diff --git a/backend/src/openarchiefbeheer/destruction/tests/test_utils.py b/backend/src/openarchiefbeheer/destruction/tests/test_utils.py
index 0c730033..13442f01 100644
--- a/backend/src/openarchiefbeheer/destruction/tests/test_utils.py
+++ b/backend/src/openarchiefbeheer/destruction/tests/test_utils.py
@@ -1,9 +1,13 @@
+from django.core.exceptions import ObjectDoesNotExist
 from django.test import TestCase
 
+from timeline_logger.models import TimelineLog
+
 from openarchiefbeheer.accounts.tests.factories import UserFactory
 from openarchiefbeheer.zaken.tests.factories import ZaakFactory
 
 from ..constants import ListRole
+from ..models import DestructionListItem
 from ..utils import process_new_reviewer, resync_items_and_zaken
 from .factories import (
     DestructionListAssigneeFactory,
@@ -48,12 +52,20 @@ def test_resync_zaken_missing(self):
         ZaakFactory.create(url="http://zaken.nl/2")
         item1 = DestructionListItemFactory.create(_zaak_url="http://zaken.nl/1")
         item2 = DestructionListItemFactory.create(_zaak_url="http://zaken.nl/3")
+        item2_pk = item2.pk
+        destruction_list2 = item2.destruction_list
 
         resync_items_and_zaken()
 
         item1.refresh_from_db()
-        item2.refresh_from_db()
 
         self.assertIsNotNone(item1.zaak)
         self.assertEqual(item1.zaak.url, "http://zaken.nl/1")
-        self.assertIsNone(item2.zaak)
+        with self.assertRaises(ObjectDoesNotExist):
+            DestructionListItem.objects.get(pk=item2_pk)
+
+        logs = TimelineLog.objects.for_object(destruction_list2)
+
+        self.assertEqual(logs.count(), 1)
+        self.assertEqual(logs[0].extra_data["number_deleted_items"], 1)
+        self.assertEqual(logs[0].extra_data["number_of_zaken"], 0)
diff --git a/backend/src/openarchiefbeheer/destruction/utils.py b/backend/src/openarchiefbeheer/destruction/utils.py
index c97f74e1..bdcb5d08 100644
--- a/backend/src/openarchiefbeheer/destruction/utils.py
+++ b/backend/src/openarchiefbeheer/destruction/utils.py
@@ -16,6 +16,7 @@
 from openarchiefbeheer.config.models import ArchiveConfig
 from openarchiefbeheer.emails.models import EmailConfig
 from openarchiefbeheer.emails.render_backend import get_sandboxed_backend
+from openarchiefbeheer.logging import logevent
 from openarchiefbeheer.selection.models import SelectionItem
 from openarchiefbeheer.utils.results_store import ResultStore
 from openarchiefbeheer.zaken.models import Zaak
@@ -137,12 +138,30 @@ def process_new_reviewer(
 
 
 def resync_items_and_zaken() -> None:
+    # Using the _zaak_url field, link the item to the zaak again
     DestructionListItem.objects.filter(~Q(_zaak_url=""), zaak__isnull=True).update(
         zaak_id=Subquery(
             Zaak.objects.filter(url=OuterRef("_zaak_url")).values("pk")[:1]
         )
     )
 
+    # If the cases could not be linked again, the zaak does not exist anymore.
+    # We need to delete them and log the deletion from the destruction list
+    orphan_items = DestructionListItem.objects.filter(
+        ~Q(_zaak_url=""), zaak__isnull=True
+    )
+    destruction_lists = DestructionList.objects.filter(
+        pk__in=orphan_items.distinct("destruction_list").values_list(
+            "destruction_list", flat=True
+        )
+    )
+    for destruction_list in destruction_lists:
+        items_in_list = orphan_items.filter(destruction_list=destruction_list)
+
+        number_deleted_items, _ = items_in_list.delete()
+
+        logevent.destruction_list_items_deleted(destruction_list, number_deleted_items)
+
 
 def create_zaak_for_report(
     destruction_list: DestructionList, store: ResultStore
diff --git a/backend/src/openarchiefbeheer/logging/logevent.py b/backend/src/openarchiefbeheer/logging/logevent.py
index f952af94..d09e1d16 100644
--- a/backend/src/openarchiefbeheer/logging/logevent.py
+++ b/backend/src/openarchiefbeheer/logging/logevent.py
@@ -252,6 +252,21 @@ def destruction_list_deletion_triggered(
     )
 
 
+def destruction_list_items_deleted(
+    destruction_list: DestructionList, number_deleted_items: int
+) -> None:
+    _create_log(
+        model=destruction_list,
+        event="destruction_list_items_deleted",
+        extra_data={
+            "number_deleted_items": number_deleted_items,
+            "number_of_zaken": destruction_list.items.filter(
+                status=ListItemStatus.suggested
+            ).count(),
+        },
+    )
+
+
 def resync_started() -> None:
     return TimelineLog.objects.create(
         template="logging/resync_started.txt",
diff --git a/backend/src/openarchiefbeheer/logging/templates/logging/destruction_list_items_deleted.txt b/backend/src/openarchiefbeheer/logging/templates/logging/destruction_list_items_deleted.txt
new file mode 100644
index 00000000..17fa137c
--- /dev/null
+++ b/backend/src/openarchiefbeheer/logging/templates/logging/destruction_list_items_deleted.txt
@@ -0,0 +1,9 @@
+{% load i18n %}{% blocktranslate trimmed with list_name=log.content_object.name %}
+List "{{ list_name }}" has been updated after resyncing the cases with Open Zaak.
+{% endblocktranslate %}
+{% blocktranslate trimmed with number_deleted_items=log.extra_data.number_deleted_items count counter=log.extra_data.number_deleted_items %}
+One item was deleted.{% plural %}{{ number_deleted_items }} items were deleted.
+{% endblocktranslate %}
+{% blocktranslate trimmed with number_of_zaken=log.extra_data.number_of_zaken count counter=log.extra_data.number_of_zaken %}
+There is now one zaak on the list.{% plural %}There are now {{ number_of_zaken }} zaken on the list.
+{% endblocktranslate %}