diff --git a/test/property/test_webhook_handler.rb b/test/property/test_webhook_handler.rb
index cabce8badf6b99d63f847696a27e3809f4299727..68f6075697dc507519251ebecba0c24f1ece740c 100644
--- a/test/property/test_webhook_handler.rb
+++ b/test/property/test_webhook_handler.rb
@@ -471,4 +471,24 @@ class WebhookPropertyTest < Minitest::Test
 		}
 	end
 	em :test_message_with_non_array_to_returns_400
+
+	def test_message_with_empty_to_returns_400
+		property_of {
+			Webhook
+				.new(REDIS)
+				.message { |registered, jid, dir, top_level_to|
+					Message
+						.new(REDIS)
+						.to { [] }
+						.owner { top_level_to }
+						.generate(registered, jid, dir)
+				}
+				.generate
+		}.check { |metadata, example|
+			result = invoke_webhook(example)
+			assert_equal [400, {}, "Missing params\n"], result
+			assert_empty written
+		}
+	end
+	em :test_message_with_empty_to_returns_400
 end