diff --git a/src/cortex-execpolicy/src/detection.rs b/src/cortex-execpolicy/src/detection.rs
index 3c8b8d854..2da6c0c6a 100644
--- a/src/cortex-execpolicy/src/detection.rs
+++ b/src/cortex-execpolicy/src/detection.rs
@@ -17,20 +17,20 @@ impl<'a> DetectionHelper<'a> {
 
     /// Normalize a path for comparison.
     pub fn normalize_path(path: &str) -> String {
-        let mut normalized = path.replace("//", "/");
+        let mut normalized = path.replace('\\', "/");
 
-        // Handle trailing slashes
-        while normalized.len() > 1 && normalized.ends_with('/') {
-            normalized.pop();
-        }
-
-        // Expand ~ to /home or user directory indicator
         if normalized.starts_with('~') {
             normalized = normalized.replacen('~', "/home", 1);
         }
 
-        // Handle Windows paths
-        normalized = normalized.replace('\\', "/");
+        while normalized.contains("//") {
+            normalized = normalized.replace("//", "/");
+        }
+
+        // Handle trailing slashes
+        while normalized.len() > 1 && normalized.ends_with('/') {
+            normalized.pop();
+        }
 
         normalized
     }
diff --git a/src/cortex-execpolicy/src/tests.rs b/src/cortex-execpolicy/src/tests.rs
index df773d2d6..d09e03273 100644
--- a/src/cortex-execpolicy/src/tests.rs
+++ b/src/cortex-execpolicy/src/tests.rs
@@ -72,6 +72,22 @@ mod decision_tests {
 mod parsed_command_tests {
     use super::*;
 
+    #[test]
+    fn test_normalize_path_collapses_repeated_slashes() {
+        assert_eq!(
+            crate::detection::DetectionHelper::normalize_path("///etc/shadow"),
+            "/etc/shadow"
+        );
+        assert_eq!(
+            crate::detection::DetectionHelper::normalize_path("////etc//passwd///"),
+            "/etc/passwd"
+        );
+        assert_eq!(
+            crate::detection::DetectionHelper::normalize_path(r"C:\\Users\\secrets\\"),
+            "C:/Users/secrets"
+        );
+    }
+
     #[test]
     fn test_parse_simple_command() {
         let cmd = ParsedCommand::from_args(&["ls".to_string(), "-la".to_string()]).unwrap();
@@ -254,6 +270,28 @@ mod destructive_file_ops_tests {
         }
     }
 
+    #[test]
+    fn test_multi_slash_sensitive_paths_denied() {
+        let policy = ExecPolicy::new();
+
+        let bypass_attempts = vec![
+            vec!["rm", "-rf", "///etc"],
+            vec!["rm", "-rf", "////etc/passwd"],
+            vec!["shred", "///etc/shadow"],
+            vec!["chmod", "777", "///etc/passwd"],
+        ];
+
+        for cmd in bypass_attempts {
+            let cmd_strings: Vec<String> = cmd.iter().map(|s| s.to_string()).collect();
+            assert_eq!(
+                policy.evaluate(&cmd_strings),
+                Decision::Deny,
+                "Failed for: {:?}",
+                cmd
+            );
+        }
+    }
+
     #[test]
     fn test_rm_on_safe_path_allowed() {
         let policy = ExecPolicy::new();