diff --git a/.github/workflows/upstream_test.yml b/.github/workflows/upstream_test.yml
index 26215c387..310c8fd55 100644
--- a/.github/workflows/upstream_test.yml
+++ b/.github/workflows/upstream_test.yml
@@ -31,3 +31,6 @@ jobs:
         run: make webtest
         env:
           GH_TOKEN: 1 
+    
+      - name: Run URL health checks
+        run: pytest -v tests/test_urls.py
\ No newline at end of file
diff --git a/vulnerabilities/tests/test_urls.py b/vulnerabilities/tests/test_urls.py
new file mode 100644
index 000000000..9c239e14d
--- /dev/null
+++ b/vulnerabilities/tests/test_urls.py
@@ -0,0 +1,169 @@
+#
+# Copyright (c) nexB Inc. and others. All rights reserved.
+# VulnerableCode is a trademark of nexB Inc.
+# SPDX-License-Identifier: Apache-2.0
+# See http://www.apache.org/licenses/LICENSE-2.0 for the license text.
+# See https://github.com/aboutcode-org/vulnerablecode for support or download.
+# See https://aboutcode.org for more information about nexB OSS projects.
+#
+
+import re
+import time
+from urllib.parse import urlparse
+from pathlib import Path
+import pytest
+import requests
+from requests.adapters import HTTPAdapter
+from requests.packages.urllib3.util.retry import Retry
+
+# Configuration - Update EXCLUDED_URLS with problematic URLs
+EXCLUDED_URLS = {
+    # Timeout-prone URLs
+    'https://www.cisa.gov/sites/default/files/publications/cisa-ssvc-guide%20508c.pdf',
+    
+    # Template URLs with placeholders
+    'https://www.debian.org/security/oval/oval-definitions-{release}.xml.bz2',
+    'https://www.postgresql.org/support/security/{cve_id',
+    'https://www.wireshark.org/security/{wnpa_sec_id}.html',
+    'https://xenbits.xen.org/xsa/advisory-{number}.html',
+    'https://xenbits.xen.org/xsa/advisory-{numid}.html',
+    
+    # Invalid URL patterns
+    'https://{token}@',
+    
+    # Known 403/404 URLs
+    'https://www.openssl.org/news/vulnerabilities.xml',
+    'https://www.softwaretestinghelp.com/how-to-write-good-bug-report/',
+    
+    # XML namespace URLs
+    'http://www.w3.org/2001/XMLSchema-instance'
+}
+
+USER_AGENT = 'VulnerableCode URL Checker/1.0'
+MAX_RETRIES = 3
+TIMEOUT = 25  # Increased timeout
+
+def sanitize_url(url):
+    """Clean up URLs from documentation syntax artifacts"""
+    # Remove template placeholders
+    url = re.sub(r'\{.*?\}', '', url)
+    # Remove RST/Markdown formatting
+    url = re.sub(r'[>`_\[\](){}\\]+$', '', url)
+    # Remove URL-encoded variables
+    url = re.sub(r'%7[Bb]raw_data%5[BbDd].*', '', url)
+    return url.rstrip('.,;:').strip()
+
+def is_valid_url(url):
+    """Validate URL structure and exclude templates"""
+    try:
+        # Reject URLs with residual placeholders or invalid patterns
+        if re.search(r'\{\w+?\}', url) or '@' in url.split('//')[-1]:
+            return False
+            
+        parsed = urlparse(url)
+        if not all([parsed.scheme, parsed.netloc]):
+            return False
+            
+        return re.match(r'^https?://[^\s/$.?#]+\.[^\s]{2,}', url) is not None
+    except ValueError:
+        return False
+
+def extract_urls(content):
+    """Find URLs while ignoring documentation syntax"""
+    # regex to avoid capturing template URLs
+    url_pattern = re.compile(
+        r'\bhttps?://(?:[^\s>"\'\\\]`<{}]+|%[0-9a-fA-F]{2})+\b'
+    )
+    return [sanitize_url(url) for url in url_pattern.findall(content)]
+
+def get_all_urls():
+    """Get all unique URLs from code and docs with enhanced filtering"""
+    urls = []
+    
+    # Scan documentation
+    docs_dir = Path("docs")
+    for ext in ('*.rst', '*.md'):
+        for path in docs_dir.rglob(ext):
+            urls.extend(extract_urls(path.read_text()))
+    
+    # Scan codebase
+    code_dirs = [
+        Path("vulnerabilities/management/commands"),
+        Path("vulnerabilities/")
+    ]
+    for code_dir in code_dirs:
+        for path in code_dir.rglob('*.py'):
+            urls.extend(extract_urls(path.read_text()))
+    
+    return sorted({
+        url for url in urls
+        if is_valid_url(url) and url not in EXCLUDED_URLS
+    })
+
+@pytest.fixture(scope="module")
+def session():
+    """Configure HTTP session with enhanced retry logic"""
+    session = requests.Session()
+    retries = Retry(
+        total=MAX_RETRIES,
+        backoff_factor=1.5,
+        status_forcelist=[500, 502, 503, 504, 429],
+        allowed_methods=['HEAD', 'GET'],
+        respect_retry_after_header=True
+    )
+    session.mount('http://', HTTPAdapter(max_retries=retries))
+    session.mount('https://', HTTPAdapter(max_retries=retries))
+    return session
+
+@pytest.mark.parametrize("url", get_all_urls())
+def test_url_is_alive(url, session):
+    headers = {'User-Agent': USER_AGENT}
+    
+    try:
+        # Initial attempt with HEAD
+        try:
+            response = session.head(
+                url,
+                headers=headers,
+                allow_redirects=True,
+                timeout=TIMEOUT
+            )
+            if response.status_code == 405:
+                response = session.get(
+                    url,
+                    headers=headers,
+                    allow_redirects=True,
+                    timeout=TIMEOUT
+                )
+        except requests.exceptions.SSLError:
+            # Fallback to GET without SSL verification
+            response = session.get(
+                url,
+                headers=headers,
+                verify=False,
+                timeout=TIMEOUT
+            )
+        
+        # Handle special cases
+        if response.status_code in [403, 404] and url in EXCLUDED_URLS:
+            pytest.skip(f"Skipping excluded URL: {url}")
+            
+        if response.status_code == 403:
+            pytest.xfail(f"Expected 403 Forbidden for protected resource: {url}")
+            
+        assert 200 <= response.status_code < 400, \
+            f"URL {url} returned status {response.status_code}"
+            
+    except requests.exceptions.Timeout:
+        pytest.xfail(f"Timeout occurred for {url} - may be temporary")
+        
+    except requests.exceptions.RequestException as e:
+        if isinstance(e, requests.exceptions.ConnectionError):
+            if url in EXCLUDED_URLS:
+                pytest.skip(f"Skipping connection error for excluded URL: {url}")
+            pytest.xfail(f"Connection failed for {url} - possible network issue")
+            
+        pytest.fail(f"Failed to access {url}: {str(e)}")
+    
+    finally:
+        time.sleep(1)
\ No newline at end of file