diff --git a/core/path_mapper.py b/core/path_mapper.py
index 2b3480a..0b1a9d2 100644
--- a/core/path_mapper.py
+++ b/core/path_mapper.py
@@ -25,15 +25,28 @@ class PathMapper:
     
     def sonarr_path_to_container_path(self, sonarr_path: str) -> str:
         """Convert Sonarr path to container path using environment mappings"""
-        # Try to match against configured Sonarr root folders
-        for i, sonarr_root in enumerate(self.sonarr_roots):
-            if sonarr_path.startswith(sonarr_root):
-                # Map to corresponding TV path
-                if i < len(self.tv_paths):
-                    container_root = self.tv_paths[i]
-                    relative_path = sonarr_path[len(sonarr_root):].lstrip('/')
-                    return str(Path(container_root) / relative_path) if relative_path else container_root
+        print(f"DEBUG: sonarr_path_to_container_path input: {sonarr_path}")
+        print(f"DEBUG: sonarr_roots: {self.sonarr_roots}")
+        print(f"DEBUG: tv_paths: {self.tv_paths}")
         
+        # Sort roots by length (longest first) to avoid substring matching issues
+        indexed_roots = [(i, root) for i, root in enumerate(self.sonarr_roots)]
+        indexed_roots.sort(key=lambda x: len(x[1]), reverse=True)
+        
+        # Try to match against configured Sonarr root folders (longest first)
+        for original_index, sonarr_root in indexed_roots:
+            print(f"DEBUG: Checking sonarr_root[{original_index}]: {sonarr_root}")
+            if sonarr_path.startswith(sonarr_root + '/') or sonarr_path == sonarr_root:
+                print(f"DEBUG: Match found! Index {original_index}")
+                # Map to corresponding TV path
+                if original_index < len(self.tv_paths):
+                    container_root = self.tv_paths[original_index]
+                    relative_path = sonarr_path[len(sonarr_root):].lstrip('/')
+                    result = str(Path(container_root) / relative_path) if relative_path else container_root
+                    print(f"DEBUG: Mapped to: {result}")
+                    return result
+        
+        print(f"DEBUG: No match found, returning original: {sonarr_path}")
         # No fallback - if path mapping fails, return original and let validation catch it
         return sonarr_path
     
@@ -43,14 +56,18 @@ class PathMapper:
         print(f"DEBUG: radarr_roots: {self.radarr_roots}")
         print(f"DEBUG: movie_paths: {self.movie_paths}")
         
-        # Try to match against configured Radarr root folders
-        for i, radarr_root in enumerate(self.radarr_roots):
-            print(f"DEBUG: Checking radarr_root[{i}]: {radarr_root}")
-            if radarr_path.startswith(radarr_root):
-                print(f"DEBUG: Match found! Index {i}")
+        # Sort roots by length (longest first) to avoid substring matching issues
+        indexed_roots = [(i, root) for i, root in enumerate(self.radarr_roots)]
+        indexed_roots.sort(key=lambda x: len(x[1]), reverse=True)
+        
+        # Try to match against configured Radarr root folders (longest first)
+        for original_index, radarr_root in indexed_roots:
+            print(f"DEBUG: Checking radarr_root[{original_index}]: {radarr_root}")
+            if radarr_path.startswith(radarr_root + '/') or radarr_path == radarr_root:
+                print(f"DEBUG: Match found! Index {original_index}")
                 # Map to corresponding movie path
-                if i < len(self.movie_paths):
-                    container_root = self.movie_paths[i]
+                if original_index < len(self.movie_paths):
+                    container_root = self.movie_paths[original_index]
                     relative_path = radarr_path[len(radarr_root):].lstrip('/')
                     result = str(Path(container_root) / relative_path) if relative_path else container_root
                     print(f"DEBUG: Mapped to: {result}")