added automatic waitlist email sending

app/__init__.py

@@ -2,6 +2,7 @@ from flask import Flask
 from app.config import Config
 from app.extensions import db, mail, limiter
 from werkzeug.middleware.proxy_fix import ProxyFix
+import logging
 
 def create_app(config_class=Config):
     app = Flask(__name__)
@@ -9,6 +10,10 @@ def create_app(config_class=Config):
 
     app.wsgi_app = ProxyFix(app.wsgi_app, x_for=1, x_proto=1)
 
+    gunicorn_logger = logging.getLogger("gunicorn.error")
+    app.logger.handlers = gunicorn_logger.handlers
+    app.logger.setLevel(gunicorn_logger.level)
+
     # Initialize extensions
     db.init_app(app)
     mail.init_app(app)

app/routes.py

@@ -30,6 +30,7 @@ def send_verification_email(user, is_new=True):
         msg = Message('Verify your CTF Registration', recipients=[user.email])
         msg.html = render_template("email.html", user_name=user.name, register_link=register_link, remove_link=remove_link, logo_url=logo)
         mail.send(msg)
+        current_app.logger.info(f"Sent verification email to {user.email}")
         user.num_emails_sent += 1
         db.session.commit()
         if is_new:
@@ -43,8 +44,24 @@ def send_waitlist_email(user):
     msg = Message('h4tum CTF 2026 Registration', recipients=[user.email])
     logo = url_for('static', filename='h4tum_white.png', _external=True)
     msg.html = render_template("waitlist_email.html", logo_url=logo, user_name=user.name)
+    current_app.logger.info(msg)
     mail.send(msg)
 
+def send_waitlist_newsletter():
+    results = db.session.query(Participant.email).filter(Participant.on_waitlist == True).all()
+    waitlist_emails = [r[0] for r in results]
+    logo = url_for('static', filename='h4tum_white.png', _external=True)
+    s = URLSafeTimedSerializer(current_app.config['SECRET_KEY'])
+    for email in waitlist_emails:
+        register_token = s.dumps(email, salt='email-confirm-h4tum-ctf-2025')
+        register_link = url_for('main.verify_email', token=register_token, _external=True)
+        remove_token = s.dumps(email, salt='email-remove-h4tum-ctf-2026')
+        remove_link = url_for('main.remove_registration', token=remove_token, _external=True)
+        msg = Message('h4tum CTF 2026 Free Spot available', recipients=[email])
+        msg.html = render_template("waitlist_maillist_email.html", logo_url=logo, register_link=register_link, remove_link=remove_link)
+        mail.send(msg)
+        current_app.logger.info(f"Sent waitlist newsletter email to {email}")
+
 @bp.route('/', methods=['GET', 'POST'])
 @limiter.limit("5 per hour", methods=["POST"])
 def index():
@@ -109,9 +126,11 @@ def verify_email(token):
         if user.confirmed:
             return render_template('success.html', message="You are confirmed", discord_link=current_app.config['DISCORD_LINK'], discord_token=user.discord_token)
         else:
-            return render_template("error.html", error_message="Sorry! The event filled up while you were verifying.")
+            return render_template("error.html", error_message="Sorry! The event filled up while you were claiming the last spot.")
     else:
         user.confirmed = True
+        if user.on_waitlist:
+            user.on_waitlist = False
         db.session.commit()
 
         discord_link = current_app.config['DISCORD_LINK']
@@ -137,16 +156,14 @@ def remove_registration(token):
 
     if not user:
         return render_template("error.html", error_message="No user found.")
-    
-    try:
-        db.session.delete(user)
-        db.session.commit()
-        return render_template("deregistered.html", message="Sad to see you go. Comeback next time :D")
-    except:
-        db.session.rollback()
-        return render_template("error.html", error_message="Removing user did not work")
+    db.session.delete(user)
+    db.session.commit()
+
+    if get_confirmed_count() == current_app.config['MAX_SPOTS'] - 1:
+        send_waitlist_newsletter()
+
+    return render_template("deregistered.html", message="Sad to see you go. Comeback next time :D")
 
-    
 @bp.route('/dsgvo')
 @limiter.exempt
 def dsgvo():

app/templates/waitlist_maillist_email.html

@@ -0,0 +1,69 @@
+<html>
+<body style="margin: 0; padding: 0; background-color: #1a1a1a; font-family: 'Courier New', Courier, monospace; color: #ffffff;">
+    <table width="100%" border="0" cellspacing="0" cellpadding="0" style="background-color: #1a1a1a; padding: 20px;">
+        <tr>
+            <td align="center">
+                <table width="100%" border="0" cellspacing="0" cellpadding="0" style="max-width: 600px; background-color: #222222; border: 1px solid #00ff00; padding: 30px;">
+                    
+                    <tr>
+                        <td align="center" style="padding-bottom: 20px;">
+                          <img src="{{ logo_url }}" alt="Club Logo" width="150" style="display: block; border: 0;">
+                        </td>
+                    </tr>
+
+                    <tr>
+                        <td align="center" style="padding-bottom: 20px;">
+                            <h1 style="color: #00ff00; font-size: 24px; margin: 0; text-transform: uppercase; text-align: center;">Registration Received</h1>
+                        </td>
+                    </tr>
+
+                    <tr>
+                        <td align="center" style="padding-bottom: 30px; font-size: 16px; line-height: 1.5; text-align: center;">
+                            A spot has just become available for h4tum CTF 2026! Be fast and claim it!
+                        </td>
+                    </tr>
+
+                    <tr>
+                        <td align="center" style="padding-bottom: 30px;">
+                            <table border="0" cellspacing="0" cellpadding="0" align="center">
+                                <tr>
+                                    <td align="center" bgcolor="#00ff00" style="padding: 15px 25px;">
+                                        <a href="{{ register_link }}" target="_blank" style="font-size: 18px; font-weight: bold; color: #000000; text-decoration: none; display: inline-block;">
+                                            CLAIM THE SPOT
+                                        </a>
+                                    </td>
+                                </tr>
+                            </table>
+                        </td>
+                    </tr>
+
+                    <tr>
+                        <td align="center" style="padding-bottom: 30px; font-size: 16px; line-height: 1.5; text-align: center;">
+                            If you can not attend anymore / don't want to receive any further emails:
+                        </td>
+                    </tr>
+                    <tr>
+                        <td align="center" style="padding-bottom: 30px;">
+                            <table border="0" cellspacing="0" cellpadding="0" align="center">
+                                <tr>
+                                    <td align="center" bgcolor="#D32F2F" style="padding: 15px 25px;">
+                                        <a href="{{ remove_link }}" target="_blank" style="font-size: 18px; font-weight: bold; color: #000000; text-decoration: none; display: inline-block;">
+                                           DEREGISTER
+                                        </a>
+                                    </td>
+                                </tr>
+                            </table>
+                        </td>
+                    </tr>
+                    <tr>
+                        <td align="center" style="padding-top: 20px; border-top: 1px solid #333333; font-size: 12px; color: #888888; text-align: center;">
+                            This email is sent automatically every time a place becomes available. You can unsubscribe by pressing the big red button.
+                        </td>
+                    </tr>
+
+                </table>
+            </td>
+        </tr>
+    </table>
+</body>
+</html>