From 7b11bf044ffb4b33548f2d013b29dc5b5c35e161 Mon Sep 17 00:00:00 2001
From: Phillip Davis <phdavis1027@gmail.com>
Date: Tue, 3 Mar 2026 15:34:18 -0500
Subject: [PATCH] test(webhook): failure sends one error

---
 test/property/test_webhook_handler.rb | 29 +++++++++++++++++++++++++++
 1 file changed, 29 insertions(+)

diff --git a/test/property/test_webhook_handler.rb b/test/property/test_webhook_handler.rb
index 44f91e1eb85c2c1cec51c97212f9487622b82296..3a30b203fb101030f5f0d5c3c65c42594b9408c2 100644
--- a/test/property/test_webhook_handler.rb
+++ b/test/property/test_webhook_handler.rb
@@ -72,4 +72,33 @@ class WebhookPropertyTest < Minitest::Test
 		}
 	end
 	em :test_multi_recipient_outbound_sends_no_receipts
+
+	def test_single_recipient_message_failed_sends_one_error
+		property_of {
+			Webhook
+				.new(REDIS)
+				.type { "message-failed" }
+				.message { |registered, jid, dir, top_level_to|
+					Message
+						.new(REDIS)
+						.to { [top_level_to] }
+						.generate(registered, jid, dir)
+				}
+				.generate
+		}.check { |metadata, example|
+			result = invoke_webhook(example)
+			assert_equal 200, result[0]
+			assert_equal(
+				written.length,
+				1,
+				"Message failed should only send one notification"
+			)
+			assert_kind_of(
+				::Blather::StanzaError,
+				written.shift,
+				"Should not notify message-failed"
+			)
+		}
+	end
+	em :test_single_recipient_message_failed_sends_one_error
 end