diff --git a/src/test_webhook.py b/src/test_webhook.py
index 491a27f..c677829 100644
--- a/src/test_webhook.py
+++ b/src/test_webhook.py
@@ -6,9 +6,11 @@ Sends the Square inventory.count.updated webhook payload
 import asyncio
 import aiohttp
 import json
+import ssl
+import sys
 
 
-async def test_webhook():
+async def test_webhook(verify_ssl=True):
     url = "https://studspider.sh:8443/hook"
 
     # Your Square webhook payload
@@ -36,11 +38,23 @@ async def test_webhook():
     }
 
     print("Sending webhook test payload...")
+    print(f"URL: {url}")
+    print(
+        f"SSL Verification: {'Enabled' if verify_ssl else 'Disabled (accepting self-signed certs)'}"
+    )
     print(json.dumps(payload, indent=2))
     print("\n" + "=" * 60 + "\n")
 
+    # Create SSL context that allows self-signed certificates if verify_ssl is False
+    ssl_context = None
+    if not verify_ssl:
+        ssl_context = ssl.create_default_context()
+        ssl_context.check_hostname = False
+        ssl_context.verify_mode = ssl.CERT_NONE
+
     try:
-        async with aiohttp.ClientSession() as session:
+        connector = aiohttp.TCPConnector(ssl=ssl_context)
+        async with aiohttp.ClientSession(connector=connector) as session:
             async with session.post(url, json=payload) as resp:
                 print(f"Status: {resp.status}")
                 print(f"Response headers: {dict(resp.headers)}")
@@ -56,10 +70,33 @@ async def test_webhook():
 
     except aiohttp.ClientConnectorError as e:
         print(f"Connection error: {e}")
-        print("Make sure the server is running with: python src/test_server.py")
+        print("\nTroubleshooting:")
+        print("1. Make sure the server is running")
+        print("2. Check if the hostname and port are correct")
+        print("3. For self-signed certificates, the script now accepts them by default")
+        print("\nServer start command:")
+        print(
+            "  python src/test_server.py --ssl-cert cert.pem --ssl-key key.pem --hook-port 8443 --hook-ssl-only"
+        )
+    except aiohttp.ServerTimeoutError as e:
+        print(f"Timeout error: {e}")
+        print("The server took too long to respond")
     except Exception as e:
-        print(f"Error: {e}")
+        print(f"Error: {type(e).__name__}: {e}")
 
 
 if __name__ == "__main__":
-    asyncio.run(test_webhook())
+    # Check command line arguments
+    verify_ssl = True
+    if len(sys.argv) > 1 and sys.argv[1] in ["--no-verify", "--insecure", "-k"]:
+        verify_ssl = False
+        print("⚠️  SSL verification disabled - accepting self-signed certificates\n")
+    elif len(sys.argv) > 1:
+        print("Usage: python src/test_webhook.py [--no-verify]")
+        print(
+            "  --no-verify: Disable SSL certificate verification (for self-signed certs)"
+        )
+        sys.exit(1)
+
+    # Default to no verification since we're likely using self-signed certs
+    asyncio.run(test_webhook(verify_ssl=False))