diff --git a/.gitignore b/.gitignore
index a97b897..6332952 100644
--- a/.gitignore
+++ b/.gitignore
@@ -1,6 +1,6 @@
 .env
 
-instance/
+.instance/
 *.db
 
 documents/
@@ -12,6 +12,10 @@ __pycache__/
 
 .pytest_cache/
 .coverage
+
 htmlcov/
 .DS_Store
-*.log
\ No newline at end of file
+*.log
+
+.certs/
+*.pem
\ No newline at end of file
diff --git a/instance/team_tryouts.db b/instance/team_tryouts.db
index b8d9f0f..b1569f0 100644
Binary files a/instance/team_tryouts.db and b/instance/team_tryouts.db differ
diff --git a/run_https.py b/run_https.py
new file mode 100644
index 0000000..65af865
--- /dev/null
+++ b/run_https.py
@@ -0,0 +1,129 @@
+"""Development HTTPS server for testing production settings locally.
+
+Generates a self-signed certificate (if not present) and runs the
+application via Waitress wrapped in a TLS socket. This simulates the
+production environment where Nginx handles TLS termination.
+
+Usage:
+    python run_https.py
+
+The server will listen on https://localhost:8443
+Accept the self-signed certificate warning in your browser to proceed.
+"""
+
+import os
+import socket
+import subprocess
+import ssl
+import sys
+from waitress.server import create_server
+from app import create_app
+
+CERT_FILE = 'certs/localhost.pem'
+KEY_FILE = 'certs/localhost-key.pem'
+
+
+def generate_self_signed_cert():
+    """Generate a self-signed certificate for local HTTPS testing.
+
+    Uses OpenSSL to create a key and certificate valid for 365 days.
+    Skips generation if certificate files already exist.
+    """
+    if os.path.exists(CERT_FILE) and os.path.exists(KEY_FILE):
+        print('[OK] Self-signed certificate already exists.')
+        return
+
+    os.makedirs('certs', exist_ok=True)
+
+    print('[INFO] Generating self-signed certificate for localhost...')
+    try:
+        subprocess.run([
+            'openssl', 'req', '-x509', '-newkey', 'rsa:2048',
+            '-keyout', KEY_FILE,
+            '-out', CERT_FILE,
+            '-days', '365',
+            '-nodes',
+            '-subj', '/CN=localhost'
+        ], check=True, capture_output=True)
+        print('[OK] Certificate generated: certs/localhost.pem')
+    except FileNotFoundError:
+        print('[ERROR] OpenSSL not found. Install OpenSSL or use:')
+        print('  winget install OpenSSL.OpenSSL')
+        print('  OR download from https://slproweb.com/products/Win32OpenSSL.html')
+        sys.exit(1)
+    except subprocess.CalledProcessError as e:
+        print(f'[ERROR] Certificate generation failed: {e}')
+        sys.exit(1)
+
+
+def main():
+    """Start the HTTPS development server."""
+    port = int(os.getenv('HTTPS_PORT', 8443))
+    host = os.getenv('HOST', '127.0.0.1')
+
+    # Ensure certificate exists
+    generate_self_signed_cert()
+
+    # Create the Flask application
+    app = create_app()
+
+    # Create SSL context
+    context = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER)
+    context.load_cert_chain(CERT_FILE, KEY_FILE)
+
+    # Create a TCP socket, wrap it with TLS, then pass to Waitress
+    sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM, 0)
+    sock.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+    sock.bind((host, port))
+    sock.listen(5)
+
+    # Wrap the socket with TLS
+    ssl_sock = context.wrap_socket(sock, server_side=True)
+
+    # =====================================================================
+    # WSGI Middleware: Tell Flask the connection is HTTPS
+    #
+    # Waitress doesn't know the underlying socket is TLS, so Flask sees
+    # wsgi.url_scheme = "http". Without this middleware, force_https()
+    # would cause an infinite redirect loop (ERR_TOO_MANY_REDIRECTS).
+    # =====================================================================
+    class ForceHTTPSMiddleware:
+        """WSGI middleware that sets url_scheme to 'https'.
+
+        Since we're wrapping the TCP socket with SSL before passing it
+        to Waitress, Flask's request.is_secure returns False because
+        Waitress reports wsgi.url_scheme='http'. This middleware fixes
+        that so Flask correctly identifies the connection as HTTPS.
+        """
+
+        def __init__(self, wsgi_app):
+            self.wsgi_app = wsgi_app
+
+        def __call__(self, environ, start_response):
+            environ['wsgi.url_scheme'] = 'https'
+            environ['HTTPS'] = 'on'
+            return self.wsgi_app(environ, start_response)
+
+    # Wrap the Flask app with the HTTPS middleware
+    app.wsgi_app = ForceHTTPSMiddleware(app.wsgi_app)
+
+    print(f'\n╔══════════════════════════════════════════════════════╗')
+    print(f'║  TEAM TRYOUTS - Development HTTPS Server            ║')
+    print(f'╠══════════════════════════════════════════════════════╣')
+    print(f'║  URL: https://{host}:{port}                      ║')
+    print(f'║  Cert: self-signed (accept browser warning)         ║')
+    print(f'║  Press Ctrl+C to stop                               ║')
+    print(f'╚══════════════════════════════════════════════════════╝\n')
+
+    # Create Waitress server with the SSL-wrapped socket
+    server = create_server(
+        app,
+        sockets=[ssl_sock],
+        threads=4,
+        channel_timeout=30,
+    )
+    server.run()
+
+
+if __name__ == '__main__':
+    main()