diff --git a/Include/internal/pycore_ceval.h b/Include/internal/pycore_ceval.h
index a0fea389b6502c..c404fc6e67d193 100644
--- a/Include/internal/pycore_ceval.h
+++ b/Include/internal/pycore_ceval.h
@@ -350,9 +350,10 @@ _PyEval_SpecialMethodCanSuggest(PyObject *self, int oparg);
 #define _PY_EVAL_PLEASE_STOP_BIT (1U << 5)
 #define _PY_EVAL_EXPLICIT_MERGE_BIT (1U << 6)
 #define _PY_EVAL_JIT_INVALIDATE_COLD_BIT (1U << 7)
+#define _PY_EVAL_PROCESS_DELAYED_BIT (1U << 8)
 
 /* Reserve a few bits for future use */
-#define _PY_EVAL_EVENTS_BITS 8
+#define _PY_EVAL_EVENTS_BITS 9
 #define _PY_EVAL_EVENTS_MASK ((1 << _PY_EVAL_EVENTS_BITS)-1)
 
 static inline void
diff --git a/Lib/test/test_free_threading/test_qsbr.py b/Lib/test/test_free_threading/test_qsbr.py
new file mode 100644
index 00000000000000..8ce37b73e80a04
--- /dev/null
+++ b/Lib/test/test_free_threading/test_qsbr.py
@@ -0,0 +1,72 @@
+import threading
+import unittest
+
+from test.support import threading_helper
+
+
+class Holder:
+    pass
+
+
+def make_shared(func, *args):
+    t = threading.Thread(target=func, args=args)
+    t.start()
+    t.join()
+
+
+@threading_helper.requires_working_threading()
+class TestDelayedFreeReentrancy(unittest.TestCase):
+    ROUNDS = 1000
+
+    def queue_finalizers(self, callback):
+        class Finalizer:
+            def __del__(self):
+                callback()
+
+        holders = [Holder() for _ in range(self.ROUNDS)]
+        for h in holders:
+            h.__dict__ = {"f": Finalizer()}
+        return holders
+
+    def test_dict_resize(self):
+        d = {}
+        make_shared(d.get, 0)
+        holders = self.queue_finalizers(lambda: d.__setitem__(object(), 0))
+        for n, h in enumerate(holders):
+            h.__dict__ = {}
+            if n % 2:
+                h.__dict__ = {}
+            for k in list(d):
+                del d[k]
+            for i in range(6):
+                d[i] = i
+            self.assertEqual(len(d), len(list(d)))
+
+    def test_list_resize(self):
+        L = []
+        make_shared(L.append, 0)
+        holders = self.queue_finalizers(L.clear)
+        for n, h in enumerate(holders):
+            h.__dict__ = {}
+            if n % 2:
+                h.__dict__ = {}
+            L.clear()
+            for i in range(9):
+                L.insert(len(L), i)
+            self.assertEqual(len(L), len(list(L)))
+
+    def test_type_cache_invalidation(self):
+        class C:
+            x = None
+
+        holders = self.queue_finalizers(lambda: C.x)
+        for h in holders:
+            h.__dict__ = {}
+            C.x
+            new = object()
+            C.x = new
+            self.assertIs(C.x, new)
+
+
+if __name__ == "__main__":
+    unittest.main()
diff --git a/Misc/NEWS.d/next/Core_and_Builtins/2026-10-26-10-18-26.gh-issue-160697.qSbR1f.rst b/Misc/NEWS.d/next/Core_and_Builtins/2026-10-26-10-18-26.gh-issue-160697.qSbR1f.rst
new file mode 100644
index 00000000000000..55649732e8f4b2
--- /dev/null
+++ b/Misc/NEWS.d/next/Core_and_Builtins/2026-10-26-10-18-26.gh-issue-160697.qSbR1f.rst
@@ -0,0 +1,4 @@
+Fix crashes and hangs in the :term:`free-threaded build` when a destructor
+ran in the middle of a :class:`dict` resize, a :class:`list` resize or a type
+cache update. The thread's queue of delayed frees is now processed only from
+the eval breaker, instead of synchronously when the queue fills up.
diff --git a/Objects/obmalloc.c b/Objects/obmalloc.c
index 3ad485620ede41..0f3436cd4eb0fb 100644
--- a/Objects/obmalloc.c
+++ b/Objects/obmalloc.c
@@ -1,6 +1,7 @@
 /* Python's malloc wrappers (see pymem.h) */
 
 #include "Python.h"
+#include "pycore_ceval.h"
 #include "pycore_interp.h"        // _PyInterpreterState_HasFeature
 #include "pycore_mmap.h"          // _PyAnnotateMemoryMap()
 #include "pycore_object.h"        // _PyDebugAllocatorStats() definition
@@ -1513,10 +1514,8 @@ free_delayed(uintptr_t ptr, size_t size)
     buf->wr_idx++;
 
     if (buf->wr_idx == WORK_ITEMS_PER_CHUNK) {
-        // Normally the processing of delayed items is done from the eval
-        // breaker.  Processing here is a safety measure to ensure too much
-        // work does not accumulate.
-        _PyMem_ProcessDelayed((PyThreadState *)tstate);
+        _Py_set_eval_breaker_bit((PyThreadState *)tstate,
+                                 _PY_EVAL_PROCESS_DELAYED_BIT);
     }
 #endif
 }
@@ -1626,6 +1625,7 @@ _PyMem_ProcessDelayed(PyThreadState *tstate)
     _PyThreadStateImpl *tstate_impl = (_PyThreadStateImpl *)tstate;
 
     tstate_impl->qsbr->should_process = false;
+    _Py_unset_eval_breaker_bit(tstate, _PY_EVAL_PROCESS_DELAYED_BIT);
 
     // Process thread-local work
     process_queue(&tstate_impl->mem_free_queue, tstate_impl, true, NULL, NULL);
diff --git a/Python/ceval_gil.c b/Python/ceval_gil.c
index 49b2ede4ed3e60..bc86164f5ceab8 100644
--- a/Python/ceval_gil.c
+++ b/Python/ceval_gil.c
@@ -1389,7 +1389,9 @@ _Py_HandlePending(PyThreadState *tstate)
         _Py_brc_merge_refcounts(tstate);
     }
     /* Process deferred memory frees held by QSBR */
-    if (_Py_qsbr_should_process(((_PyThreadStateImpl *)tstate)->qsbr)) {
+    if ((breaker & _PY_EVAL_PROCESS_DELAYED_BIT) != 0 ||
+        _Py_qsbr_should_process(((_PyThreadStateImpl *)tstate)->qsbr))
+    {
         _PyMem_ProcessDelayed(tstate);
     }
 #endif