diff --git a/lib/herb/engine.rb b/lib/herb/engine.rb
index 69a9f8ee0..ce962d151 100644
--- a/lib/herb/engine.rb
+++ b/lib/herb/engine.rb
@@ -287,13 +287,9 @@ def add_expression_block_end(code, escaped: false)
       @src.chomp! if @src.end_with?("\n") && code_stripped.start_with?(" ")
 
       @src << " " << code_stripped
+      @src << "\n" if self.class.comment?(code_stripped)
       @src << (escaped ? "))" : ")")
-
-      @src << if code.include?("#") || trailing_newline
-                "\n"
-              else
-                ";"
-              end
+      @src << (trailing_newline ? "\n" : ";")
 
       @buffer_on_stack = false
     end
diff --git a/test/engine/engine_block_test.rb b/test/engine/engine_block_test.rb
index 641af9e44..417fca2b4 100644
--- a/test/engine/engine_block_test.rb
+++ b/test/engine/engine_block_test.rb
@@ -107,5 +107,11 @@ class EngineBlockTest < Minitest::Spec
 
       assert_compiled_snapshot(template)
     end
+
+    test "inline comment on end inside output block does not break parens" do
+      template = "<%= render Foo.new do %>hello<% end # comment %>"
+
+      assert_compiled_snapshot(template)
+    end
   end
 end
diff --git a/test/snapshots/engine/engine_block_test/test_0014_inline_comment_on_end_inside_output_block_does_not_break_parens_1c140392798ee0e334ac05bafcebe13b.txt b/test/snapshots/engine/engine_block_test/test_0014_inline_comment_on_end_inside_output_block_does_not_break_parens_1c140392798ee0e334ac05bafcebe13b.txt
new file mode 100644
index 000000000..fee742d04
--- /dev/null
+++ b/test/snapshots/engine/engine_block_test/test_0014_inline_comment_on_end_inside_output_block_does_not_break_parens_1c140392798ee0e334ac05bafcebe13b.txt
@@ -0,0 +1,7 @@
+---
+source: "Engine::EngineBlockTest#test_0014_inline comment on end inside output block does not break parens"
+input: "{source: \"<%= render Foo.new do %>hello<% end # comment %>\", options: {}}"
+---
+_buf = ::String.new; _buf << (render Foo.new do; _buf << 'hello'.freeze; end # comment
+);
+_buf.to_s