diff --git a/test/custom_importer_test.rb b/test/custom_importer_test.rb
index dfb556c..1e4ce52 100644
--- a/test/custom_importer_test.rb
+++ b/test/custom_importer_test.rb
@@ -37,6 +37,16 @@ def imports(_path, parent_path)
       end
     end
 
+    class ParentDirImporter < Importer
+      def imports(path, parent_path)
+        if path.include?('path')
+          Import.new('path.scss', source: "a { from: #{File.basename(File.dirname(parent_path))}; }")
+        else
+          Import.new(path)
+        end
+      end
+    end
+
     def test_custom_importer_works
       temp_file('styles2.scss', '.hi { color: $var1; }')
       temp_file('fonts.scss', '.font { color: $var1; }')
@@ -87,6 +97,33 @@ def test_custom_importer_works_for_file_in_parent_dir
       CSS
     end
 
+    # regression test for https://github.com/sass/dart-sass/issues/2208
+    def test_custom_importer_works_for_imports_with_same_name
+      temp_dir('sub1')
+      temp_dir('sub1/sub2')
+      temp_file('sub1/test.scss', '@import "path";')
+      temp_file('sub1/sub2/test.scss', '@import "path";')
+
+      data = <<~SCSS
+        @import "sub1/test";
+        @import "sub1/sub2/test";
+      SCSS
+
+      engine = Engine.new(data, {
+                            importer: ParentDirImporter
+                          })
+
+      assert_equal <<~CSS, engine.render
+        a {
+          from: sub1;
+        }
+
+        a {
+          from: sub2;
+        }
+      CSS
+    end
+
     def test_dependency_list
       base = Dir.pwd