diff --git a/Include/internal/pycore_ceval.h b/Include/internal/pycore_ceval.h
index a0fea389b6502c0..f5482480a5f76cc 100644
--- a/Include/internal/pycore_ceval.h
+++ b/Include/internal/pycore_ceval.h
@@ -314,7 +314,7 @@ PyObject * _PyEval_ImportNameWithImport(
     PyObject *locals, PyObject *name, PyObject *fromlist, PyObject *level);
 PyAPI_FUNC(PyObject *)_PyEval_MatchClass(PyThreadState *tstate, PyObject *subject, PyObject *type, Py_ssize_t nargs, PyObject *kwargs);
 PyAPI_FUNC(PyObject *)_PyEval_MatchKeys(PyThreadState *tstate, PyObject *map, PyObject *keys);
-PyAPI_FUNC(void) _PyEval_MonitorRaise(PyThreadState *tstate, _PyInterpreterFrame *frame, _Py_CODEUNIT *instr);
+PyAPI_FUNC(int) _PyEval_MonitorRaise(PyThreadState *tstate, _PyInterpreterFrame *frame, _Py_CODEUNIT *instr);
 PyAPI_FUNC(bool) _PyEval_NoToolsForUnwind(PyThreadState *tstate, _PyInterpreterFrame *frame);
 PyAPI_FUNC(int) _PyEval_UnpackIterableStackRef(PyThreadState *tstate, PyObject *v, int argcnt, int argcntafter, _PyStackRef *sp);
 PyAPI_FUNC(void) _PyEval_FrameClearAndPop(PyThreadState *tstate, _PyInterpreterFrame *frame);
diff --git a/Lib/test/test_monitoring.py b/Lib/test/test_monitoring.py
index 24cc51f4b4053ab..765ebb6b523feae 100644
--- a/Lib/test/test_monitoring.py
+++ b/Lib/test/test_monitoring.py
@@ -895,6 +895,31 @@ def implicit_stop_iteration(iterator=None):
         # This will record a STOP_ITERATION event for the StopIteration.
         self.check_events(implicit_stop_iteration, expected, recorders=recorders)
 
+    def test_raise_callback_stop_iteration_in_for(self):
+        class Empty:
+            def __iter__(self):
+                return self
+
+            def __next__(self):
+                raise StopIteration
+
+        def run():
+            for _ in Empty():
+                pass
+
+        def on_raise(code, offset, exc):
+            if code is run.__code__ and isinstance(exc, StopIteration):
+                raise RuntimeError("monitor callback failed")
+
+        try:
+            sys.monitoring.register_callback(TEST_TOOL, E.RAISE, on_raise)
+            sys.monitoring.set_events(TEST_TOOL, E.RAISE)
+            with self.assertRaisesRegex(RuntimeError, "monitor callback failed"):
+                run()
+        finally:
+            sys.monitoring.set_events(TEST_TOOL, 0)
+            sys.monitoring.register_callback(TEST_TOOL, E.RAISE, None)
+
     initial = [
         ("raise", ZeroDivisionError),
         ("handled", ZeroDivisionError)
@@ -2652,6 +2677,73 @@ def test_func(x):
 
 class TestTier2Optimizer(CheckEvents):
 
+    @requires_specialization
+    def test_raise_callback_stop_iteration_in_for_tier2(self):
+        _testinternalcapi = import_helper.import_module("_testinternalcapi")
+        _opcode = import_helper.import_module("_opcode")
+        threshold = _testinternalcapi.SPECIALIZATION_THRESHOLD
+        monitoring_enabled = False
+
+        class Iterator:
+            def __init__(self):
+                self.count = 0
+
+            def __iter__(self):
+                return self
+
+            def __next__(self):
+                if self.count < threshold:
+                    self.count += 1
+                    return self.count
+                if monitoring_enabled:
+                    sys.monitoring.set_events(TEST_TOOL, E.RAISE)
+                raise StopIteration
+
+        def run():
+            for _ in Iterator():
+                pass
+
+        # Warm up the loop before enabling monitoring to create the executor.
+        run()
+        code = run.__code__
+        executor_offset = None
+        executor = None
+        for offset in range(0, len(code.co_code), 2):
+            try:
+                candidate = _opcode.get_executor(code, offset)
+            except ValueError:
+                continue
+            except RuntimeError as exc:
+                if "Executors are not available in this build" not in str(exc):
+                    raise
+                self.skipTest("requires tier-2 executor support")
+            if candidate is not None:
+                uops = [op[0] for op in candidate]
+                if "_ITER_NEXT_INLINE" in uops:
+                    executor_offset = offset
+                    executor = candidate
+                    break
+        if executor is None:
+            self.skipTest("requires _ITER_NEXT_INLINE executor")
+
+        callback_offset = None
+
+        def on_raise(code, offset, exc):
+            nonlocal callback_offset
+            if code is run.__code__ and isinstance(exc, StopIteration):
+                callback_offset = offset
+                raise RuntimeError("monitor callback failed")
+
+        monitoring_enabled = True
+        try:
+            sys.monitoring.register_callback(TEST_TOOL, E.RAISE, on_raise)
+            with self.assertRaisesRegex(RuntimeError, "monitor callback failed"):
+                run()
+            self.assertEqual(callback_offset, executor_offset)
+        finally:
+            sys.monitoring.set_events(TEST_TOOL, 0)
+            sys.monitoring.register_callback(TEST_TOOL, E.RAISE, None)
+
     def test_monitoring_already_opimized_loop(self):
         _testinternalcapi = import_helper.import_module("_testinternalcapi")
 
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-10-26-18-00-00.gh-issue-160676.AdhN7x.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-10-26-18-00-00.gh-issue-160676.AdhN7x.rst
new file mode 100644
index 000000000000000..3564d77709bad4d
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2026-10-26-18-00-00.gh-issue-160676.AdhN7x.rst
@@ -0,0 +1,2 @@
+Fix an issue where exceptions raised by a ``sys.monitoring`` callback for
+``StopIteration`` could be swallowed by a ``for`` loop.
diff --git a/Python/bytecodes.c b/Python/bytecodes.c
index 42ad83daa1ea461..3650092ddb62a77 100644
--- a/Python/bytecodes.c
+++ b/Python/bytecodes.c
@@ -3818,7 +3818,10 @@ dummy_func(
             if (item == NULL) {
                 if (_PyErr_Occurred(tstate)) {
                     if (_PyErr_ExceptionMatches(tstate, PyExc_StopIteration)) {
-                        _PyEval_MonitorRaise(tstate, frame, frame->instr_ptr);
+                        int err = _PyEval_MonitorRaise(tstate, frame, frame->instr_ptr);
+                        if (err < 0) {
+                            ERROR_NO_POP();
+                        }
                         _PyErr_Clear(tstate);
                     }
                     else {
diff --git a/Python/ceval.c b/Python/ceval.c
index 223106065c603c4..700b13444cdd767 100644
--- a/Python/ceval.c
+++ b/Python/ceval.c
@@ -2542,14 +2542,14 @@ _PyEval_UnpackIterableStackRef(PyThreadState *tstate, PyObject *v,
 
 
 
-void
+int
 _PyEval_MonitorRaise(PyThreadState *tstate, _PyInterpreterFrame *frame,
               _Py_CODEUNIT *instr)
 {
     if (no_tools_for_local_event(tstate, frame, PY_MONITORING_EVENT_RAISE)) {
-        return;
+        return 0;
     }
-    do_monitor_exc(tstate, frame, instr, PY_MONITORING_EVENT_RAISE);
+    return do_monitor_exc(tstate, frame, instr, PY_MONITORING_EVENT_RAISE);
 }
 
 bool
@@ -3834,7 +3834,10 @@ _PyStackRef _PyForIter_VirtualIteratorNext(PyThreadState* tstate, _PyInterpreter
     if (next == NULL) {
         if (_PyErr_Occurred(tstate)) {
             if (_PyErr_ExceptionMatches(tstate, PyExc_StopIteration)) {
-                _PyEval_MonitorRaise(tstate, frame, frame->instr_ptr);
+                int err = _PyEval_MonitorRaise(tstate, frame, frame->instr_ptr);
+                if (err < 0) {
+                    return PyStackRef_ERROR;
+                }
                 _PyErr_Clear(tstate);
             }
             else {
diff --git a/Python/executor_cases.c.h b/Python/executor_cases.c.h
index bc85ccd9ddb4fc1..3a5e91c68c48969 100644
--- a/Python/executor_cases.c.h
+++ b/Python/executor_cases.c.h
@@ -15032,8 +15032,12 @@
                     if (_PyErr_ExceptionMatches(tstate, PyExc_StopIteration)) {
                         assert(stack_pointer == _PyFrame_GetStackPointer(frame));
                         _PyFrame_StackPointerValidate(frame);
-                        _PyEval_MonitorRaise(tstate, frame, frame->instr_ptr);
+                        int err = _PyEval_MonitorRaise(tstate, frame, frame->instr_ptr);
                         _PyFrame_StackPointerInvalidate(frame);
+                        if (err < 0) {
+                            SET_CURRENT_CACHED_VALUES(0);
+                            JUMP_TO_ERROR();
+                        }
                         assert(stack_pointer == _PyFrame_GetStackPointer(frame));
                         _PyFrame_StackPointerValidate(frame);
                         _PyErr_Clear(tstate);