diff --git a/pylsp/_utils.py b/pylsp/_utils.py
index dfe84b14..1267fd83 100644
--- a/pylsp/_utils.py
+++ b/pylsp/_utils.py
@@ -134,9 +134,17 @@ def match_uri_to_workspace(uri, workspaces):
         if len(workspace_parts) > len(path):
             continue
         match_len = 0
+        is_parent = True
         for workspace_part, path_part in zip(workspace_parts, path):
             if workspace_part == path_part:
                 match_len += 1
+            else:
+                is_parent = False
+                break
+        # prefer a match that is actually a parent of uri
+        # otherwise fall back to longest matching non-parent
+        if is_parent and match_len > 0:
+            match_len += 1000
         if match_len > 0:
             if match_len > max_len:
                 max_len = match_len