diff --git a/lib/steep/services/type_check_service.rb b/lib/steep/services/type_check_service.rb
index 3f91e841..1c2fd4fd 100644
--- a/lib/steep/services/type_check_service.rb
+++ b/lib/steep/services/type_check_service.rb
@@ -302,7 +302,22 @@ def type_check_file(target:, subtyping:, path:, text:)
       def self.type_check(source:, subtyping:, constant_resolver:, cursor:)
         annotations = source.annotations(block: source.node, factory: subtyping.factory, context: nil)
 
-        definition = subtyping.factory.definition_builder.build_instance(AST::Builtin::Object.module_name)
+        case annotations.self_type
+        when AST::Types::Name::Instance
+          module_name = annotations.self_type.name
+          module_type = AST::Types::Name::Singleton.new(name: module_name)
+          instance_type = annotations.self_type
+        when AST::Types::Name::Singleton
+          module_name = annotations.self_type.name
+          module_type = annotations.self_type
+          instance_type = annotations.self_type
+        else
+          module_name = AST::Builtin::Object.module_name
+          module_type = AST::Builtin::Object.module_type
+          instance_type = AST::Builtin::Object.instance_type
+        end
+
+        definition = subtyping.factory.definition_builder.build_instance(module_name)
 
         const_env = TypeInference::ConstantEnv.new(
           factory: subtyping.factory,
@@ -321,17 +336,17 @@ def self.type_check(source:, subtyping:, constant_resolver:, cursor:)
         context = TypeInference::Context.new(
           block_context: nil,
           module_context: TypeInference::Context::ModuleContext.new(
-            instance_type: AST::Builtin::Object.instance_type,
-            module_type: AST::Builtin::Object.module_type,
+            instance_type: instance_type,
+            module_type: module_type,
             implement_name: nil,
             nesting: nil,
-            class_name: AST::Builtin::Object.module_name,
-            instance_definition: subtyping.factory.definition_builder.build_instance(AST::Builtin::Object.module_name),
-            module_definition: subtyping.factory.definition_builder.build_singleton(AST::Builtin::Object.module_name)
+            class_name: module_name,
+            instance_definition: subtyping.factory.definition_builder.build_instance(module_name),
+            module_definition: subtyping.factory.definition_builder.build_singleton(module_name)
           ),
           method_context: nil,
           break_context: nil,
-          self_type: AST::Builtin::Object.instance_type,
+          self_type: instance_type,
           type_env: type_env,
           call_context: TypeInference::MethodCall::TopLevelContext.new,
           variable_context: TypeInference::Context::TypeVariableContext.empty
diff --git a/smoke/toplevel_annotations/Steepfile b/smoke/toplevel_annotations/Steepfile
new file mode 100644
index 00000000..2a84dd11
--- /dev/null
+++ b/smoke/toplevel_annotations/Steepfile
@@ -0,0 +1,7 @@
+target :test do
+  check "*.rb"
+
+  implicitly_returns_nil! true
+
+  configure_code_diagnostics(Steep::Diagnostic::Ruby.all_error)
+end
diff --git a/smoke/toplevel_annotations/a.rb b/smoke/toplevel_annotations/a.rb
new file mode 100644
index 00000000..175ad617
--- /dev/null
+++ b/smoke/toplevel_annotations/a.rb
@@ -0,0 +1,7 @@
+# @type self: String
+
+succ
+to_s
+each_line do |line|
+  puts line
+end
diff --git a/smoke/toplevel_annotations/test_expectations.yml b/smoke/toplevel_annotations/test_expectations.yml
new file mode 100644
index 00000000..dcd024e9
--- /dev/null
+++ b/smoke/toplevel_annotations/test_expectations.yml
@@ -0,0 +1 @@
+--- []
diff --git a/test/test_helper.rb b/test/test_helper.rb
index f4745e7b..2abcb3b2 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -624,12 +624,25 @@ module TypeConstructionHelper
 
   # @rbs (Subtyping::Check, Source, ?cursor: untyped) { (TypeConstruction, Typing) -> void } -> void
   def with_standard_construction(checker, source, cursor: nil)
-    self_type = parse_type("::Object")
-
     annotations = source.annotations(block: source.node, factory: checker.factory, context: nil)
     resolver = RBS::Resolver::ConstantResolver.new(builder: checker.factory.definition_builder)
     const_env = ConstantEnv.new(factory: checker.factory, context: nil, resolver: resolver)
 
+    case annotations.self_type
+    when AST::Types::Name::Instance
+      module_name = annotations.self_type.name
+      module_type = AST::Types::Name::Singleton.new(name: module_name)
+      instance_type = annotations.self_type
+    when AST::Types::Name::Singleton
+      module_name = annotations.self_type.name
+      module_type = annotations.self_type
+      instance_type = annotations.self_type
+    else
+      module_name = AST::Builtin::Object.module_name
+      module_type = AST::Builtin::Object.module_type
+      instance_type = AST::Builtin::Object.instance_type
+    end
+
     rbs_env = checker.factory.env
     type_env = Steep::TypeInference::TypeEnvBuilder.new(
       Steep::TypeInference::TypeEnvBuilder::Command::ImportGlobalDeclarations.new(checker.factory),
@@ -642,16 +655,16 @@ def with_standard_construction(checker, source, cursor: nil)
       block_context: nil,
       method_context: nil,
       module_context: Context::ModuleContext.new(
-        instance_type: AST::Builtin::Object.instance_type,
-        module_type: AST::Builtin::Object.module_type,
+        instance_type: instance_type,
+        module_type: module_type,
         implement_name: nil,
         nesting: nil,
-        class_name: AST::Builtin::Object.module_name,
-        instance_definition: checker.factory.definition_builder.build_instance(AST::Builtin::Object.module_name),
-        module_definition: checker.factory.definition_builder.build_singleton(AST::Builtin::Object.module_name)
+        class_name: module_name,
+        instance_definition: checker.factory.definition_builder.build_instance(module_name),
+        module_definition: checker.factory.definition_builder.build_singleton(module_name)
       ),
       break_context: nil,
-      self_type: self_type,
+      self_type: instance_type,
       type_env: type_env,
       call_context: TypeInference::MethodCall::TopLevelContext.new(),
       variable_context: Context::TypeVariableContext.empty