diff --git a/Include/internal/pycore_opcode_metadata.h b/Include/internal/pycore_opcode_metadata.h
index 5b0d8dfd1b0..bbba0bbbf4b 100644
--- a/Include/internal/pycore_opcode_metadata.h
+++ b/Include/internal/pycore_opcode_metadata.h
@@ -1161,10 +1161,10 @@ const struct opcode_metadata _PyOpcode_opcode_metadata[268] = {
     [TO_BOOL] = { true, INSTR_FMT_IXC00, HAS_ERROR_FLAG | HAS_ESCAPES_FLAG },
     [TO_BOOL_ALWAYS_TRUE] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG },
     [TO_BOOL_BOOL] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG },
-    [TO_BOOL_INT] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG },
+    [TO_BOOL_INT] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG | HAS_ESCAPES_FLAG },
     [TO_BOOL_LIST] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG },
     [TO_BOOL_NONE] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG },
-    [TO_BOOL_STR] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG },
+    [TO_BOOL_STR] = { true, INSTR_FMT_IXC00, HAS_EXIT_FLAG | HAS_ESCAPES_FLAG },
     [UNARY_INVERT] = { true, INSTR_FMT_IX, HAS_ERROR_FLAG | HAS_ESCAPES_FLAG },
     [UNARY_NEGATIVE] = { true, INSTR_FMT_IX, HAS_ERROR_FLAG | HAS_ESCAPES_FLAG },
     [UNARY_NOT] = { true, INSTR_FMT_IX, HAS_PURE_FLAG },
diff --git a/Include/internal/pycore_uop_metadata.h b/Include/internal/pycore_uop_metadata.h
index bc0ba16e24f..02ffc769c18 100644
--- a/Include/internal/pycore_uop_metadata.h
+++ b/Include/internal/pycore_uop_metadata.h
@@ -52,10 +52,10 @@ const uint16_t _PyUop_Flags[MAX_UOP_ID+1] = {
     [_UNARY_NOT] = HAS_PURE_FLAG,
     [_TO_BOOL] = HAS_ERROR_FLAG | HAS_ESCAPES_FLAG,
     [_TO_BOOL_BOOL] = HAS_EXIT_FLAG,
-    [_TO_BOOL_INT] = HAS_EXIT_FLAG,
+    [_TO_BOOL_INT] = HAS_EXIT_FLAG | HAS_ESCAPES_FLAG,
     [_TO_BOOL_LIST] = HAS_EXIT_FLAG,
     [_TO_BOOL_NONE] = HAS_EXIT_FLAG,
-    [_TO_BOOL_STR] = HAS_EXIT_FLAG,
+    [_TO_BOOL_STR] = HAS_EXIT_FLAG | HAS_ESCAPES_FLAG,
     [_REPLACE_WITH_TRUE] = 0,
     [_UNARY_INVERT] = HAS_ERROR_FLAG | HAS_ESCAPES_FLAG,
     [_GUARD_BOTH_INT] = HAS_EXIT_FLAG,
diff --git a/Objects/bytesobject.c b/Objects/bytesobject.c
index cd799a926ae..b8bcef27cf1 100644
--- a/Objects/bytesobject.c
+++ b/Objects/bytesobject.c
@@ -46,7 +46,7 @@ Py_LOCAL_INLINE(Py_ssize_t) _PyBytesWriter_GetSize(_PyBytesWriter *writer,
 static inline PyObject* bytes_get_empty(void)
 {
     PyObject *empty = &EMPTY->ob_base.ob_base;
-    assert(_Py_IsImmortal(empty));
+    assert(_Py_IsImmortalLoose(empty));
     return empty;
 }
 
@@ -119,7 +119,7 @@ PyBytes_FromStringAndSize(const char *str, Py_ssize_t size)
     }
     if (size == 1 && str != NULL) {
         op = CHARACTER(*str & 255);
-        assert(_Py_IsImmortal(op));
+        assert(_Py_IsImmortalLoose(op));
         return (PyObject *)op;
     }
     if (size == 0) {
@@ -155,7 +155,7 @@ PyBytes_FromString(const char *str)
     }
     else if (size == 1) {
         op = CHARACTER(*str & 255);
-        assert(_Py_IsImmortal(op));
+        assert(_Py_IsImmortalLoose(op));
         return (PyObject *)op;
     }
 
diff --git a/Objects/typeobject.c b/Objects/typeobject.c
index 3386eb0105e..16acb8b682d 100644
--- a/Objects/typeobject.c
+++ b/Objects/typeobject.c
@@ -452,7 +452,7 @@ set_tp_bases(PyTypeObject *self, PyObject *bases, int initial)
             assert(PyTuple_GET_SIZE(bases) == 1);
             assert(PyTuple_GET_ITEM(bases, 0) == (PyObject *)self->tp_base);
             assert(self->tp_base->tp_flags & _Py_TPFLAGS_STATIC_BUILTIN);
-            assert(_Py_IsImmortal(self->tp_base));
+            assert(_Py_IsImmortalLoose(self->tp_base));
         }
         _Py_SetImmortal(bases);
     }
@@ -469,7 +469,7 @@ clear_tp_bases(PyTypeObject *self, int final)
                     Py_CLEAR(self->tp_bases);
                 }
                 else {
-                    assert(_Py_IsImmortal(self->tp_bases));
+                    assert(_Py_IsImmortalLoose(self->tp_bases));
                     _Py_ClearImmortal(self->tp_bases);
                 }
             }
@@ -534,7 +534,7 @@ clear_tp_mro(PyTypeObject *self, int final)
                     Py_CLEAR(self->tp_mro);
                 }
                 else {
-                    assert(_Py_IsImmortal(self->tp_mro));
+                    assert(_Py_IsImmortalLoose(self->tp_mro));
                     _Py_ClearImmortal(self->tp_mro);
                 }
             }
@@ -5657,7 +5657,7 @@ fini_static_type(PyInterpreterState *interp, PyTypeObject *type,
                  int isbuiltin, int final)
 {
     assert(type->tp_flags & _Py_TPFLAGS_STATIC_BUILTIN);
-    assert(_Py_IsImmortal((PyObject *)type));
+    assert(_Py_IsImmortalLoose((PyObject *)type));
 
     type_dealloc_common(type);
 
diff --git a/Python/bytecodes.c b/Python/bytecodes.c
index c222fcdb22f..d9533110af2 100644
--- a/Python/bytecodes.c
+++ b/Python/bytecodes.c
@@ -362,7 +362,7 @@ dummy_func(
             EXIT_IF(!PyLong_CheckExact(value));
             STAT_INC(TO_BOOL, hit);
             if (_PyLong_IsZero((PyLongObject *)value)) {
-                assert(_Py_IsImmortal(value));
+                assert(_Py_IsImmortalLoose(value));
                 res = Py_False;
             }
             else {
@@ -389,7 +389,7 @@ dummy_func(
             EXIT_IF(!PyUnicode_CheckExact(value));
             STAT_INC(TO_BOOL, hit);
             if (value == &_Py_STR(empty)) {
-                assert(_Py_IsImmortal(value));
+                assert(_Py_IsImmortalLoose(value));
                 res = Py_False;
             }
             else {
diff --git a/Python/executor_cases.c.h b/Python/executor_cases.c.h
index 7859269c772..799f3b7f692 100644
--- a/Python/executor_cases.c.h
+++ b/Python/executor_cases.c.h
@@ -347,7 +347,7 @@
             }
             STAT_INC(TO_BOOL, hit);
             if (_PyLong_IsZero((PyLongObject *)value)) {
-                assert(_Py_IsImmortal(value));
+                assert(_Py_IsImmortalLoose(value));
                 res = Py_False;
             }
             else {
@@ -398,7 +398,7 @@
             }
             STAT_INC(TO_BOOL, hit);
             if (value == &_Py_STR(empty)) {
-                assert(_Py_IsImmortal(value));
+                assert(_Py_IsImmortalLoose(value));
                 res = Py_False;
             }
             else {
diff --git a/Python/generated_cases.c.h b/Python/generated_cases.c.h
index dd334044d55..1488e4215cf 100644
--- a/Python/generated_cases.c.h
+++ b/Python/generated_cases.c.h
@@ -5939,7 +5939,7 @@
             DEOPT_IF(!PyLong_CheckExact(value), TO_BOOL);
             STAT_INC(TO_BOOL, hit);
             if (_PyLong_IsZero((PyLongObject *)value)) {
-                assert(_Py_IsImmortal(value));
+                assert(_Py_IsImmortalLoose(value));
                 res = Py_False;
             }
             else {
@@ -5999,7 +5999,7 @@
             DEOPT_IF(!PyUnicode_CheckExact(value), TO_BOOL);
             STAT_INC(TO_BOOL, hit);
             if (value == &_Py_STR(empty)) {
-                assert(_Py_IsImmortal(value));
+                assert(_Py_IsImmortalLoose(value));
                 res = Py_False;
             }
             else {