diff --git a/litellm/proxy/_experimental/mcp_server/semantic_tool_filter.py b/litellm/proxy/_experimental/mcp_server/semantic_tool_filter.py
index 4412599dc0c..7530e5e2905 100644
--- a/litellm/proxy/_experimental/mcp_server/semantic_tool_filter.py
+++ b/litellm/proxy/_experimental/mcp_server/semantic_tool_filter.py
@@ -268,10 +268,19 @@ class SemanticMCPToolFilter:
         for canonical in tool_names:
             tool = available_by_name.get(canonical)
             if tool is None:
-                for client_name, candidate in available_by_name.items():
-                    if self._name_matches_canonical(client_name, canonical):
-                        tool = candidate
-                        break
+                # Prefer the shortest qualifying name. When several
+                # incoming tools suffix-match the same canonical (e.g.
+                # "my_search" and "my_tag_search" both end in "search"),
+                # the one closest in length to the canonical is the
+                # least-wrapped and most likely the intended target.
+                best_name: Optional[str] = None
+                for client_name in available_by_name:
+                    if not self._name_matches_canonical(client_name, canonical):
+                        continue
+                    if best_name is None or len(client_name) < len(best_name):
+                        best_name = client_name
+                if best_name is not None:
+                    tool = available_by_name[best_name]
             if tool is not None and id(tool) not in used_ids:
                 matched.append(tool)
                 used_ids.add(id(tool))
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_semantic_tool_filter.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_semantic_tool_filter.py
index 15917ff8a0f..97969ef9d8f 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_semantic_tool_filter.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_semantic_tool_filter.py
@@ -500,8 +500,10 @@ class TestGetToolsByNames:
 
     def test_same_tool_not_returned_twice(self):
         """
-        Two canonicals that both suffix-match the same incoming tool
-        must not produce a duplicate in the output list.
+        Two distinct canonicals that both suffix-match the same incoming
+        tool must not produce a duplicate in the output list.
+        ``read_file`` and ``file`` are both valid separator-anchored
+        suffixes of ``srv_read_file``.
         """
         filter_instance = self._make_filter()
         available_tools = [
@@ -509,11 +511,31 @@ class TestGetToolsByNames:
         ]
 
         matched = filter_instance._get_tools_by_names(
-            ["read_file", "read_file"], available_tools
+            ["read_file", "file"], available_tools
         )
 
         assert len(matched) == 1
 
+    def test_suffix_fallback_prefers_shortest_candidate(self):
+        """
+        When no exact match exists and several incoming tools
+        suffix-match the same canonical, the one closest in length to
+        the canonical (i.e. the least-wrapped) should be chosen.
+        """
+        filter_instance = self._make_filter()
+        canonical = "search"
+        available_tools = [
+            {"name": "my_tag_search", "description": "tag search"},
+            {"name": "my_search", "description": "plain search"},
+        ]
+
+        matched = filter_instance._get_tools_by_names(
+            [canonical], available_tools
+        )
+
+        assert len(matched) == 1
+        assert matched[0]["name"] == "my_search"
+
     def test_ordering_follows_router_output(self):
         """Returned tools follow the order the semantic router chose."""
         filter_instance = self._make_filter()