ssl-proxy-debug-workflow

SSL/Proxy Debugging Workflow for Government Websites

This skill provides a systematic approach to troubleshoot and resolve SSL certificate, proxy, and connectivity issues commonly encountered when accessing government and institutional websites.

Recognizing the Problem

Typical symptoms indicating SSL/proxy issues:

• requests.exceptions.SSLError or certificate verify failed errors
• Connection timeouts despite the site being publicly accessible
• Proxy authentication failures
• HTTP 403/407 errors on otherwise valid requests
• Mixed success across different access methods (browser works, script fails)

Systematic Troubleshooting Steps

Step 1: Verify Basic Connectivity

Before assuming SSL issues, confirm the target is reachable:

import requests
import socket

# Test DNS resolution
try:
    ip = socket.gethostbyname('example.gov')
    print(f"DNS resolved: {ip}")
except Exception as e:
    print(f"DNS failure: {e}")

# Test basic TCP connectivity
try:
    sock = socket.create_connection(('example.gov', 443), timeout=5)
    sock.close()
    print("TCP connection successful")
except Exception as e:
    print(f"TCP failure: {e}")

Step 2: Try Protocol Variations

Test both HTTP and HTTPS, and try without www prefix:

urls_to_try = [
    'https://example.gov',
    'http://example.gov',
    'https://www.example.gov',
    'http://www.example.gov',
    'https://subdomain.example.gov',
]

for url in urls_to_try:
    try:
        response = requests.get(url, timeout=10)
        print(f"SUCCESS: {url} - Status: {response.status_code}")
        break
    except Exception as e:
        print(f"FAILED: {url} - {type(e).__name__}: {e}")

Step 3: Disable SSL Verification (Temporary Debug)

For debugging only - never use in production with sensitive data:

import urllib3
urllib3.disable_warnings(urllib3.exceptions.InsecureRequestWarning)

response = requests.get('https://example.gov', verify=False, timeout=10)
print(f"Status: {response.status_code}")