diff --git a/tests/Unit/LicenseTest.php b/tests/Unit/LicenseTest.php
index df50839812..58b6003814 100644
--- a/tests/Unit/LicenseTest.php
+++ b/tests/Unit/LicenseTest.php
@@ -192,6 +192,76 @@ class LicenseTest extends TestCase
         $this->assertFalse($l->isValid());
     }
 
+
+    public function testPopDocs()
+    {
+
+        $docs = [
+            '8f47aa3c-9c51-4f4a-b45d-c275945d6284',
+            '2e6d7168-43b9-4f92-9c3a-b8d6f3e9c5a1',
+            'f9c12d4b-6e8a-4d7f-b3c5-a2e9f8d1b7c4',
+            '7a3b5c9d-2e4f-4a6b-8c1d-9e7f5a3b2d4c',
+            '1d9e8f7c-6b5a-4c3d-2e1f-9a8b7c6d5e4f',
+            '4b8c2d6e-9f5a-3d7b-1c4e-8a2b9d7c6f5e',
+            '3e2d1c9b-8a7f-6d5e-4c3b-2d1e9f8a7b6c',
+            '5f4e3d2c-1b9a-8c7d-6e5f-4d3c2b1a9e8d',
+            '9d8c7b6a-5e4f-3d2c-1b9a-8c7d6e5f4d3c',
+            '6c5d4e3f-2b1a-9d8c-7e6f-5d4c3b2a1e9d',
+        ];
+
+        $processed_docs = [
+            '8f47aa3c-9c51-4f4a-b45d-c275945d6284', 
+            '2e6d7168-43b9-4f92-9c3a-b8d6f3e9c5a1',
+            'f9c12d4b-6e8a-4d7f-b3c5-a2e9f8d1b7c4',
+            '7a3b5c9d-2e4f-4a6b-8c1d-9e7f5a3b2d4c',
+            '1d9e8f7c-6b5a-4c3d-2e1f-9a8b7c6d5e4f',
+            '4b8c2d6e-9f5a-3d7b-1c4e-8a2b9d7c6f5e',
+            '3e2d1c9b-8a7f-6d5e-4c3b-2d1e9f8a7b6c',
+            '5f4e3d2c-1b9a-8c7d-6e5f-4d3c2b1a9e8d',
+            '9d8c7b6a-5e4f-3d2c-1b9a-8c7d6e5f4d3c',
+        ];
+
+        $tes = [
+            [
+                'legal_entity_id' => rand(1, 100),
+                'company_key' => \Illuminate\Support\Str::random(32),
+                'received_documents' => []
+            ],
+            [
+                'legal_entity_id' => rand(1, 100),
+                'company_key' => \Illuminate\Support\Str::random(32),
+                'received_documents' => []
+            ],
+            [
+                'legal_entity_id' => 50,
+                'company_key' => 'abcd',
+                'received_documents' => $docs
+            ]
+        ];
+
+        $l = $this->stubLicense($tes);
+
+        $tax_entity = $l->findEntity('legal_entity_id', 50);
+
+        $this->assertNotNull($tax_entity);
+        $this->assertEquals(50, $tax_entity->legal_entity_id);
+        $this->assertCount(10, $tax_entity->received_documents);
+
+        $tax_entity->received_documents = array_values(
+            array_diff($tax_entity->received_documents, $processed_docs)
+        );
+
+        $l->updateEntity($tax_entity);
+        $l->refresh();
+
+        $tax_entity = $l->findEntity('legal_entity_id', 50);
+
+        $this->assertEquals(50, $tax_entity->legal_entity_id);
+        $this->assertCount(1, $tax_entity->received_documents);
+
+        $this->assertEquals('6c5d4e3f-2b1a-9d8c-7e6f-5d4c3b2a1e9d', $tax_entity->received_documents[0]);
+    
+    }
    
 
 }