feat: Enhance email templates and add plain text support for improved deliverability

TODO.md

@@ -55,10 +55,10 @@ This document outlines upcoming tasks and improvements for the LeagueLedger appl
 ## User Management & Profile Features
 
 - [ ] **Profile Management**
-  - [ ] Update profile picture functionality
+  - [x] Update profile picture functionality
-  - [ ] Change username capability
+  - [x] Change username capability
-  - [ ] Account deletion process
+  - [x] Account deletion process
-  - [ ] Profile privacy settings
+  - [x] Profile privacy settings
   - [ ] Social media integration
 
 ## Environment Variables & Configuration
@@ -158,4 +158,10 @@ This document outlines upcoming tasks and improvements for the LeagueLedger appl
 - [ ] Create database migration tools
 - [ ] Add support for clustering/high availability
 - [ ] Implement CDN for static assets
-- [ ] Create backup and disaster recovery procedures
+- [ ] Create backup and disaster recovery procedures
+
+
+## Layout
+- [ ] Change layout to use Tailwind CSS
+- [ ] Change layout to use https://ui.shadcn.com/
+- [ ] Make mail templates less spam-y

app/db_init.py

@@ -8,6 +8,7 @@ from datetime import datetime, timedelta
 from sqlalchemy import inspect
 from sqlalchemy.orm import Session
 from passlib.context import CryptContext
+import asyncio
 
 from .models import User, Team, TeamMembership, QRCode, QRSet, TeamAchievement, Event, SystemSettings
 from .db import SessionLocal, engine
@@ -26,17 +27,17 @@ def table_has_column(engine, table_name, column_name):
     columns = [col['name'] for col in inspector.get_columns(table_name)]
     return column_name in columns
 
-def init_db():
+async def init_db():
     """Initialize the database, applying migrations and seeding data."""
     # First, create all tables if they don't exist
     from .models import Base
     Base.metadata.create_all(bind=engine)
     # Then, run any needed migrations
-    run_migrations(engine)
+    await asyncio.to_thread(run_migrations, engine)
     # Then proceed with seeding if needed
-    seed_db()
+    await asyncio.to_thread(seed_db)
     # Initialize system settings if needed
-    init_system_settings()
+    await asyncio.to_thread(init_system_settings)
 
 def init_system_settings():
     """Initialize the system settings table if it doesn't exist."""
@@ -173,23 +174,24 @@ def seed_db():
         memberships = []
         membership_data = [
             # Quiz Wizards
-            (1, 1, True, 160),  # Admin user is team admin of Quiz Wizards
+            (1, 1, True, True, 160),  # Admin user is team admin AND captain of Quiz Wizards
-            (2, 1, True, 155),
+            (2, 1, True, True, 155),  # John is also admin AND captain
-            (3, 1, False, 130),
+            (3, 1, False, False, 130),
-            (4, 1, False, 90),
+            (4, 1, False, False, 90),
-            (5, 1, False, 45),
+            (5, 1, False, False, 45),
             # Trivia Titans
-            (2, 2, True, 150),
+            (2, 2, True, True, 150),  # John is admin AND captain of Trivia Titans
-            (1, 2, False, 145),
+            (1, 2, False, False, 145),
             # Beer Brainiacs
-            (3, 3, True, 120),
+            (3, 3, True, True, 120),  # Sarah is admin AND captain of Beer Brainiacs
         ]
         
-        for user_id, team_id, is_admin, days_ago in membership_data:
+        for user_id, team_id, is_admin, is_captain, days_ago in membership_data:
             membership_attrs = {
                 "user_id": user_id,
                 "team_id": team_id,
-                "is_admin": is_admin
+                "is_admin": is_admin,
+                "is_captain": is_captain  # Added is_captain field
             }
             if has_joined_at:
                 membership_attrs["joined_at"] = datetime.now() - timedelta(days=days_ago)
@@ -366,4 +368,4 @@ def seed_db():
         db.close()
 
 if __name__ == "__main__":
-    init_db()
+    asyncio.run(init_db())

app/main.py

@@ -11,6 +11,11 @@ from starlette.middleware.authentication import AuthenticationMiddleware
 from dotenv import load_dotenv
 import logging
 import contextlib
+import time
+import asyncio
+import sqlalchemy
+from sqlalchemy.exc import OperationalError, ProgrammingError
+from sqlalchemy import text
 
 from .db import engine, get_db
 from . import models
@@ -52,10 +57,54 @@ app.add_middleware(
 # Then add SessionMiddleware (last added = first executed)
 app.add_middleware(SessionMiddleware, secret_key=SECRET_KEY)
 
-# Initialize database on startup
+# Function to check database connection
-@app.on_event("startup")
+async def check_db_connection(max_retries=10, initial_retry_delay=1):
-async def startup_db_client():
+    """
-    logger.info("Starting database initialization")
+    Check database connection with retries and exponential backoff
+    
+    Args:
+        max_retries: Maximum number of retry attempts
+        initial_retry_delay: Initial delay before first retry in seconds
+        
+    Returns:
+        bool: True if connection succeeded, False otherwise
+    """
+    retry_delay = initial_retry_delay
+    
+    for attempt in range(1, max_retries + 1):
+        try:
+            # Try a simple query to test the connection
+            with engine.connect() as conn:
+                conn.execute(text("SELECT 1"))
+                logger.info(f"Database connection successful on attempt {attempt}")
+                return True
+        except (OperationalError, ProgrammingError) as e:
+            if "Connection refused" in str(e) or "Can't connect" in str(e):
+                logger.warning(f"Database connection attempt {attempt}/{max_retries} failed: {str(e)}")
+                
+                if attempt < max_retries:
+                    logger.info(f"Retrying in {retry_delay} seconds...")
+                    await asyncio.sleep(retry_delay)
+                    # Exponential backoff with a maximum delay of 10 seconds
+                    retry_delay = min(retry_delay * 2, 10)
+                else:
+                    logger.error(f"Failed to connect to database after {max_retries} attempts")
+                    return False
+            else:
+                # For other database errors, log and continue
+                logger.error(f"Database error: {str(e)}")
+                return False
+        except Exception as e:
+            logger.error(f"Unexpected error connecting to database: {str(e)}")
+            return False
+            
+    return False
+
+# Initialize database with schema and tables
+async def initialize_database():
+    """
+    Initialize the database schema and seed data
+    """
     try:
         # Import models to ensure they're registered with Base before initialization
         from . import models
@@ -63,10 +112,29 @@ async def startup_db_client():
         # Initialize database (applies migrations and seeds data)
         init_db()
         logger.info("Database initialized and migrated successfully")
-            
+        return True
     except Exception as e:
         logger.error(f"Database initialization error: {str(e)}")
-        # We continue even if there was an error, as the application might still work with partial functionality
+        return False
+
+# Initialize database on startup
+@app.on_event("startup")
+async def startup_db_client():
+    logger.info("Starting database initialization")
+    
+    # First, ensure database server is available with polling
+    max_retries = 15  # Try up to 15 times (with exponential backoff, this could be ~2 minutes)
+    connected = await check_db_connection(max_retries=max_retries)
+    
+    if connected:
+        # Once connected, initialize the database
+        success = await initialize_database()
+        if success:
+            logger.info("Database setup completed successfully")
+        else:
+            logger.warning("Database initialization completed with errors")
+    else:
+        logger.error("Failed to connect to database, application may not function correctly")
 
 # Mount static files
 app.mount("/static", StaticFiles(directory="app/static"), name="static")

app/templates/email/email_verification.html

@@ -12,62 +12,92 @@
             max-width: 600px;
             margin: 0 auto;
             padding: 20px;
+            background-color: #f9f9f9;
+        }
+        .container {
+            background-color: #ffffff;
+            border-radius: 8px;
+            box-shadow: 0 2px 4px rgba(0,0,0,0.1);
+            overflow: hidden;
         }
         .header {
             background-color: #2D7738;
             padding: 20px;
             text-align: center;
             color: white;
-            border-radius: 5px 5px 0 0;
         }
         .content {
-            padding: 20px;
+            padding: 30px;
-            border: 1px solid #ddd;
+            background-color: #ffffff;
-            border-top: none;
+        }
-            border-radius: 0 0 5px 5px;
+        .button-container {
+            margin: 25px 0;
+            text-align: center;
         }
         .button {
             display: inline-block;
             background-color: #2D7738;
             color: white;
             text-decoration: none;
-            padding: 10px 20px;
+            padding: 12px 25px;
             border-radius: 5px;
-            margin: 20px 0;
+            font-weight: 500;
+        }
+        .link-help {
+            margin-top: 20px;
+            padding: 15px;
+            background-color: #f5f5f5;
+            border-radius: 5px;
+            font-size: 14px;
         }
         .footer {
-            margin-top: 20px;
+            padding: 20px;
-            font-size: 12px;
             text-align: center;
+            font-size: 12px;
             color: #777;
+            border-top: 1px solid #eaeaea;
         }
     </style>
 </head>
 <body>
-    <div class="header">
+    <div class="container">
-        <h1>Verify Your Email Address</h1>
+        <div class="header">
-    </div>
+            <h1>Email Verification</h1>
-    
+        </div>
-    <div class="content">
-        <p>Hello {{ username }},</p>
         
-        <p>Thank you for registering with LeagueLedger! To complete your registration, please verify your email address by clicking the button below:</p>
+        <div class="content">
+            <p>Hello {{ username }},</p>
+            
+            <p>Thank you for creating an account with LeagueLedger, your pub quiz team tracking platform. We're excited to have you join our community!</p>
+            
+            <p>To ensure account security and complete your registration, please verify your email address by clicking the button below:</p>
+            
+            <div class="button-container">
+                <a href="{{ verification_link }}" class="button">Verify My Email</a>
+            </div>
+            
+            <div class="link-help">
+                <p>If the button above doesn't work, you can copy and paste this link into your browser:</p>
+                <p><a href="{{ verification_link }}">Complete your verification</a></p>
+            </div>
+            
+            <p>This verification step helps us keep your account secure and allows you to:</p>
+            <ul>
+                <li>Create or join teams</li>
+                <li>Track your quiz night scores</li>
+                <li>Earn points and achievements</li>
+                <li>Climb the leaderboards</li>
+            </ul>
+            
+            <p>If you did not create an account with LeagueLedger, please disregard this email.</p>
+            
+            <p>Best regards,<br>The LeagueLedger Team</p>
+        </div>
         
-        <p style="text-align: center;">
+        <div class="footer">
-            <a href="{{ verification_link }}" class="button">Verify Email</a>
+            <p>© 2025 LeagueLedger. All rights reserved.</p>
-        </p>
+            <p>This email was sent to verify your account registration.</p>
-        
+        </div>
-        <p>Or copy and paste this link into your browser:</p>
-        <p>{{ verification_link }}</p>
-        
-        <p>If you did not create an account with us, please ignore this email.</p>
-        
-        <p>Best regards,<br>The LeagueLedger Team</p>
-    </div>
-    
-    <div class="footer">
-        <p>© LeagueLedger. All rights reserved.</p>
-        <p>This is an automated message, please do not reply to this email.</p>
     </div>
 </body>
 </html>

app/templates/email/join_request_response.html

@@ -3,7 +3,7 @@
 <head>
     <meta charset="UTF-8">
     <meta name="viewport" content="width=device-width, initial-scale=1.0">
-    <title>Team Join Request Response - LeagueLedger</title>
+    <title>Team Join Request Update - LeagueLedger</title>
     <style>
         body {
             font-family: Arial, sans-serif;
@@ -12,63 +12,119 @@
             max-width: 600px;
             margin: 0 auto;
             padding: 20px;
+            background-color: #f9f9f9;
+        }
+        .container {
+            background-color: #ffffff;
+            border-radius: 8px;
+            box-shadow: 0 2px 4px rgba(0,0,0,0.1);
+            overflow: hidden;
         }
         .header {
             background-color: #2D7738;
             padding: 20px;
             text-align: center;
             color: white;
-            border-radius: 5px 5px 0 0;
         }
         .content {
-            padding: 20px;
+            padding: 30px;
-            border: 1px solid #ddd;
+            background-color: #ffffff;
-            border-top: none;
+        }
-            border-radius: 0 0 5px 5px;
+        .status-message {
+            margin: 20px 0;
+            padding: 15px;
+            border-radius: 5px;
+        }
+        .status-approved {
+            background-color: #e8f5e9;
+            border-left: 4px solid #2D7738;
+        }
+        .status-denied {
+            background-color: #f5f5f5;
+            border-left: 4px solid #9e9e9e;
+        }
+        .button-container {
+            margin: 25px 0;
+            text-align: center;
         }
         .button {
             display: inline-block;
             background-color: #2D7738;
             color: white;
             text-decoration: none;
-            padding: 10px 20px;
+            padding: 12px 25px;
+            border-radius: 5px;
+            font-weight: 500;
+        }
+        .next-steps {
+            margin-top: 20px;
+            padding: 15px;
+            background-color: #f5f5f5;
             border-radius: 5px;
-            margin: 20px 0;
         }
         .footer {
-            margin-top: 20px;
+            padding: 20px;
-            font-size: 12px;
             text-align: center;
+            font-size: 12px;
             color: #777;
+            border-top: 1px solid #eaeaea;
         }
     </style>
 </head>
 <body>
-    <div class="header">
+    <div class="container">
-        <h1>Team Join Request {{ "Approved" if is_approved else "Denied" }}</h1>
+        <div class="header">
-    </div>
+            <h1>Team Request {{ "Approved" if is_approved else "Status Update" }}</h1>
-    
+        </div>
-    <div class="content">
-        <p>Hello {{ username }},</p>
         
-        {% if is_approved %}
+        <div class="content">
-        <p>Good news! Your request to join <strong>{{ team_name }}</strong> has been approved. You are now a member of the team.</p>
+            <p>Hello {{ username }},</p>
-        {% else %}
+            
-        <p>We regret to inform you that your request to join <strong>{{ team_name }}</strong> has been denied.</p>
+            {% if is_approved %}
-        {% endif %}
+            <div class="status-message status-approved">
+                <h2>Welcome to the team!</h2>
+                <p>Your request to join <strong>{{ team_name }}</strong> has been approved. You are now officially a member of the team.</p>
+            </div>
+            
+            <p>As a team member, you can now:</p>
+            <ul>
+                <li>Participate in team events</li>
+                <li>Contribute to your team's score</li>
+                <li>Earn points and achievements together</li>
+                <li>Track your team's performance on the leaderboard</li>
+            </ul>
+            
+            <p>Visit your dashboard to see your team's upcoming events and current standings.</p>
+            {% else %}
+            <div class="status-message status-denied">
+                <p>Your request to join <strong>{{ team_name }}</strong> has not been approved at this time.</p>
+                <p>Don't worry - there are many teams in LeagueLedger that might be a better fit for you.</p>
+            </div>
+            
+            <div class="next-steps">
+                <h3>What's next?</h3>
+                <p>You can:</p>
+                <ul>
+                    <li>Request to join another team</li>
+                    <li>Create your own team</li>
+                    <li>Explore upcoming pub quiz events in your area</li>
+                </ul>
+            </div>
+            {% endif %}
+            
+            <div class="button-container">
+                <a href="{{ base_url }}/dashboard" class="button">Go to My Dashboard</a>
+            </div>
+            
+            <p>Thank you for being part of the LeagueLedger community!</p>
+            
+            <p>Best regards,<br>The LeagueLedger Team</p>
+        </div>
         
-        <p>You can view your teams by visiting your dashboard:</p>
+        <div class="footer">
-        
+            <p>© 2025 LeagueLedger. All rights reserved.</p>
-        <p style="text-align: center;">
+            <p>This email was sent to update you about your team join request.</p>
-            <a href="{{ base_url }}/dashboard" class="button">Go to Dashboard</a>
+        </div>
-        </p>
-        
-        <p>Best regards,<br>The LeagueLedger Team</p>
-    </div>
-    
-    <div class="footer">
-        <p>© LeagueLedger. All rights reserved.</p>
-        <p>This is an automated message, please do not reply to this email.</p>
     </div>
 </body>
 </html>

app/templates/email/password_reset.html

@@ -12,64 +12,99 @@
             max-width: 600px;
             margin: 0 auto;
             padding: 20px;
+            background-color: #f9f9f9;
+        }
+        .container {
+            background-color: #ffffff;
+            border-radius: 8px;
+            box-shadow: 0 2px 4px rgba(0,0,0,0.1);
+            overflow: hidden;
         }
         .header {
             background-color: #2D7738;
             padding: 20px;
             text-align: center;
             color: white;
-            border-radius: 5px 5px 0 0;
         }
         .content {
-            padding: 20px;
+            padding: 30px;
-            border: 1px solid #ddd;
+            background-color: #ffffff;
-            border-top: none;
+        }
-            border-radius: 0 0 5px 5px;
+        .security-note {
+            padding: 15px;
+            margin: 20px 0;
+            background-color: #fff8e1;
+            border-left: 3px solid #ffd54f;
+            border-radius: 5px;
+        }
+        .button-container {
+            margin: 25px 0;
+            text-align: center;
         }
         .button {
             display: inline-block;
             background-color: #2D7738;
             color: white;
             text-decoration: none;
-            padding: 10px 20px;
+            padding: 12px 25px;
             border-radius: 5px;
-            margin: 20px 0;
+            font-weight: 500;
+        }
+        .link-help {
+            margin-top: 20px;
+            padding: 15px;
+            background-color: #f5f5f5;
+            border-radius: 5px;
+            font-size: 14px;
         }
         .footer {
-            margin-top: 20px;
+            padding: 20px;
-            font-size: 12px;
             text-align: center;
+            font-size: 12px;
             color: #777;
+            border-top: 1px solid #eaeaea;
         }
     </style>
 </head>
 <body>
-    <div class="header">
+    <div class="container">
-        <h1>Password Reset</h1>
+        <div class="header">
-    </div>
+            <h1>Password Reset</h1>
-    
-    <div class="content">
-        <p>Hello {{ username }},</p>
-        
-        <p>We received a request to reset your password. If you didn't make this request, you can safely ignore this email.</p>
-        
-        <p>To reset your password, click the button below:</p>
-        
-        <div style="margin: 30px 0; text-align: center;">
-            <a href="{{ reset_url }}" class="button">Reset Password</a>
         </div>
         
-        <p>Or you can copy and paste this link into your browser:</p>
+        <div class="content">
-        <p>{{ reset_url }}</p>
+            <p>Hello {{ username }},</p>
+            
+            <p>We received a request to reset your password for your LeagueLedger account. You can set a new password by clicking the button below:</p>
+            
+            <div class="button-container">
+                <a href="{{ reset_url }}" class="button">Reset My Password</a>
+            </div>
+            
+            <div class="security-note">
+                <p><strong>Security Note:</strong> This link will expire in 24 hours for your protection. If you did not request a password reset, please disregard this email and consider reviewing your account security.</p>
+            </div>
+            
+            <div class="link-help">
+                <p>If the button above doesn't work, you can copy and paste this link into your browser:</p>
+                <p><a href="{{ reset_url }}">Reset your password</a></p>
+            </div>
+            
+            <p>With LeagueLedger, you can continue to:</p>
+            <ul>
+                <li>Track your team's progress in pub quiz events</li>
+                <li>View your rank on the leaderboard</li>
+                <li>Manage your team memberships</li>
+                <li>Redeem QR codes for points</li>
+            </ul>
+            
+            <p>Best regards,<br>The LeagueLedger Team</p>
+        </div>
         
-        <p>This link will expire in 24 hours.</p>
+        <div class="footer">
-        
+            <p>© 2025 LeagueLedger. All rights reserved.</p>
-        <p>Best regards,<br>The LeagueLedger Team</p>
+            <p>This email was sent in response to your password reset request.</p>
-    </div>
+        </div>
-    
-    <div class="footer">
-        <p>© LeagueLedger. All rights reserved.</p>
-        <p>This is an automated message, please do not reply to this email.</p>
     </div>
 </body>
 </html>

app/templates/email/team_join_request.html

@@ -12,19 +12,27 @@
             max-width: 600px;
             margin: 0 auto;
             padding: 20px;
+            background-color: #f9f9f9;
+        }
+        .container {
+            background-color: #ffffff;
+            border-radius: 8px;
+            box-shadow: 0 2px 4px rgba(0,0,0,0.1);
+            overflow: hidden;
         }
         .header {
             background-color: #2D7738;
             padding: 20px;
             text-align: center;
             color: white;
-            border-radius: 5px 5px 0 0;
         }
         .content {
-            padding: 20px;
+            padding: 30px;
-            border: 1px solid #ddd;
+            background-color: #ffffff;
-            border-top: none;
+        }
-            border-radius: 0 0 5px 5px;
+        .button-container {
+            margin: 25px 0;
+            text-align: center;
         }
         .button {
             display: inline-block;
@@ -33,54 +41,78 @@
             text-decoration: none;
             padding: 10px 20px;
             border-radius: 5px;
-            margin: 20px 0;
+            font-weight: 500;
         }
         .button.approve {
-            background-color: #4CAF50;
+            background-color: #2D7738;
         }
         .button.deny {
-            background-color: #f44336;
+            background-color: #9e9e9e;
             margin-left: 10px;
         }
-        .footer {
+        .link-help {
             margin-top: 20px;
-            font-size: 12px;
+            padding: 15px;
+            background-color: #f5f5f5;
+            border-radius: 5px;
+            font-size: 14px;
+        }
+        .footer {
+            padding: 20px;
             text-align: center;
+            font-size: 12px;
             color: #777;
+            border-top: 1px solid #eaeaea;
+        }
+        .message-box {
+            margin: 15px 0;
+            padding: 15px;
+            background-color: #f5f5f5;
+            border-radius: 5px;
+            border-left: 3px solid #2D7738;
         }
     </style>
 </head>
 <body>
-    <div class="header">
+    <div class="container">
-        <h1>Team Join Request</h1>
+        <div class="header">
-    </div>
+            <h1>Team Join Request</h1>
-    
-    <div class="content">
-        <p>Hello {{ captain_name }},</p>
-        
-        <p><strong>{{ requester_name }}</strong> has requested to join your team <strong>{{ team_name }}</strong>.</p>
-        
-        {% if message %}
-        <p>Message from {{ requester_name }}:<br><em>"{{ message }}"</em></p>
-        {% endif %}
-        
-        <p>You can approve or deny this request by clicking one of the buttons below:</p>
-        
-        <div style="margin: 30px 0; text-align: center;">
-            <a href="{{ approve_url }}" class="button approve">Approve Request</a>
-            <a href="{{ deny_url }}" class="button deny">Deny Request</a>
         </div>
         
-        <p>Or you can copy and paste one of these links into your browser:</p>
+        <div class="content">
-        <p>Approve: {{ approve_url }}</p>
+            <p>Hello {{ captain_name }},</p>
-        <p>Deny: {{ deny_url }}</p>
+            
+            <p>We hope this email finds you well. <strong>{{ requester_name }}</strong> has requested to join your team <strong>{{ team_name }}</strong> on LeagueLedger.</p>
+            
+            {% if message %}
+            <div class="message-box">
+                <p><strong>Message from {{ requester_name }}:</strong></p>
+                <p><em>"{{ message }}"</em></p>
+            </div>
+            {% endif %}
+            
+            <p>As the team captain, you can review this request and decide whether to approve or deny it.</p>
+            
+            <div class="button-container">
+                <a href="{{ approve_url }}" class="button approve">Approve Request</a>
+                <a href="{{ deny_url }}" class="button deny">Decline Request</a>
+            </div>
+            
+            <div class="link-help">
+                <p>If the buttons above don't work, you can copy and paste one of these links into your browser:</p>
+                <p>To approve: <a href="{{ approve_url }}">Accept team member</a></p>
+                <p>To decline: <a href="{{ deny_url }}">Decline request</a></p>
+            </div>
+            
+            <p>Thank you for being an active team captain in our community!</p>
+            
+            <p>Best regards,<br>The LeagueLedger Team</p>
+        </div>
         
-        <p>Best regards,<br>The LeagueLedger Team</p>
+        <div class="footer">
-    </div>
+            <p>© 2025 LeagueLedger. All rights reserved.</p>
-    
+            <p>This message was sent regarding team management in your LeagueLedger account.</p>
-    <div class="footer">
+        </div>
-        <p>© LeagueLedger. All rights reserved.</p>
-        <p>This is an automated message, please do not reply to this email.</p>
     </div>
 </body>
 </html>

app/templates/email/welcome.html

@@ -12,67 +12,101 @@
             max-width: 600px;
             margin: 0 auto;
             padding: 20px;
+            background-color: #f9f9f9;
+        }
+        .container {
+            background-color: #ffffff;
+            border-radius: 8px;
+            box-shadow: 0 2px 4px rgba(0,0,0,0.1);
+            overflow: hidden;
         }
         .header {
             background-color: #2D7738;
-            padding: 20px;
+            padding: 25px;
             text-align: center;
             color: white;
-            border-radius: 5px 5px 0 0;
         }
         .content {
+            padding: 30px;
+            background-color: #ffffff;
+        }
+        .feature-list {
+            background-color: #f5f5f5;
             padding: 20px;
-            border: 1px solid #ddd;
+            margin: 20px 0;
-            border-top: none;
+            border-radius: 8px;
-            border-radius: 0 0 5px 5px;
+        }
+        .button-container {
+            margin: 25px 0;
+            text-align: center;
         }
         .button {
             display: inline-block;
             background-color: #2D7738;
             color: white;
             text-decoration: none;
-            padding: 10px 20px;
+            padding: 12px 25px;
             border-radius: 5px;
-            margin: 20px 0;
+            font-weight: 500;
+        }
+        .getting-started {
+            margin-top: 20px;
+            padding: 15px;
+            background-color: #e8f5e9;
+            border-radius: 5px;
+            border-left: 4px solid #2D7738;
         }
         .footer {
-            margin-top: 20px;
+            padding: 20px;
-            font-size: 12px;
             text-align: center;
+            font-size: 12px;
             color: #777;
+            border-top: 1px solid #eaeaea;
         }
     </style>
 </head>
 <body>
-    <div class="header">
+    <div class="container">
-        <h1>Welcome to LeagueLedger!</h1>
+        <div class="header">
-    </div>
+            <h1>Welcome to LeagueLedger!</h1>
-    
+        </div>
-    <div class="content">
-        <p>Hello {{ username }},</p>
         
-        <p>Welcome to LeagueLedger! We're excited to have you join our community.</p>
+        <div class="content">
+            <p>Hello {{ username }},</p>
+            
+            <p>Thank you for joining LeagueLedger! We're delighted to have you as part of our community of pub quiz enthusiasts.</p>
+            
+            <div class="feature-list">
+                <h3>With your new account, you can:</h3>
+                <ul>
+                    <li><strong>Join or create teams</strong> - Connect with friends and form your pub quiz dream team</li>
+                    <li><strong>Track your progress</strong> - Keep a record of all your quiz results in one place</li>
+                    <li><strong>Earn achievements</strong> - Get recognition for your team's accomplishments</li>
+                    <li><strong>Compete on leaderboards</strong> - See how your team ranks against others</li>
+                    <li><strong>Scan QR codes</strong> - Easily record your points after quiz nights</li>
+                </ul>
+            </div>
+            
+            <div class="getting-started">
+                <h3>Getting Started</h3>
+                <p>The best way to begin is to either join an existing team or create your own. Visit your dashboard to get started!</p>
+            </div>
+            
+            <div class="button-container">
+                <a href="{{ base_url }}/dashboard" class="button">Go to My Dashboard</a>
+            </div>
+            
+            <p>If you have any questions or need assistance, you can reply to this email or visit our help center.</p>
+            
+            <p>We're excited to see you and your team climb the leaderboards!</p>
+            
+            <p>Best regards,<br>The LeagueLedger Team</p>
+        </div>
         
-        <p>With LeagueLedger, you can:</p>
+        <div class="footer">
-        <ul>
+            <p>© 2025 LeagueLedger. All rights reserved.</p>
-            <li>Track your team's progress</li>
+            <p>This email was sent to welcome you to the LeagueLedger platform.</p>
-            <li>Participate in events</li>
+        </div>
-            <li>Collect points and earn achievements</li>
-            <li>Connect with other teams and players</li>
-        </ul>
-        
-        <p>If you have any questions or need assistance, feel free to reach out to our support team.</p>
-        
-        <p style="text-align: center;">
-            <a href="{{ base_url }}/dashboard" class="button">Go to Dashboard</a>
-        </p>
-        
-        <p>Best regards,<br>The LeagueLedger Team</p>
-    </div>
-    
-    <div class="footer">
-        <p>© LeagueLedger. All rights reserved.</p>
-        <p>This is an automated message, please do not reply to this email.</p>
     </div>
 </body>
 </html>

app/utils/mail.py

@@ -1,15 +1,21 @@
 """
-Email utility module for LeagueLedger using FastAPI-Mail
+Email utility module for LeagueLedger using Python's built-in email and smtplib packages
 """
 import os
+import smtplib
+import asyncio
+from email.mime.multipart import MIMEMultipart
+from email.mime.text import MIMEText
+from email.utils import formatdate
 from pathlib import Path
-from typing import List, Dict, Any, Optional
+from typing import List, Dict, Any, Optional, Union
 from fastapi import BackgroundTasks
-from fastapi_mail import FastMail, MessageSchema, ConnectionConfig, MessageType
 from pydantic import EmailStr
 from dotenv import load_dotenv
 from jinja2 import Environment, FileSystemLoader
 import logging
+import re
+from bs4 import BeautifulSoup
 
 # Setup logging
 logger = logging.getLogger(__name__)
@@ -26,51 +32,130 @@ MAIL_PORT = int(os.getenv("MAIL_PORT", "587"))
 MAIL_FROM_NAME = os.getenv("MAIL_FROM_NAME", "LeagueLedger")
 MAIL_STARTTLS = os.getenv("MAIL_STARTTLS", "True").lower() == "true"
 MAIL_SSL_TLS = os.getenv("MAIL_SSL_TLS", "False").lower() == "true"
-USE_CREDENTIALS = os.getenv("MAIL_USE_CREDENTIALS", "True").lower() == "true"
-VALIDATE_CERTS = os.getenv("MAIL_VALIDATE_CERTS", "True").lower() == "true"
 APP_BASE_URL = os.getenv("LEAGUELEDGER_BASE_URL", os.getenv("APP_BASE_URL", "http://localhost:8000"))
 
 # Configure Jinja2 for email templates
 template_dir = os.path.join(os.path.dirname(os.path.dirname(__file__)), "templates")
 env = Environment(loader=FileSystemLoader(template_dir))
 
-# Configure email connection
+def html_to_plain_text(html_content):
-conf = ConnectionConfig(
+    """
-    MAIL_USERNAME=MAIL_USERNAME,
+    Convert HTML content to plain text for email alternatives.
-    MAIL_PASSWORD=MAIL_PASSWORD,
+    This helps improve email deliverability by providing a plain text version.
-    MAIL_FROM=MAIL_FROM,
+    """
-    MAIL_PORT=MAIL_PORT,
+    if not html_content:
-    MAIL_SERVER=MAIL_SERVER,
+        return ""
-    MAIL_FROM_NAME=MAIL_FROM_NAME,
+    
-    MAIL_STARTTLS=MAIL_STARTTLS,
+    # Use BeautifulSoup to parse HTML
-    MAIL_SSL_TLS=MAIL_SSL_TLS,
+    try:
-    USE_CREDENTIALS=USE_CREDENTIALS,
+        soup = BeautifulSoup(html_content, 'html.parser')
-    VALIDATE_CERTS=VALIDATE_CERTS
+        
-)
+        # Get text from HTML
+        text = soup.get_text(separator='\n', strip=True)
+        
+        # Clean up extra whitespace and handle links
+        text = re.sub(r'\n\s+\n', '\n\n', text)
+        text = re.sub(r'\n{3,}', '\n\n', text)
+        
+        return text
+    except Exception as e:
+        logger.error(f"Error converting HTML to plain text: {str(e)}")
+        # Fallback: Basic HTML tag removal
+        plain = re.sub('<.*?>', '', html_content)
+        return plain.replace('&nbsp;', ' ').strip()
 
-async def send_email(
+async def _send_email_async(
-    email_to: List[EmailStr],
+    email_to: Union[str, List[str]],
     subject: str,
     html_content: str,
-    background_tasks: BackgroundTasks
+    plain_text_content: Optional[str] = None
-):
+) -> bool:
+    """
+    Asynchronous function to send emails using Python's built-in email and smtplib packages.
+    This function handles the actual sending of the email.
+    """
+    # Convert single email to list if needed
+    recipients = [email_to] if isinstance(email_to, str) else email_to
+    
+    # Generate plain text from HTML if not provided
+    if plain_text_content is None:
+        plain_text_content = html_to_plain_text(html_content)
+    
+    try:
+        # Create multipart message container
+        msg = MIMEMultipart('alternative')
+        msg['Subject'] = subject
+        msg['From'] = f"{MAIL_FROM_NAME} <{MAIL_FROM}>"
+        msg['To'] = ", ".join(recipients)
+        msg['Date'] = formatdate(localtime=True)
+        
+        # Attach plain text part first (will be displayed if HTML not supported)
+        # RFC 2046 defines that the last part is preferred
+        part1 = MIMEText(plain_text_content, 'plain', 'utf-8')
+        msg.attach(part1)
+        
+        # Attach HTML part last (will be preferred by most email clients)
+        part2 = MIMEText(html_content, 'html', 'utf-8')
+        msg.attach(part2)
+        
+        # Run SMTP connection in a separate thread to avoid blocking
+        result = await asyncio.to_thread(_send_smtp_email, msg, recipients)
+        return result
+    except Exception as e:
+        logger.error(f"Failed to send email: {str(e)}")
+        return False
+
+def _send_smtp_email(msg, recipients):
+    """
+    Helper function to handle SMTP connection and sending.
+    This runs in a separate thread to avoid blocking the main event loop.
+    """
+    try:
+        # Choose the appropriate SMTP connection method
+        if MAIL_SSL_TLS:
+            server = smtplib.SMTP_SSL(MAIL_SERVER, MAIL_PORT)
+        else:
+            server = smtplib.SMTP(MAIL_SERVER, MAIL_PORT)
+            
+            # Use STARTTLS if configured
+            if MAIL_STARTTLS:
+                server.starttls()
+        
+        # Login if credentials provided
+        if MAIL_USERNAME and MAIL_PASSWORD:
+            server.login(MAIL_USERNAME, MAIL_PASSWORD)
+        
+        # Send email
+        server.send_message(msg)
+        server.quit()
+        
+        logger.info(f"Email sent successfully to {recipients}")
+        return True
+    except Exception as e:
+        logger.error(f"SMTP error: {str(e)}")
+        return False
+
+async def send_email(
+    email_to: Union[str, List[str]],
+    subject: str,
+    html_content: str,
+    background_tasks: BackgroundTasks,
+    plain_text_content: Optional[str] = None
+) -> bool:
     """Generic function to send emails"""
     try:
-        message = MessageSchema(
+        # Add email sending to background tasks
+        background_tasks.add_task(
+            _send_email_async,
+            email_to=email_to,
             subject=subject,
-            recipients=[email_to] if isinstance(email_to, str) else email_to,
+            html_content=html_content,
-            body=html_content,
+            plain_text_content=plain_text_content
-            subtype="html"
         )
-        
-        fm = FastMail(conf)
-        
-        # Send email in the background to avoid blocking the main thread
-        background_tasks.add_task(fm.send_message, message)
         logger.info(f"Email queued for sending to {email_to}")
         return True
     except Exception as e:
-        logger.error(f"Failed to send email: {str(e)}")
+        logger.error(f"Failed to queue email: {str(e)}")
         return False
 
 async def send_password_reset_email(
@@ -178,12 +263,37 @@ async def send_verification_email(
             verification_link=verification_link
         )
         
-        # Send email
+        # Generate plain text version explicitly
+        plain_text = f"""
+Hello {username},
+
+Thank you for creating an account with LeagueLedger, your pub quiz team tracking platform. We're excited to have you join our community!
+
+To ensure account security and complete your registration, please verify your email address by visiting this link:
+{verification_link}
+
+This verification step helps us keep your account secure and allows you to:
+- Create or join teams
+- Track your quiz night scores
+- Earn points and achievements
+- Climb the leaderboards
+
+If you did not create an account with LeagueLedger, please disregard this email.
+
+Best regards,
+The LeagueLedger Team
+
+© 2025 LeagueLedger. All rights reserved.
+This email was sent to verify your account registration.
+"""
+        
+        # Send email with both HTML and plain text versions
         subject = "Verify Your Email Address - LeagueLedger"
         await send_email(
             email_to=recipient_email,
             subject=subject,
             html_content=html_content,
+            plain_text_content=plain_text,
             background_tasks=background_tasks
         )
         logger.info(f"Verification email sent to {recipient_email}")
@@ -226,3 +336,37 @@ async def send_join_request_response(
     except Exception as e:
         logger.error(f"Failed to send join request response email: {str(e)}")
         return False
+
+async def send_welcome_email(
+    email_to: str,
+    username: str,
+    background_tasks: BackgroundTasks
+):
+    """Send welcome email to newly registered users after verification"""
+    try:
+        # Get the email template
+        template = env.get_template("email/welcome.html")
+        
+        # Render the HTML content with variables
+        html_content = template.render(
+            username=username,
+            base_url=APP_BASE_URL
+        )
+        
+        # Generate plain text version
+        plain_text_content = html_to_plain_text(html_content)
+        
+        # Send email
+        subject = "Welcome to LeagueLedger!"
+        await send_email(
+            email_to=email_to,
+            subject=subject,
+            html_content=html_content,
+            plain_text_content=plain_text_content,
+            background_tasks=background_tasks
+        )
+        logger.info(f"Welcome email sent to {email_to}")
+        return True
+    except Exception as e:
+        logger.error(f"Failed to send welcome email: {str(e)}")
+        return False

app/views/auth.py

@@ -220,6 +220,7 @@ async def register_post(
 @router.get("/verify-email", response_class=HTMLResponse)
 async def verify_email(
     request: Request,
+    background_tasks: BackgroundTasks,
     token: str,
     db: Session = Depends(get_db)
 ):
@@ -243,11 +244,10 @@ async def verify_email(
     # Send welcome email in the background
     try:
         from ..utils.mail import send_welcome_email
-        background_tasks = BackgroundTasks()
+        await send_welcome_email(
-        background_tasks.add_task(
+            email_to=user.email,
-            send_welcome_email,
+            username=user.username,
-            email=user.email,
+            background_tasks=background_tasks
-            username=user.username
         )
     except Exception as e:
         print(f"Failed to queue welcome email: {str(e)}")
@@ -818,7 +818,7 @@ async def forgot_password_post(
         try:
             # Send reset email
             await send_password_reset_email(
-                email=user.email,
+                email_to=user.email,
                 username=user.username,
                 reset_token=reset_token,
                 background_tasks=background_tasks,

app/views/teams.py

@@ -13,7 +13,7 @@ from starlette.status import HTTP_303_SEE_OTHER
 from starlette.middleware.sessions import SessionMiddleware
 
 from ..db import SessionLocal, get_db
-from ..models import Team, TeamMembership, User, QRCode, TeamAchievement, TeamMember, TeamJoinRequest
+from ..models import Team, TeamMembership, User, QRCode, TeamAchievement, TeamJoinRequest
 from ..schemas import TeamCreate
 from ..templates_config import templates
 from ..utils.auth import get_current_user, is_team_captain
@@ -90,28 +90,21 @@ async def create_team_post(
         name=name,
         description=description,
         logo_url=logo_url,
-        is_open=is_open  # Save is_open value
+        is_open=is_open,  # Save is_open value
+        owner_id=current_user.id  # Set the owner_id field
     )
     db.add(team)
     db.commit()
     db.refresh(team)
     
-    # Make the user an admin of the team in TeamMembership
+    # Make the user an admin and captain of the team in TeamMembership
     team_membership = TeamMembership(
         user_id=current_user.id,
         team_id=team.id,
-        is_admin=True  # User becomes admin of the team
+        is_admin=True,
+        is_captain=True  # User becomes both admin and captain of the team
     )
     db.add(team_membership)
-    
-    # Create TeamMember relationship as well
-    team_member = TeamMember(
-        user_id=current_user.id,
-        team_id=team.id,
-        is_captain=True  # Use is_captain instead of role
-    )
-    db.add(team_member)
-    
     db.commit()
 
     return RedirectResponse("/teams/", status_code=HTTP_303_SEE_OTHER)
@@ -173,9 +166,9 @@ async def join_team_page(
         )
     
     # Check if user is already a member
-    existing_membership = db.query(TeamMember).filter(
+    existing_membership = db.query(TeamMembership).filter(
-        TeamMember.team_id == team_id, 
+        TeamMembership.team_id == team_id, 
-        TeamMember.user_id == current_user.id
+        TeamMembership.user_id == current_user.id
     ).first()
     
     if existing_membership:
@@ -232,9 +225,9 @@ async def join_team_request(
         )
     
     # Check if user is already a member
-    existing_membership = db.query(TeamMember).filter(
+    existing_membership = db.query(TeamMembership).filter(
-        TeamMember.team_id == team_id, 
+        TeamMembership.team_id == team_id, 
-        TeamMember.user_id == current_user.id
+        TeamMembership.user_id == current_user.id
     ).first()
     
     if existing_membership:
@@ -243,10 +236,11 @@ async def join_team_request(
     # Open team - directly add the user
     if team.is_open:
         # Add user to team
-        new_member = TeamMember(
+        new_member = TeamMembership(
             team_id=team_id,
             user_id=current_user.id,
-            is_captain=False  # Use is_captain instead of role
+            is_captain=False,
+            is_admin=False
         )
         
         db.add(new_member)
@@ -286,9 +280,9 @@ async def join_team_request(
     db.commit()
     
     # Get team captains to notify
-    captains = db.query(User).join(TeamMember).filter(
+    captains = db.query(User).join(TeamMembership).filter(
-        TeamMember.team_id == team_id,
+        TeamMembership.team_id == team_id,
-        TeamMember.is_captain == True  # Use is_captain instead of role
+        TeamMembership.is_captain == True
     ).all()
     
     if not captains:
@@ -352,17 +346,10 @@ def direct_join_team(request: Request, team_id: int, db: Session = Depends(get_d
     new_member = TeamMembership(
         user_id=user_id,
         team_id=team.id,
-        is_admin=False
+        is_admin=False,
+        is_captain=False
     )
     db.add(new_member)
-    
-    # Also create TeamMember record for consistency
-    team_member = TeamMember(
-        user_id=user_id,
-        team_id=team.id,
-        is_captain=False  # Use is_captain instead of role
-    )
-    db.add(team_member)
     db.commit()
     
     # Redirect to the team detail page

docker-compose.yml

@@ -110,7 +110,7 @@ services:
     container_name: pubquiz_mailpit
     restart: unless-stopped
     ports:
-      - "8025:8025"  # Web UI
+      - "8025:8025"  # Web UI - Access emails at http://localhost:8025/
       - "1025:1025"  # SMTP Server
     environment:
       MH_STORAGE: "memory"  # Store emails in memory (they will be lost on container restart)

requirements.txt

@@ -34,7 +34,7 @@ psutil>=5.9.0  # System monitoring and statistics
 python-dateutil>=2.8.2  # Date manipulation utilities
 
 # Email support
-fastapi-mail>=1.4.2
+beautifulsoup4>=4.12.2  # HTML parsing for emails
 
 # Image processing library for QR code generation
 Pillow>=9.0.0