From f81cdf8768763a6bb33c6c5646614e4a4a9f1770 Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Marc-Andr=C3=A9=20Bombeck?= <mbombeck@gmail.com>
Date: Sun, 13 Sep 2026 14:50:33 +0200
Subject: [PATCH] fix(notifications): name TLS, protocol and envelope faults in
 email tests

A STARTTLS failure (port 465 set up as 587) and a protocol error now read as connection_failed, and an envelope or message refused without a reply code as upstream_rejected. They used to fall through to the 500 for an unnamed failure.

Refs #947
---
 .../senders/__tests__/email.test.ts           | 40 +++++++++++++++++++
 src/lib/notifications/senders/email.ts        | 11 ++++-
 2 files changed, 49 insertions(+), 2 deletions(-)

diff --git a/src/lib/notifications/senders/__tests__/email.test.ts b/src/lib/notifications/senders/__tests__/email.test.ts
index 83f12cec3..b785b1130 100644
--- a/src/lib/notifications/senders/__tests__/email.test.ts
+++ b/src/lib/notifications/senders/__tests__/email.test.ts
@@ -237,3 +237,43 @@ describe("sendViaEmail — the failure names itself for the test button", () =>
     expect(result.smtpCode).toBeUndefined();
   });
 });
+
+describe("sendViaEmail — transport and envelope faults are named too", () => {
+  it.each([
+    ["a TLS handshake failure", "ETLS", undefined, "connection_failed"],
+    ["a protocol error", "EPROTOCOL", undefined, "connection_failed"],
+    [
+      "an envelope refused without a code",
+      "EENVELOPE",
+      undefined,
+      "upstream_rejected",
+    ],
+    [
+      "a message refused without a code",
+      "EMESSAGE",
+      undefined,
+      "upstream_rejected",
+    ],
+    [
+      "an envelope refused with a temporary code",
+      "EENVELOPE",
+      451,
+      "upstream_error",
+    ],
+  ])("%s", async (_label, code, responseCode, failureCode) => {
+    loadEmailConfigMock.mockReturnValue(transport);
+    sendMailMock.mockRejectedValue(
+      Object.assign(new Error(String(code)), {
+        code,
+        ...(responseCode !== undefined ? { responseCode } : {}),
+      }),
+    );
+
+    const result = await sendViaEmail(
+      { recipient: "you@example.com" },
+      payload(),
+    );
+
+    expect(result.failureCode).toBe(failureCode);
+  });
+});
diff --git a/src/lib/notifications/senders/email.ts b/src/lib/notifications/senders/email.ts
index 2b518638d..22011e45e 100644
--- a/src/lib/notifications/senders/email.ts
+++ b/src/lib/notifications/senders/email.ts
@@ -106,13 +106,20 @@ function classifySmtpError(err: unknown): {
         : code === "ECONNECTION" ||
             code === "ESOCKET" ||
             code === "EDNS" ||
-            code === "ECONNREFUSED"
+            code === "ECONNREFUSED" ||
+            // STARTTLS or TLS handshake failure (typically port 465 set up
+            // as 587 or the reverse) and a server that does not speak SMTP.
+            code === "ETLS" ||
+            code === "EPROTOCOL"
           ? "connection_failed"
           : smtpCode !== undefined && smtpCode >= 500
             ? "upstream_rejected"
             : smtpCode !== undefined && smtpCode >= 400
               ? "upstream_error"
-              : undefined;
+              : // An envelope or message refused without a reply code.
+                code === "EENVELOPE" || code === "EMESSAGE"
+                ? "upstream_rejected"
+                : undefined;
   const extras = {
     ...(failureCode ? { failureCode } : {}),
     ...(smtpCode !== undefined ? { smtpCode } : {}),