diff --git a/Lib/test/test_ctypes/test_pointers.py b/Lib/test/test_ctypes/test_pointers.py
index a8d243a45de0f4..792a3687dba93b 100644
--- a/Lib/test/test_ctypes/test_pointers.py
+++ b/Lib/test/test_ctypes/test_pointers.py
@@ -5,7 +5,7 @@
 import unittest
 from ctypes import (CDLL, CFUNCTYPE, Structure,
                     POINTER, pointer, _Pointer,
-                    byref, sizeof,
+                    addressof, byref, sizeof,
                     c_void_p, c_char_p,
                     c_byte, c_ubyte, c_short, c_ushort, c_int, c_uint,
                     c_long, c_ulong, c_longlong, c_ulonglong,
@@ -472,6 +472,105 @@ class C(Structure):
         ptr.set_type(c_int)
         self.assertIs(ptr._type_, c_int)
 
+    def test_pointer_lifecycle_basic(self):
+        i = c_long(1010)
+        p = pointer(i)
+        self.assertEqual(p[0], 1010)
+        self.assertIsNone(p._b_base_)
+        self.assertEqual(addressof(i), addressof(p.contents))
+
+    def test_pointer_lifecycle_set_contents(self):
+        i = c_long(2020)
+        p = pointer(c_long(1010))
+        p.contents = i
+        self.assertEqual(p[0], 2020)
+        self.assertIsNone(p._b_base_)
+        self.assertEqual(addressof(i), addressof(p.contents))
+
+    def test_pointer_lifecycle_set_pointer_contents(self):
+        i = c_long(3030)
+        p = pointer(c_long(1010))
+        pointer(p).contents.contents = i
+        self.assertEqual(p.contents.value, 3030)
+        self.assertEqual(addressof(i), addressof(p.contents))
+
+    def test_pointer_lifecycle_array_set_contents(self):
+        arr_type = POINTER(c_long) * 3
+        arr_obj = arr_type()
+        i = c_long(300300)
+        arr_obj[0] = pointer(c_long(100100))
+        arr_obj[1] = pointer(c_long(200200))
+        arr_obj[2] = pointer(i)
+        self.assertEqual(arr_obj[0].contents.value, 100100)
+        self.assertEqual(arr_obj[1].contents.value, 200200)
+        self.assertEqual(arr_obj[2].contents.value, 300300)
+        self.assertEqual(addressof(i), addressof(arr_obj[2].contents))
+
+    def test_pointer_lifecycle_array_set_pointer_contents(self):
+        arr_type = POINTER(c_long) * 3
+        arr_obj = arr_type()
+        i = c_long(200003)
+        arr_obj[0].contents = c_long(100001)
+        arr_obj[1].contents = c_long(200002)
+        arr_obj[2].contents = i
+        self.assertEqual(arr_obj[0].contents.value, 100001)
+        self.assertEqual(arr_obj[1].contents.value, 200002)
+        self.assertEqual(arr_obj[2].contents.value, 200003)
+        self.assertEqual(addressof(i), addressof(arr_obj[2].contents))
+
+    def test_pointer_lifecycle_array_set_pointer_contents_pointer(self):
+        arr_type = POINTER(c_long) * 3
+        arr_obj = arr_type()
+        i = c_long(200003)
+        pointer(arr_obj[0]).contents.contents = c_long(100001)
+        pointer(arr_obj[1]).contents.contents = c_long(200002)
+        pointer(arr_obj[2]).contents.contents = i
+        self.assertEqual(arr_obj[0].contents.value, 100001)
+        self.assertEqual(arr_obj[1].contents.value, 200002)
+        self.assertEqual(arr_obj[2].contents.value, 200003)
+        self.assertEqual(addressof(i), addressof(arr_obj[2].contents))
+
+    def test_pointer_lifecycle_struct_set_contents(self):
+        class S(Structure):
+            _fields_ = (("s", POINTER(c_long)),)
+        s = S(s=pointer(c_long(1111111)))
+        s.s.contents = c_long(2222222)
+        self.assertEqual(s.s.contents.value, 2222222)
+
+    def test_pointer_lifecycle_struct_set_contents_pointer(self):
+        class S(Structure):
+            _fields_ = (("s", POINTER(c_long)),)
+        s = S(s=pointer(c_long(1111111)))
+        pointer(s.s).contents.contents = c_long(2222222)
+        self.assertEqual(s.s.contents.value, 2222222)
+
+    def test_pointer_lifecycle_struct_set_pointer_contents(self):
+        class S(Structure):
+            _fields_ = (("s", POINTER(c_long)),)
+        s = S(s=pointer(c_long(1111111)))
+        s.s = pointer(c_long(3333333))
+        self.assertEqual(s.s.contents.value, 3333333)
+
+    def test_pointer_lifecycle_struct_with_extra_field(self):
+        class U(Structure):
+            _fields_ = (
+                ("s", POINTER(c_long)),
+                ("u", c_long),
+            )
+        u = U(s=pointer(c_long(1010101)))
+        u.s.contents = c_long(202020202)
+        self.assertEqual(u.s.contents.value, 202020202)
+
+    def test_pointer_lifecycle_struct_with_extra_field_pointer(self):
+        class U(Structure):
+            _fields_ = (
+                ("s", POINTER(c_uint)),
+                ("u", c_uint),
+            )
+        u = U(s=pointer(c_uint(1010101)))
+        pointer(u.s).contents.contents = c_uint(202020202)
+        self.assertEqual(u.s.contents.value, 202020202)
+
 
 if __name__ == '__main__':
     unittest.main()
diff --git a/Modules/_ctypes/_ctypes.c b/Modules/_ctypes/_ctypes.c
index 4bd3e380b3bc4b..6f46234c23a34b 100644
--- a/Modules/_ctypes/_ctypes.c
+++ b/Modules/_ctypes/_ctypes.c
@@ -2958,7 +2958,7 @@ KeepRef_lock_held(CDataObject *target, Py_ssize_t index, PyObject *keep)
     CDataObject *ob;
     PyObject *key;
 
-/* Optimization: no need to store None */
+    /* Optimization: no need to store None */
     if (keep == Py_None) {
         Py_DECREF(Py_None);
         return 0;
@@ -5724,8 +5724,34 @@ Pointer_set_contents_lock_held(PyObject *op, PyObject *value, void *closure)
        pointer instance has b_length set to 2 instead of 1, and we set
        'value' itself as the second item of the b_objects list, additionally.
     */
+
+    CDataObject * root = self->b_base;
+    /* perhaps, this is a bit excessive: if we have are in a chain of pointers
+     that starts with non-pointer (e.g. a union), can we consider the current
+     pointer to be "detached" from this chain? */
+    while (root != NULL && root->b_base != NULL) {
+        root = root->b_base;
+    }
+
+    /* If the b_base is NULL now or if we are a part of chain of pointers fully
+     modeled within ctypes, AND the value is a pointer, array, struct or union,
+     we just override the b_base. */
+    if ((root == NULL || PyType_IsSubtype(Py_TYPE(root), st->PyCPointer_Type)) &&
+        (PyType_IsSubtype(Py_TYPE(value), st->PyCPointer_Type) ||
+         PyType_IsSubtype(Py_TYPE(value), st->PyCArray_Type) ||
+         PyType_IsSubtype(Py_TYPE(value), st->Struct_Type) ||
+         PyType_IsSubtype(Py_TYPE(value), st->Union_Type))
+    ) {
+        Py_XSETREF(self->b_base, (CDataObject *) Py_NewRef(value));
+        return 0; // no need to add `value` to `keep` objects - it's in b_base
+    }
+
+    /* If we are a part of chain of pointers that is not fully modeled within
+     ctypes, (or modeled in a complex way, e.g., with arrays and structures),
+     then everything should be covered by keepref logic bellow */
+
     Py_INCREF(value);
-    if (-1 == KeepRef(self, 1, value))
+    if (-1 == KeepRef_lock_held(self, 1, value))
         return -1;
 
     keep = GetKeepedObjects(dst);
@@ -5733,7 +5759,7 @@ Pointer_set_contents_lock_held(PyObject *op, PyObject *value, void *closure)
         return -1;
 
     Py_INCREF(keep);
-    return KeepRef(self, 0, keep);
+    return KeepRef_lock_held(self, 0, keep);
 }
 
 static int