diff --git a/.jules/sentinel.md b/.jules/sentinel.md
index 6a6144c5..b108555f 100644
--- a/.jules/sentinel.md
+++ b/.jules/sentinel.md
@@ -19,3 +19,7 @@
 **Vulnerability:** The `_test_imap_connection` and `_test_s3_connection` functions in `app/api/integrations.py` did not validate user-provided `host` and `endpoint_url` variables against `is_private_ip()`. This allowed an attacker to test the presence of internal IMAP servers or direct S3 SDK API calls to internal infrastructure via SSRF.
 **Learning:** Any time a new generic connection or integration test is added, SSRF validation may be forgotten if the core network utility (`is_private_ip`) is not systematically applied to all outbound network operations, regardless of the protocol (e.g., IMAP, S3).
 **Prevention:** Establish a pattern where any user-configurable host or endpoint URL is immediately passed through the centralized `is_private_ip` validation function before any network call or third-party client initialization.
+## 2026-03-27 - SSRF Bypass via HTTP Redirects in httpx
+**Vulnerability:** The `/process-url` endpoint used `httpx.AsyncClient(follow_redirects=True)` after validating the initial user-provided URL against SSRF protections. However, it did not validate the target URLs of any subsequent HTTP redirects, allowing an attacker to provide a safe URL that redirects to an internal/private IP, bypassing the security check.
+**Learning:** Initial URL validation is insufficient when the HTTP client is configured to follow redirects automatically. The client must be explicitly configured to validate every redirect target.
+**Prevention:** When using `httpx.AsyncClient(follow_redirects=True)` for user-provided URLs, always implement a redirect validator hook function (e.g., using `event_hooks={'response': [validate_redirect]}`) that resolves the `Location` header and passes it through the same SSRF validation logic before the redirect is followed.
diff --git a/app/api/url_upload.py b/app/api/url_upload.py
index e93eaea3..91cc3a06 100644
--- a/app/api/url_upload.py
+++ b/app/api/url_upload.py
@@ -151,6 +151,19 @@ async def process_url(
     if not safe_filename:
         safe_filename = "download"
 
+    # Hook to validate redirects and prevent SSRF
+    async def validate_redirect(response: httpx.Response):
+        if response.is_redirect:
+            location = response.headers.get("Location")
+            if location:
+                # Resolve relative URLs
+                next_url = urllib.parse.urljoin(str(response.url), location)
+                try:
+                    validate_url_safety(next_url)
+                except HTTPException as e:
+                    # Reraise as a RequestError so httpx aborts the request
+                    raise httpx.RequestError(f"Unsafe redirect target: {e.detail}", request=response.request)
+
     # Download file with security measures
     # Initialize target_path to None to prevent UnboundLocalError in exception handlers
     # that may execute before target_path is assigned during error cases
@@ -162,6 +175,7 @@ async def process_url(
         async with httpx.AsyncClient(
             timeout=settings.http_request_timeout,
             follow_redirects=True,
+            event_hooks={"response": [validate_redirect]},
             headers={
                 "User-Agent": "DocuElevate/1.0",  # Identify ourselves
             },