diff --git a/django/contrib/admin/utils.py b/django/contrib/admin/utils.py
index e604a2775030..3d5b023dea64 100644
--- a/django/contrib/admin/utils.py
+++ b/django/contrib/admin/utils.py
@@ -294,6 +294,7 @@ def lookup_field(name, obj, model_admin=None):
     except (FieldDoesNotExist, FieldIsAForeignKeyColumnName):
         # For non-regular field values, the value is either a method,
         # property, related field, or returned via a callable.
+        f = None
         if callable(name):
             attr = name
             value = attr(obj)
@@ -312,10 +313,12 @@ def lookup_field(name, obj, model_admin=None):
                         attr = getattr(attr, part, sentinel)
                         if attr is sentinel:
                             return None, None, None
+                    # The final field is needed for displaying boolean icons.
+                    if LOOKUP_SEP in name:
+                        f = get_fields_from_path(opts.model, name)[-1]
                 value = attr
             if hasattr(model_admin, "model") and hasattr(model_admin.model, name):
                 attr = getattr(model_admin.model, name)
-        f = None
     else:
         attr = None
         value = getattr(obj, name)
diff --git a/django/db/models/fields/__init__.py b/django/db/models/fields/__init__.py
index e0ad9f9a8cb0..e248b70ba37e 100644
--- a/django/db/models/fields/__init__.py
+++ b/django/db/models/fields/__init__.py
@@ -2821,7 +2821,7 @@ def get_prep_value(self, value):
     def get_db_prep_value(self, value, connection, prepared=False):
         if value is None:
             return None
-        if not isinstance(value, uuid.UUID):
+        if not prepared and not isinstance(value, uuid.UUID):
             value = self.to_python(value)
 
         if connection.features.has_native_uuid_field:
diff --git a/tests/admin_changelist/models.py b/tests/admin_changelist/models.py
index 0b594300d2a3..d5d0633122cc 100644
--- a/tests/admin_changelist/models.py
+++ b/tests/admin_changelist/models.py
@@ -17,6 +17,7 @@ class Child(models.Model):
     parent = models.ForeignKey(Parent, models.SET_NULL, editable=False, null=True)
     name = models.CharField(max_length=30, blank=True)
     age = models.IntegerField(null=True, blank=True)
+    is_active = models.BooleanField(default=True)
 
 
 class GrandChild(models.Model):
diff --git a/tests/admin_changelist/tests.py b/tests/admin_changelist/tests.py
index f0518494490d..ef0f8a0570ed 100644
--- a/tests/admin_changelist/tests.py
+++ b/tests/admin_changelist/tests.py
@@ -1768,6 +1768,35 @@ class ChildAdmin(admin.ModelAdmin):
         cl = m.get_changelist_instance(request)
         self.assertEqual(cl.get_ordering_field_columns(), {2: "asc"})
 
+    def test_list_display_related_field_boolean_display(self):
+        """
+        Related boolean fields (parent__is_active) display boolean icons.
+        """
+        parent = Parent.objects.create(name="Test Parent")
+        child_active = Child.objects.create(
+            name="Active Child", parent=parent, is_active=True
+        )
+        child_inactive = Child.objects.create(
+            name="Inactive Child", parent=parent, is_active=False
+        )
+
+        class GrandChildAdmin(admin.ModelAdmin):
+            list_display = ["name", "parent__is_active"]
+
+        GrandChild.objects.create(name="GrandChild of Active", parent=child_active)
+        GrandChild.objects.create(name="GrandChild of Inactive", parent=child_inactive)
+
+        m = GrandChildAdmin(GrandChild, custom_site)
+        request = self._mocked_authenticated_request("/grandchild/", self.superuser)
+        response = m.changelist_view(request)
+
+        # Boolean icons are rendered using img tags with specific alt text.
+        self.assertContains(response, 'alt="True"')
+        self.assertContains(response, 'alt="False"')
+        # Ensure "True" and "False" text are NOT in the response.
+        self.assertNotContains(response, ">True<")
+        self.assertNotContains(response, ">False<")
+
 
 class GetAdminLogTests(TestCase):
     def test_custom_user_pk_not_named_id(self):
diff --git a/tests/prefetch_related/models.py b/tests/prefetch_related/models.py
index de2d88395d1d..236ee57b2c9b 100644
--- a/tests/prefetch_related/models.py
+++ b/tests/prefetch_related/models.py
@@ -225,6 +225,10 @@ class CustomUUIDField(models.UUIDField):
         def get_prep_value(self, value):
             return str(value)
 
+        def get_db_prep_value(self, value, connection, prepared=False):
+            # Use prepared=False to ensure str -> UUID conversion is performed.
+            return super().get_db_prep_value(value, connection, prepared=False)
+
     id = CustomUUIDField(primary_key=True, default=uuid.uuid4)
     name = models.CharField(max_length=30)