diff --git a/Lib/test/test_capi/test_opt.py b/Lib/test/test_capi/test_opt.py
index d80fec9a8a0d2b..839e1143852f7f 100644
--- a/Lib/test/test_capi/test_opt.py
+++ b/Lib/test/test_capi/test_opt.py
@@ -6137,6 +6137,20 @@ def __init__(self, x):
                 C(0) if i else str(0)
         """))
 
+    def test_load_special_type_guard_deopt(self):
+        script_helper.assert_python_ok("-s", "-c", textwrap.dedent(f"""
+            def f1():
+                class Context:
+                    def __enter__(self): ...
+                    def __exit__(self, e, v, t): ...
+
+                with Context():
+                    pass
+
+            for _ in range({TIER2_THRESHOLD + 5}):
+                f1()
+        """), PYTHON_JIT="1")
+
 def global_identity(x):
     return x
 
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-05-07-03-18-59.gh-issue-149459.5fhAqP.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-05-07-03-18-59.gh-issue-149459.5fhAqP.rst
new file mode 100644
index 00000000000000..4cd0a148df3c70
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2026-05-07-03-18-59.gh-issue-149459.5fhAqP.rst
@@ -0,0 +1 @@
+Fix a crash in the JIT optimizer when a specialized ``LOAD_SPECIAL`` guard deoptimized after inserting the synthetic ``NULL`` stack entry.
diff --git a/Python/optimizer_bytecodes.c b/Python/optimizer_bytecodes.c
index e10a096baa3318..76020c66c7be58 100644
--- a/Python/optimizer_bytecodes.c
+++ b/Python/optimizer_bytecodes.c
@@ -2041,7 +2041,16 @@ dummy_func(void) {
             PyObject *name = _Py_SpecialMethods[oparg].name;
             PyObject *descr = _PyType_Lookup(type, name);
             if (descr != NULL && (Py_TYPE(descr)->tp_flags & Py_TPFLAGS_METHOD_DESCRIPTOR)) {
-                ADD_OP(_GUARD_TYPE_VERSION, 0, type->tp_version_tag);
+                /* LOAD_SPECIAL expands to _RECORD_TOS_TYPE + _INSERT_NULL +
+                 * _LOAD_SPECIAL. Insert _GUARD_TYPE_VERSION before the
+                 * already-emitted _INSERT_NULL so deopt sees the original
+                 * stack shape.*/
+                _PyUOpInstruction *insert_null = uop_buffer_last(&ctx->out_buffer);
+                assert(insert_null->opcode == _INSERT_NULL);
+                assert(insert_null->target == this_instr->target);
+                REPLACE_OP(insert_null, _GUARD_TYPE_VERSION, 0, type->tp_version_tag);
+                ADD_OP(_INSERT_NULL, 0, 0);
+
                 bool immortal = _Py_IsImmortal(descr) || (type->tp_flags & Py_TPFLAGS_IMMUTABLETYPE);
                 ADD_OP(immortal ? _LOAD_CONST_INLINE_BORROW : _LOAD_CONST_INLINE,
                        0, (uintptr_t)descr);
diff --git a/Python/optimizer_cases.c.h b/Python/optimizer_cases.c.h
index 01ecb3790aa2cd..5b803b0ac0d241 100644
--- a/Python/optimizer_cases.c.h
+++ b/Python/optimizer_cases.c.h
@@ -3895,7 +3895,11 @@
                 PyObject *name = _Py_SpecialMethods[oparg].name;
                 PyObject *descr = _PyType_Lookup(type, name);
                 if (descr != NULL && (Py_TYPE(descr)->tp_flags & Py_TPFLAGS_METHOD_DESCRIPTOR)) {
-                    ADD_OP(_GUARD_TYPE_VERSION, 0, type->tp_version_tag);
+                    _PyUOpInstruction *insert_null = uop_buffer_last(&ctx->out_buffer);
+                    assert(insert_null->opcode == _INSERT_NULL);
+                    assert(insert_null->target == this_instr->target);
+                    REPLACE_OP(insert_null, _GUARD_TYPE_VERSION, 0, type->tp_version_tag);
+                    ADD_OP(_INSERT_NULL, 0, 0);
                     bool immortal = _Py_IsImmortal(descr) || (type->tp_flags & Py_TPFLAGS_IMMUTABLETYPE);
                     ADD_OP(immortal ? _LOAD_CONST_INLINE_BORROW : _LOAD_CONST_INLINE,
                         0, (uintptr_t)descr);