diff --git a/bootstraptest/test_yjit.rb b/bootstraptest/test_yjit.rb
index 31bb626690..1eb6e393e7 100644
--- a/bootstraptest/test_yjit.rb
+++ b/bootstraptest/test_yjit.rb
@@ -4859,3 +4859,38 @@ assert_equal '["raised", "Module", "Object"]', %q{
 
   ret += [foo(Class), foo(Class.new)]
 }
+
+# test TrueClass#=== before and after redefining TrueClass#==
+assert_equal '[[true, false, false], [true, true, false], [true, :error, :error]]', %q{
+  def true_eqq(x)
+    true === x
+  rescue NoMethodError
+    :error
+  end
+
+  def test
+    [
+      # first one is always true because rb_equal does object comparison before calling #==
+      true_eqq(true),
+      # these will use TrueClass#==
+      true_eqq(false),
+      true_eqq(:truthy),
+    ]
+  end
+
+  results = [test]
+
+  class TrueClass
+    def ==(x)
+      !x
+    end
+  end
+
+  results << test
+
+  class TrueClass
+    undef_method :==
+  end
+
+  results << test
+} unless rjit_enabled? # Not yet working on RJIT
diff --git a/yjit/bindgen/src/main.rs b/yjit/bindgen/src/main.rs
index 953ab0ac42..a7473c1bf6 100644
--- a/yjit/bindgen/src/main.rs
+++ b/yjit/bindgen/src/main.rs
@@ -380,6 +380,7 @@ fn main() {
 
         // From internal/object.h
         .allowlist_function("rb_class_allocate_instance")
+        .allowlist_function("rb_obj_equal")
 
         // From gc.h and internal/gc.h
         .allowlist_function("rb_obj_info")
diff --git a/yjit/src/codegen.rs b/yjit/src/codegen.rs
index 000f9fb516..62d6c085fb 100644
--- a/yjit/src/codegen.rs
+++ b/yjit/src/codegen.rs
@@ -250,6 +250,33 @@ impl JITState {
         }
     }
 
+    pub fn assume_expected_cfunc(
+        &mut self,
+        asm: &mut Assembler,
+        ocb: &mut OutlinedCb,
+        class: VALUE,
+        method: ID,
+        cfunc: *mut c_void,
+    ) -> bool {
+        let cme = unsafe { rb_callable_method_entry(class, method) };
+
+        if cme.is_null() {
+            return false;
+        }
+
+        let def_type = unsafe { get_cme_def_type(cme) };
+        if def_type != VM_METHOD_TYPE_CFUNC {
+            return false;
+        }
+        if unsafe { get_mct_func(get_cme_def_body_cfunc(cme)) } != cfunc {
+            return false;
+        }
+
+        self.assume_method_lookup_stable(asm, ocb, cme);
+
+        true
+    }
+
     pub fn assume_method_lookup_stable(&mut self, asm: &mut Assembler, ocb: &mut OutlinedCb, cme: CmePtr) -> Option<()> {
         jit_ensure_block_entry_exit(self, asm, ocb)?;
         self.method_lookup_assumptions.push(cme);
@@ -6164,6 +6191,34 @@ fn jit_rb_class_superclass(
     true
 }
 
+// Codegen for rb_trueclass_case_equal()
+fn jit_rb_trueclass_case_equal(
+    jit: &mut JITState,
+    asm: &mut Assembler,
+    ocb: &mut OutlinedCb,
+    _ci: *const rb_callinfo,
+    _cme: *const rb_callable_method_entry_t,
+    _block: Option<BlockHandler>,
+    _argc: i32,
+    _known_recv_class: Option<VALUE>,
+) -> bool {
+    if !jit.assume_expected_cfunc( asm, ocb, unsafe { rb_cTrueClass }, ID!(eq), rb_obj_equal as _) {
+        return false;
+    }
+
+    // Compare the arguments
+    asm_comment!(asm, "TrueClass#===");
+    let arg1 = asm.stack_pop(1);
+    let arg0 = asm.stack_pop(1);
+    asm.cmp(arg0, arg1);
+    let ret_opnd = asm.csel_e(Qtrue.into(), Qfalse.into());
+
+    let stack_ret = asm.stack_push(Type::UnknownImm);
+    asm.mov(stack_ret, ret_opnd);
+
+    true
+}
+
 fn jit_thread_s_current(
     _jit: &mut JITState,
     asm: &mut Assembler,
@@ -10166,6 +10221,8 @@ pub fn yjit_reg_method_codegen_fns() {
         yjit_reg_method(rb_cString, "<<", jit_rb_str_concat);
         yjit_reg_method(rb_cString, "+@", jit_rb_str_uplus);
 
+        yjit_reg_method(rb_cTrueClass, "===", jit_rb_trueclass_case_equal);
+
         yjit_reg_method(rb_cArray, "empty?", jit_rb_ary_empty_p);
         yjit_reg_method(rb_cArray, "length", jit_rb_ary_length);
         yjit_reg_method(rb_cArray, "size", jit_rb_ary_length);
diff --git a/yjit/src/cruby.rs b/yjit/src/cruby.rs
index d07262ad4f..9c44ed681f 100644
--- a/yjit/src/cruby.rs
+++ b/yjit/src/cruby.rs
@@ -805,6 +805,7 @@ pub(crate) mod ids {
         name: hash               content: b"hash"
         name: respond_to_missing content: b"respond_to_missing?"
         name: to_ary             content: b"to_ary"
+        name: eq                 content: b"=="
     }
 }
 
diff --git a/yjit/src/cruby_bindings.inc.rs b/yjit/src/cruby_bindings.inc.rs
index 70578ec7e9..a03c2d0f00 100644
--- a/yjit/src/cruby_bindings.inc.rs
+++ b/yjit/src/cruby_bindings.inc.rs
@@ -1024,6 +1024,7 @@ extern "C" {
     pub fn rb_attr_get(obj: VALUE, name: ID) -> VALUE;
     pub fn rb_obj_info_dump(obj: VALUE);
     pub fn rb_class_allocate_instance(klass: VALUE) -> VALUE;
+    pub fn rb_obj_equal(obj1: VALUE, obj2: VALUE) -> VALUE;
     pub fn rb_reg_new_ary(ary: VALUE, options: ::std::os::raw::c_int) -> VALUE;
     pub fn rb_ary_tmp_new_from_values(
         arg1: VALUE,