diff --git a/nemoguardrails/library/jailbreak_detection/request.py b/nemoguardrails/library/jailbreak_detection/request.py
index 64d5a0b1a..933381457 100644
--- a/nemoguardrails/library/jailbreak_detection/request.py
+++ b/nemoguardrails/library/jailbreak_detection/request.py
@@ -31,12 +31,30 @@
 import asyncio
 import logging
 from typing import Optional
+from urllib.parse import urljoin
 
 import aiohttp
 
 log = logging.getLogger(__name__)
 
 
+def join_nim_url(base_url: str, classification_path: str) -> str:
+    """Join NIM base URL with classification path, handling trailing/leading slashes.
+
+    Args:
+        base_url: The base NIM URL (with or without trailing slash)
+        classification_path: The classification endpoint path (with or without leading slash)
+
+    Returns:
+        Properly joined URL
+    """
+    # Ensure base_url ends with '/' for proper urljoin behavior
+    normalized_base = base_url.rstrip("/") + "/"
+    # Remove leading slash from classification path to ensure relative joining
+    normalized_path = classification_path.lstrip("/")
+    return urljoin(normalized_base, normalized_path)
+
+
 async def jailbreak_detection_heuristics_request(
     prompt: str,
     api_url: str = "http://localhost:1337/heuristics",
@@ -101,14 +119,12 @@ async def jailbreak_nim_request(
     nim_auth_token: Optional[str],
     nim_classification_path: str,
 ):
-    from urllib.parse import urljoin
-
     headers = {"Content-Type": "application/json", "Accept": "application/json"}
     payload = {
         "input": prompt,
     }
 
-    endpoint = urljoin(nim_url, nim_classification_path)
+    endpoint = join_nim_url(nim_url, nim_classification_path)
     try:
         async with aiohttp.ClientSession() as session:
             try:
diff --git a/tests/test_jailbreak_request.py b/tests/test_jailbreak_request.py
index c5227d516..54ea997d1 100644
--- a/tests/test_jailbreak_request.py
+++ b/tests/test_jailbreak_request.py
@@ -25,31 +25,51 @@ class TestJailbreakRequestChanges:
     """Test jailbreak request function changes introduced in this PR."""
 
     def test_url_joining_logic(self):
-        """Test that URL joining works correctly using urljoin."""
+        """Test that URL joining works correctly with all slash combinations."""
+        from nemoguardrails.library.jailbreak_detection.request import join_nim_url
+
         test_cases = [
             (
                 "http://localhost:8000/v1",
                 "classify",
-                "http://localhost:8000/classify",
-            ),  # v1 replaced by classify
+                "http://localhost:8000/v1/classify",
+            ),
             (
                 "http://localhost:8000/v1/",
                 "classify",
                 "http://localhost:8000/v1/classify",
-            ),  # trailing slash preserves v1
+            ),
+            (
+                "http://localhost:8000/v1",
+                "/classify",
+                "http://localhost:8000/v1/classify",
+            ),
             (
-                "http://localhost:8000",
-                "v1/classify",
+                "http://localhost:8000/v1/",
+                "/classify",
                 "http://localhost:8000/v1/classify",
             ),
+            ("http://localhost:8000", "classify", "http://localhost:8000/classify"),
+            ("http://localhost:8000", "/classify", "http://localhost:8000/classify"),
+            ("http://localhost:8000/", "classify", "http://localhost:8000/classify"),
             ("http://localhost:8000/", "/classify", "http://localhost:8000/classify"),
+            (
+                "http://localhost:8000/api/v1",
+                "classify",
+                "http://localhost:8000/api/v1/classify",
+            ),
+            (
+                "http://localhost:8000/api/v1/",
+                "/classify",
+                "http://localhost:8000/api/v1/classify",
+            ),
         ]
 
-        for base_url, path, expected_url in test_cases:
-            result = urljoin(base_url, path)
+        for base_url, classification_path, expected_url in test_cases:
+            result = join_nim_url(base_url, classification_path)
             assert (
                 result == expected_url
-            ), f"urljoin({base_url}, {path}) should equal {expected_url}"
+            ), f"join_nim_url({base_url}, {classification_path}) should equal {expected_url}, got {result}"
 
     def test_auth_header_logic(self):
         """Test the authorization header logic."""