diff --git a/lib/ruby_lsp/executor.rb b/lib/ruby_lsp/executor.rb
index a388788cf7..52db7ab625 100644
--- a/lib/ruby_lsp/executor.rb
+++ b/lib/ruby_lsp/executor.rb
@@ -188,14 +188,17 @@ def did_change_watched_files(changes)
         file_path = uri.to_standardized_path
         next if file_path.nil? || File.directory?(file_path)
 
+        base_path = $LOAD_PATH.find { |load_path| file_path.start_with?(load_path) }
+        indexable = RubyIndexer::Indexable.new(base_path, file_path)
+
         case change[:type]
         when Constant::FileChangeType::CREATED
-          @index.index_single(file_path)
+          @index.index_single(indexable)
         when Constant::FileChangeType::CHANGED
-          @index.delete(file_path)
-          @index.index_single(file_path)
+          @index.delete(indexable)
+          @index.index_single(indexable)
         when Constant::FileChangeType::DELETED
-          @index.delete(file_path)
+          @index.delete(indexable)
         end
       end