diff --git a/django/db/models/query.py b/django/db/models/query.py
index 40f7ae6ea94..4085e618cf4 100644
--- a/django/db/models/query.py
+++ b/django/db/models/query.py
@@ -632,6 +632,8 @@ class QuerySet(object):
         self._for_write = True
         query = self.query.clone(sql.UpdateQuery)
         query.add_update_values(kwargs)
+        # Clear any annotations so that they won't be present in subqueries.
+        query._annotations = None
         with transaction.atomic(using=self.db, savepoint=False):
             rows = query.get_compiler(self.db).execute_sql(CURSOR)
         self._result_cache = None
diff --git a/django/db/models/sql/subqueries.py b/django/db/models/sql/subqueries.py
index 316a5c684d6..fc9683064f2 100644
--- a/django/db/models/sql/subqueries.py
+++ b/django/db/models/sql/subqueries.py
@@ -142,7 +142,11 @@ class UpdateQuery(Query):
         that will be used to generate the UPDATE query. Might be more usefully
         called add_update_targets() to hint at the extra information here.
         """
-        self.values.extend(values_seq)
+        for field, model, val in values_seq:
+            if hasattr(val, 'resolve_expression'):
+                # Resolve expressions here so that annotations are no longer needed
+                val = val.resolve_expression(self, allow_joins=False, for_save=True)
+            self.values.append((field, model, val))
 
     def add_related_update(self, model, field, value):
         """
diff --git a/tests/update/tests.py b/tests/update/tests.py
index 3dc97c9173a..89593f8dfc6 100644
--- a/tests/update/tests.py
+++ b/tests/update/tests.py
@@ -1,7 +1,7 @@
 from __future__ import unicode_literals
 
 from django.core.exceptions import FieldError
-from django.db.models import F, Max
+from django.db.models import Count, F, Max
 from django.test import TestCase
 
 from .models import A, B, Bar, D, DataPoint, Foo, RelatedPoint
@@ -158,3 +158,23 @@ class AdvancedTests(TestCase):
         qs = DataPoint.objects.annotate(max=Max('value'))
         with self.assertRaisesMessage(FieldError, 'Aggregate functions are not allowed in this query'):
             qs.update(another_value=F('max'))
+
+    def test_update_annotated_multi_table_queryset(self):
+        """
+        Update of a queryset that's been annotated and involves multiple tables.
+        """
+        # Trivial annotated update
+        qs = DataPoint.objects.annotate(related_count=Count('relatedpoint'))
+        self.assertEqual(qs.update(value='Foo'), 3)
+        # Update where annotation is used for filtering
+        qs = DataPoint.objects.annotate(related_count=Count('relatedpoint'))
+        self.assertEqual(qs.filter(related_count=1).update(value='Foo'), 1)
+        # Update where annotation is used in update parameters
+        # #26539 - This isn't forbidden but also doesn't generate proper SQL
+        # qs = RelatedPoint.objects.annotate(data_name=F('data__name'))
+        # updated = qs.update(name=F('data_name'))
+        # self.assertEqual(updated, 1)
+        # Update where aggregation annotation is used in update parameters
+        qs = RelatedPoint.objects.annotate(max=Max('data__value'))
+        with self.assertRaisesMessage(FieldError, 'Aggregate functions are not allowed in this query'):
+            qs.update(name=F('max'))