
+        meta = self._get_provider_meta(provider)
+        client_id = self.oauth_config[provider]['client_id']
+        scope = self.oauth_config[provider].get('scope', meta['default_scope'])
+        state = provider  # Pass provider as state for callback
+        # Some providers require additional params
+        params = {
+            'client_id': client_id,
+            'redirect_uri': redirect_uri,
+            'response_type': 'code',
+            'scope': scope,
+            'state': state
+        }
+        # Facebook requires display; GitHub supports prompt
+        if provider == 'facebook':
+            params['display'] = 'page'
+        # Build URL
+        from urllib.parse import urlencode
+        return f"{meta['auth_url']}?{urlencode(params)}"
 
     def _get_oauth_user_info(self, provider, code):
-        if provider == 'google':
-            client_id = self.oauth_config['google']['client_id']
-            client_secret = self.oauth_config['google']['client_secret']
-            redirect_uri = self.get_redirect_uri()
-
-            # Exchange code for tokens
-            token_url = 'https://oauth2.googleapis.com/token'
+        meta = self._get_provider_meta(provider)
+        client_id = self.oauth_config[provider]['client_id']
+        client_secret = self.oauth_config[provider]['client_secret']
+        redirect_uri = self.get_redirect_uri()
+
+
+        if provider == 'microsoft':
+            import msal
+            client = msal.ConfidentialClientApplication(
+                client_id, 
+                client_credential=client_secret, 
+                authority="https://login.microsoftonline.com/common"
+            )
+            tokens = client.acquire_token_by_authorization_code(
+                code, 
+                scopes=["email"], 
+                redirect_uri=redirect_uri
+            )
+        else:
+            # Standard OAuth flow for other providers
             token_data = {
                 'client_id': client_id,
                 'client_secret': client_secret,
                 'code': code,
                 'grant_type': 'authorization_code',
-                'redirect_uri': redirect_uri
+                'redirect_uri': redirect_uri,
+                'scope': meta['default_scope']
             }
-            token_response = requests.post(token_url, data=token_data)
+            token_headers = {}
+            if provider == 'github':
+                token_headers['Accept'] = 'application/json'
+            token_response = requests.post(meta['token_url'], data=token_data, headers=token_headers)
             logger.info("TOKEN RESPONSE: {} {} {} [[[{}]]]".format(token_response.text, token_response.status_code, token_response.headers, token_data))
             token_response.raise_for_status()
             tokens = token_response.json()
 
-            # Get user info
-            userinfo_url = 'https://www.googleapis.com/oauth2/v3/userinfo'
-            userinfo_response = requests.get(
-                userinfo_url,
-                headers={'Authorization': f"Bearer {tokens['access_token']}"}
-            )
-            userinfo_response.raise_for_status()
-            userinfo = userinfo_response.json()
 
-            # Create or update user
-            with self.db.get_cursor() as cur:
-                cur.execute("SELECT * FROM users WHERE email = %s", (userinfo['email'],))
-                user = cur.fetchone()
+        access_token = tokens.get('access_token') or tokens.get('id_token')
+        if not access_token:
+            # Some providers return id_token separately but require access_token for userinfo
+            access_token = tokens.get('access_token')
 
-                if not user:
-                    # Create new user
-                    user = User(
-                        username=userinfo['email'],
-                        email=userinfo['email'],
-                        real_name=userinfo.get('name', userinfo['email']),
-                        id_generator=self.db.get_id_generator()
-                    )
-                    cur.execute("""
-                        INSERT INTO users (username, email, real_name, created_at, updated_at)
-                        VALUES (%s, %s, %s, %s, %s)
-                        RETURNING id
-                    """, (user.username, user.email, user.real_name, 
-                          user.created_at, user.updated_at))
-                    user.id = cur.fetchone()['id']
-                    user = {'id': user.id, 'username': user.username, 'email': user.email, 
-                           'real_name': user.real_name, 'roles': []}
-                else:
-                    # Update existing user
-                    cur.execute("""
-                        UPDATE users 
-                        SET real_name = %s, updated_at = %s
-                        WHERE email = %s
-                    """, (userinfo.get('name', userinfo['email']), datetime.utcnow(), userinfo['email']))
-                    user['real_name'] = userinfo.get('name', userinfo['email'])
+        # Build userinfo request
+        userinfo_url = meta['userinfo_url']
+        userinfo_headers = {'Authorization': f"Bearer {access_token}"}
+        if provider == 'facebook':
+            # Ensure fields
+            from urllib.parse import urlencode
+            userinfo_url = f"{userinfo_url}?{urlencode({'fields': 'id,name,email'})}"
 
-            return user
-        raise AuthError('Invalid OAuth provider') 
+        userinfo_response = requests.get(userinfo_url, headers=userinfo_headers)
+        userinfo_response.raise_for_status()
+        raw_userinfo = userinfo_response.json()
+
+        # Special handling for GitHub missing email
+        if provider == 'github' and not raw_userinfo.get('email'):
+            emails_resp = requests.get('https://api.github.com/user/emails', headers={**userinfo_headers, 'Accept': 'application/vnd.github+json'})
+            if emails_resp.ok:
+                emails = emails_resp.json()
+                primary = next((e for e in emails if e.get('primary') and e.get('verified')), None)
+                raw_userinfo['email'] = (primary or (emails[0] if emails else {})).get('email')
+
+
+
+
+        # Normalize
+        norm = self._normalize_userinfo(provider, raw_userinfo)
+        if not norm.get('email'):
+            # Fallback pseudo-email if allowed
+            norm['email'] = f"{norm['sub']}@{provider}.local"
+
+        # Create or update user
+        with self.db.get_cursor() as cur:
+            cur.execute("SELECT * FROM users WHERE email = %s", (norm['email'],))
+            user = cur.fetchone()
+
+            if not user:
+                if not self.allow_oauth_auto_create:
+                    raise AuthError('User not found and auto-create disabled', 403)
+                # Create new user (auto-create enabled)
+                user_obj = User(
+                    username=norm['email'],
+                    email=norm['email'],
+                    real_name=norm.get('name', norm['email']),
+                    id_generator=self.db.get_id_generator()
+                )
+                cur.execute("""
+                    INSERT INTO users (username, email, real_name, created_at, updated_at)
+                    VALUES (%s, %s, %s, %s, %s)
+                    RETURNING id
+                """, (user_obj.username, user_obj.email, user_obj.real_name, 
+                      user_obj.created_at, user_obj.updated_at))
+                new_id = cur.fetchone()['id']
+                user = {'id': new_id, 'username': user_obj.username, 'email': user_obj.email, 
+                        'real_name': user_obj.real_name, 'roles': []}
+            else:
+                # Update existing user
+                cur.execute("""
+                    UPDATE users 
+                    SET real_name = %s, updated_at = %s
+                    WHERE email = %s
+                """, (norm.get('name', norm['email']), datetime.utcnow(), norm['email']))
+                user['real_name'] = norm.get('name', norm['email'])
+
+        return user
+
+    def _get_provider_meta(self, provider):
+        providers = {
+            'google': {
+                'auth_url': 'https://accounts.google.com/o/oauth2/v2/auth',
+                'token_url': 'https://oauth2.googleapis.com/token',
+                'userinfo_url': 'https://www.googleapis.com/oauth2/v3/userinfo',
+                'default_scope': 'openid email profile'
+            },
+            'github': {
+                'auth_url': 'https://github.com/login/oauth/authorize',
+                'token_url': 'https://github.com/login/oauth/access_token',
+                'userinfo_url': 'https://api.github.com/user',
+                'default_scope': 'read:user user:email'
+            },
+            'facebook': {
+                'auth_url': 'https://www.facebook.com/v11.0/dialog/oauth',
+                'token_url': 'https://graph.facebook.com/v11.0/oauth/access_token',
+                'userinfo_url': 'https://graph.facebook.com/me',
+                'default_scope': 'email public_profile'
+            },
+            'microsoft': {
+                'auth_url': 'https://login.microsoftonline.com/common/oauth2/v2.0/authorize',
+                'token_url': 'https://login.microsoftonline.com/common/oauth2/v2.0/token',
+                'userinfo_url': 'https://graph.microsoft.com/oidc/userinfo',
+                'default_scope': 'openid email profile'
+            },
+            'linkedin': {
+                'auth_url': 'https://www.linkedin.com/oauth/v2/authorization',
+                'token_url': 'https://www.linkedin.com/oauth/v2/accessToken',
+                'userinfo_url': 'https://api.linkedin.com/v2/userinfo',
+                'default_scope': 'openid profile email'
+            },
+            'slack': {
+                'auth_url': 'https://slack.com/openid/connect/authorize',
+                'token_url': 'https://slack.com/api/openid.connect.token',
+                'userinfo_url': 'https://slack.com/api/openid.connect.userInfo',
+                'default_scope': 'openid profile email'
+            },
+            'apple': {
+                'auth_url': 'https://appleid.apple.com/auth/authorize',
+                'token_url': 'https://appleid.apple.com/auth/token',
+                'userinfo_url': 'https://appleid.apple.com/auth/userinfo',
+                'default_scope': 'name email'
+            }
+        }
+        if provider not in providers:
+            raise AuthError('Invalid OAuth provider ' + provider)
+        return providers[provider]
+
+    def _normalize_userinfo(self, provider, info):
+        # Map into a common structure: sub, email, name
+        if provider == 'google':
+            return {'sub': info.get('sub'), 'email': info.get('email'), 'name': info.get('name')}
+        if provider == 'github':
+            return {'sub': str(info.get('id')), 'email': info.get('email'), 'name': info.get('name') or info.get('login')}
+        if provider == 'facebook':
+            return {'sub': info.get('id'), 'email': info.get('email'), 'name': info.get('name')}
+        if provider == 'microsoft':
+            # OIDC userinfo
+            return {'sub': info.get('sub') or info.get('oid'), 'email': info.get('email') or info.get('preferred_username'), 'name': info.get('name')}
+        if provider == 'linkedin':
+            return {'sub': info.get('sub') or info.get('id'), 'email': info.get('email'), 'name': info.get('name')}
+        if provider == 'slack':
+            return {'sub': info.get('sub'), 'email': info.get('email'), 'name': info.get('name')}
+        if provider == 'apple':
+            # Apple email may be private relay; name not always present
+            return {'sub': info.get('sub'), 'email': info.get('email'), 'name': info.get('name')}
+        return {'sub': info.get('sub'), 'email': info.get('email'), 'name': info.get('name')}
+    
+    def _send_email(self, to_email, subject, body):
+        if not self.email_server or not self.email_username or not self.email_password:
+            logger.error('Email configuration not set, cannot send email')
+            raise AuthError('Email configuration not set. Cannot send validation email.', 500)
+        
+        try:
+            msg = MIMEMultipart()
+            msg['From'] = self.email_address
+            msg['To'] = to_email
+            msg['Reply-To'] = self.email_reply_to
+            msg['Subject'] = subject
+            msg.attach(MIMEText(body, 'plain'))
+            
+            server = smtplib.SMTP(self.email_server, self.email_port)
+            server.starttls()
+            server.login(self.email_username, self.email_password)
+            server.send_message(msg)
+            server.quit()
+            logger.info(f'Validation email sent to {to_email}')
+        except AuthError:
+            raise
+        except Exception as e:
+            logger.error(f'Failed to send email to {to_email}: {e}')
+            raise AuthError(f'Failed to send validation email: {str(e)}', 500)
+    
+    def _get_frontend_url(self):
+        frontend_url = os.getenv('FRONTEND_URL')
+        if not frontend_url:
+            from urllib.parse import urlparse, urlunparse
+            redirect_uri = self.get_redirect_uri()
+            parsed_uri = urlparse(redirect_uri)
+            frontend_url = urlunparse((parsed_uri.scheme, parsed_uri.netloc, '', '', '', ''))
+        return frontend_url