diff --git a/test/ruby/test_yjit.rb b/test/ruby/test_yjit.rb
index 6700e581768436..115c1902f0369d 100644
--- a/test/ruby/test_yjit.rb
+++ b/test/ruby/test_yjit.rb
@@ -1277,6 +1277,18 @@ def foo(a, b, h)
     RUBY
   end
 
+  def test_io_reopen_clobbering_singleton_class
+    assert_compiles(<<~RUBY, result: [:ok, :ok])
+      def $stderr.to_i = :i
+
+      def test = $stderr.to_i
+
+      [test, test]
+      $stderr.reopen($stderr.dup)
+      [test, test].map { :ok unless _1 == :i }
+    RUBY
+  end
+
   private
 
   def code_gc_helpers
diff --git a/yjit/bindgen/src/main.rs b/yjit/bindgen/src/main.rs
index 4fb02cfdf0799e..b9bef8e1768b68 100644
--- a/yjit/bindgen/src/main.rs
+++ b/yjit/bindgen/src/main.rs
@@ -165,6 +165,7 @@ fn main() {
         .allowlist_var("rb_cTrueClass")
         .allowlist_var("rb_cFalseClass")
         .allowlist_var("rb_cInteger")
+        .allowlist_var("rb_cIO")
         .allowlist_var("rb_cSymbol")
         .allowlist_var("rb_cFloat")
         .allowlist_var("rb_cString")
diff --git a/yjit/src/codegen.rs b/yjit/src/codegen.rs
index b64bdc0258110a..18d53fe65ebbae 100644
--- a/yjit/src/codegen.rs
+++ b/yjit/src/codegen.rs
@@ -3871,6 +3871,7 @@ fn jit_guard_known_klass(
     } else if unsafe {
         FL_TEST(known_klass, VALUE(RUBY_FL_SINGLETON as usize)) != VALUE(0)
             && sample_instance == rb_class_attached_object(known_klass)
+            && !rb_obj_is_kind_of(sample_instance, rb_cIO).test()
     } {
         // Singleton classes are attached to one specific object, so we can
         // avoid one memory access (and potentially the is_heap check) by
@@ -3882,6 +3883,8 @@ fn jit_guard_known_klass(
         // that its singleton class is empty, so we can't avoid the memory
         // access. As an example, `Object.new.singleton_class` is an object in
         // this situation.
+        // Also, guarding by identity is incorrect for IO objects because
+        // IO#reopen can be used to change the class and singleton class of IO objects!
         asm.comment("guard known object with singleton class");
         asm.cmp(obj_opnd, sample_instance.into());
         jit_chain_guard(JCC_JNE, jit, asm, ocb, max_chain_depth, counter);
diff --git a/yjit/src/cruby_bindings.inc.rs b/yjit/src/cruby_bindings.inc.rs
index 8415b444bae417..1f549161caf75e 100644
--- a/yjit/src/cruby_bindings.inc.rs
+++ b/yjit/src/cruby_bindings.inc.rs
@@ -1083,6 +1083,7 @@ extern "C" {
     pub static mut rb_cFalseClass: VALUE;
     pub static mut rb_cFloat: VALUE;
     pub static mut rb_cHash: VALUE;
+    pub static mut rb_cIO: VALUE;
     pub static mut rb_cInteger: VALUE;
     pub static mut rb_cModule: VALUE;
     pub static mut rb_cNilClass: VALUE;