diff --git a/aikido_zen/__init__.py b/aikido_zen/__init__.py
index 2458a16b3..440288e88 100644
--- a/aikido_zen/__init__.py
+++ b/aikido_zen/__init__.py
@@ -71,6 +71,7 @@ def protect(mode="daemon", token=""):
 
     import aikido_zen.sinks.builtins
     import aikido_zen.sinks.os
+    import aikido_zen.sinks.pathlib
     import aikido_zen.sinks.shutil
     import aikido_zen.sinks.io
     import aikido_zen.sinks.http_client
diff --git a/aikido_zen/sinks/pathlib.py b/aikido_zen/sinks/pathlib.py
new file mode 100644
index 000000000..d3874ae36
--- /dev/null
+++ b/aikido_zen/sinks/pathlib.py
@@ -0,0 +1,29 @@
+"""
+Sink module for python's `pathlib`
+"""
+
+import aikido_zen.vulnerabilities as vulns
+from aikido_zen.helpers.get_argument import get_argument
+from aikido_zen.helpers.register_call import register_call
+from aikido_zen.sinks import before, patch_function, on_import
+
+
+@before
+def _pathlib_truediv_patch(func, instance, args, kwargs):
+    path = get_argument(args, kwargs, 0, "key")
+    op = "pathlib.PurePath.__truediv__"
+    register_call(op, "fs_op")
+
+    vulns.run_vulnerability_scan(kind="path_traversal", op=op, args=(path,))
+
+
+@on_import("pathlib")
+def patch(m):
+    """
+    patching module pathlib
+    - patches PurePath.__truediv__ : Path() / Path() -> join operation
+    """
+
+    # PurePath() / "my/path/test.txt"
+    # This is accomplished by overloading the __truediv__ function on the Path class
+    patch_function(m, "PurePath.__truediv__", _pathlib_truediv_patch)
diff --git a/aikido_zen/sinks/tests/os_test.py b/aikido_zen/sinks/tests/os_test.py
index fc55f66fc..387d4d00b 100644
--- a/aikido_zen/sinks/tests/os_test.py
+++ b/aikido_zen/sinks/tests/os_test.py
@@ -1,11 +1,45 @@
 import pytest
 from pathlib import Path, PurePath
 from unittest.mock import patch
-import aikido_zen.sinks.os
+import aikido_zen
+
+aikido_zen.protect()
+from aikido_zen.context import Context
+from aikido_zen.errors import AikidoPathTraversal
+from aikido_zen.sinks.tests.clickhouse_driver_test import set_blocking_to_true
 
 kind = "path_traversal"
 
 
+def set_context(param):
+    wsgi_request = {
+        "REQUEST_METHOD": "GET",
+        "HTTP_HEADER_1": "header 1 value",
+        "HTTP_HEADER_2": "Header 2 value",
+        "RANDOM_VALUE": "Random value",
+        "HTTP_COOKIE": "sessionId=abc123xyz456;",
+        "wsgi.url_scheme": "http",
+        "HTTP_HOST": "localhost:8080",
+        "PATH_INFO": "/hello",
+        "QUERY_STRING": "user=JohnDoe&age=30&age=35",
+        "CONTENT_TYPE": "application/json",
+        "REMOTE_ADDR": "198.51.100.23",
+    }
+    context = Context(
+        req=wsgi_request,
+        body={
+            "param": param,
+        },
+        source="flask",
+    )
+    context.set_as_current_context()
+
+
+@pytest.fixture(autouse=True)
+def set_blocking_to_true(monkeypatch):
+    monkeypatch.setenv("AIKIDO_BLOCK", "1")
+
+
 def test_ospath_commands():
     with patch(
         "aikido_zen.vulnerabilities.run_vulnerability_scan"
@@ -39,6 +73,36 @@ def test_ospath_commands():
         mock_run_vulnerability_scan.assert_any_call(kind=kind, op=op, args=args)
 
 
+def test_os_create_path_with_multiple_slashes():
+    import os
+
+    file_path = "////etc/passwd"
+    set_context(file_path)
+    with pytest.raises(AikidoPathTraversal):
+        full_path = Path("flaskr/resources/blogs/") / file_path
+        open(full_path, "r").close()
+
+
+def test_os_create_path_with_multiple_double_slashes():
+    import os
+
+    file_path = "////etc//passwd"
+    set_context(file_path)
+    with pytest.raises(AikidoPathTraversal):
+        full_path = Path("flaskr/resources/blogs/") / file_path
+        open(full_path, "r").close()
+
+
+def test_os_path_traversal_with_multiple_slashes():
+    import os
+
+    file_path = "home///..////..////my_secret.txt"
+    set_context(file_path)
+    with pytest.raises(AikidoPathTraversal):
+        full_path = Path("flaskr/resources/blogs/") / file_path
+        open(full_path, "r").close()
+
+
 def test_ospath_command_absolute_path():
     with patch(
         "aikido_zen.vulnerabilities.run_vulnerability_scan"
diff --git a/aikido_zen/vulnerabilities/path_traversal/unsafe_path_start.py b/aikido_zen/vulnerabilities/path_traversal/unsafe_path_start.py
index 541ee763e..7e6868cd5 100644
--- a/aikido_zen/vulnerabilities/path_traversal/unsafe_path_start.py
+++ b/aikido_zen/vulnerabilities/path_traversal/unsafe_path_start.py
@@ -28,13 +28,19 @@
 
 def starts_with_unsafe_path(file_path, user_input):
     """Check if the file path starts with any dangerous paths and the user input."""
-    lower_case_path = file_path.lower()
-    lower_case_user_input = user_input.lower()
+    path_parsed = ensure_one_leading_slash(file_path.lower())
+    input_parsed = ensure_one_leading_slash(user_input.lower())
 
     for dangerous_start in dangerous_path_starts:
-        if lower_case_path.startswith(dangerous_start) and lower_case_path.startswith(
-            lower_case_user_input
+        if path_parsed.startswith(dangerous_start) and path_parsed.startswith(
+            input_parsed
         ):
             return True
 
     return False
+
+
+def ensure_one_leading_slash(path: str) -> str:
+    if path.startswith("/"):
+        return "/" + path.lstrip("/")
+    return path