diff --git a/core/lib/Drupal/Core/Plugin/Context/ContextDefinition.php b/core/lib/Drupal/Core/Plugin/Context/ContextDefinition.php
index 895650c89ca..c2e5d53331f 100644
--- a/core/lib/Drupal/Core/Plugin/Context/ContextDefinition.php
+++ b/core/lib/Drupal/Core/Plugin/Context/ContextDefinition.php
@@ -4,6 +4,7 @@ namespace Drupal\Core\Plugin\Context;
 
 use Drupal\Core\DependencyInjection\DependencySerializationTrait;
 use Drupal\Core\TypedData\TypedDataTrait;
+use Symfony\Component\Validator\ConstraintViolationList;
 
 /**
  * Defines a class for context definitions.
@@ -307,7 +308,15 @@ class ContextDefinition implements ContextDefinitionInterface {
     $validator = $this->getTypedDataManager()->getValidator();
     foreach ($values as $value) {
       $constraints = array_values($this->getConstraintObjects());
-      $violations = $validator->validate($value, $constraints);
+      if ($definition->isMultiple()) {
+        $violations = new ConstraintViolationList();
+        foreach ($value as $item) {
+          $violations->addAll($validator->validate($item, $constraints));
+        }
+      }
+      else {
+        $violations = $validator->validate($value, $constraints);
+      }
       foreach ($violations as $delta => $violation) {
         // Remove any violation that does not correspond to the constraints.
         if (!in_array($violation->getConstraint(), $constraints)) {
diff --git a/core/tests/Drupal/KernelTests/Core/Plugin/ContextDefinitionTest.php b/core/tests/Drupal/KernelTests/Core/Plugin/ContextDefinitionTest.php
index bb9fd968ca2..e332be68df6 100644
--- a/core/tests/Drupal/KernelTests/Core/Plugin/ContextDefinitionTest.php
+++ b/core/tests/Drupal/KernelTests/Core/Plugin/ContextDefinitionTest.php
@@ -2,6 +2,7 @@
 
 namespace Drupal\KernelTests\Core\Plugin;
 
+use Drupal\Core\Plugin\Context\Context;
 use Drupal\Core\Plugin\Context\ContextDefinition;
 use Drupal\Core\Plugin\Context\EntityContext;
 use Drupal\Core\Plugin\Context\EntityContextDefinition;
@@ -33,6 +34,16 @@ class ContextDefinitionTest extends KernelTestBase {
     $requirement = new ContextDefinition('any');
     $context = EntityContext::fromEntity($value);
     $this->assertTrue($requirement->isSatisfiedBy($context));
+
+    // Test with multiple values.
+    $definition = EntityContextDefinition::create('entity_test');
+    $definition->setMultiple();
+    $entities = [
+      EntityTest::create([]),
+      EntityTest::create([]),
+    ];
+    $context = new Context($definition, $entities);
+    $this->assertTrue($definition->isSatisfiedBy($context));
   }
 
   /**