Surface channel delivery failures on agent replies instead of swallowing them

The previous fix made a broken SMTP/Telegram account non-fatal — the
reply gets recorded either way now — but that also made delivery
failures completely invisible: an agent sees their reply "sent"
successfully with no indication the customer never actually received it.
Added messages.deliveryFailed, set whenever the outbound send throws, and
a warning badge on the message bubble so this is now visible instead of
silent.

Co-Authored-By: Claude Sonnet 5 <noreply@anthropic.com>
Claude-Session: https://claude.ai/code/session_01Gh2UXUQUVBWroWEnn1FLFG

src/app/(admin)/tickets/[id]/ticket-thread.tsx

@@ -3,7 +3,7 @@
 import { useEffect, useRef, useState } from "react";
 import Link from "next/link";
 import { AnimatePresence, motion } from "framer-motion";
-import { ArrowLeft, Send, StickyNote, Paperclip, X, MessageSquareText } from "lucide-react";
+import { ArrowLeft, Send, StickyNote, Paperclip, X, MessageSquareText, TriangleAlert } from "lucide-react";
 import { useTicketEvents } from "@/lib/events/use-ticket-events";
 import { formatRelativeTime } from "@/lib/format";
 import { Avatar } from "@/components/avatar";
@@ -373,6 +373,15 @@ function MessageBubble({ message }: { message: MessageDTO }) {
         <p className={`text-[11px] ${isAgent ? "text-white/70" : "text-text-faint"}`}>
           {message.authorName} · {formatRelativeTime(message.createdAt)}
         </p>
+        {message.deliveryFailed && (
+          <p
+            className="mt-1 flex items-center gap-1 text-[11px] font-medium text-danger"
+            title="Сообщение сохранено, но не дошло до клиента — проверьте настройки почты/Telegram"
+          >
+            <TriangleAlert size={11} />
+            Не доставлено клиенту
+          </p>
+        )}
       </div>
     </motion.div>
   );

src/lib/db/migrations/0012_flawless_lord_tyger.sql

@@ -0,0 +1 @@
+ALTER TABLE `messages` ADD `delivery_failed` integer DEFAULT false NOT NULL;

src/lib/db/migrations/meta/_journal.json

@@ -85,6 +85,13 @@
       "when": 1788763637424,
       "tag": "0011_cute_boomer",
       "breakpoints": true
+    },
+    {
+      "idx": 12,
+      "version": "6",
+      "when": 1791361267938,
+      "tag": "0012_flawless_lord_tyger",
+      "breakpoints": true
     }
   ]
 }

src/lib/db/schema.ts

@@ -147,6 +147,11 @@ export const messages = sqliteTable("messages", {
   // email channel — lets a customer's future reply be matched back to the
   // exact ticket via In-Reply-To/References, even if they have other tickets.
   emailMessageId: text("email_message_id"),
+  // Set when this is an outbound agent reply whose channel delivery
+  // (email send / Telegram send) failed — the reply itself is always
+  // recorded regardless (see deliverAgentMessage), but the agent needs a
+  // way to tell "saved" from "the customer actually got this".
+  deliveryFailed: integer("delivery_failed", { mode: "boolean" }).notNull().default(false),
   createdAt: timestamps.createdAt,
 });
 

src/lib/tickets/delivery.ts

@@ -56,7 +56,13 @@ export async function deliverAgentMessage(params: {
   // shown in the thread) and the API route's catch-all turned it into a
   // misleading "Ticket not found". A broken mail/bot account should degrade
   // to "reply saved internally, not delivered" — never silent data loss.
+  // A ticket only ever has one channel, so at most one of the two branches
+  // below runs — this single flag is the outcome of whichever one does, and
+  // is what lets the agent tell "saved" from "the customer actually got
+  // this" in the UI (see messages.deliveryFailed).
   let emailMessageId: string | undefined;
+  let deliveryFailed = false;
+
   if (ticket.channel === "email") {
     const context = await getEmailThreadContext(params.ticketId);
     if (context) {
@@ -72,22 +78,12 @@ export async function deliverAgentMessage(params: {
         });
       } catch (err) {
         console.error(`Failed to send reply email for ticket ${params.ticketId}:`, err);
+        deliveryFailed = true;
       }
     }
-  }
-
-  const result = await recordAgentReply({
-    ticketId: params.ticketId,
-    agentId: params.agentId,
-    agentName: params.agentName,
-    body: params.body,
-    emailMessageId,
-    attachments: attachmentInput ? [attachmentInput] : undefined,
-  });
-
-  if (result.ticket.channel === "telegram") {
+  } else if (ticket.channel === "telegram") {
     const customer = await db.query.customers.findFirst({
-      where: eq(customers.id, result.ticket.customerId),
+      where: eq(customers.id, ticket.customerId),
     });
     if (customer?.telegramChatId) {
       try {
@@ -102,9 +98,20 @@ export async function deliverAgentMessage(params: {
         }
       } catch (err) {
         console.error(`Failed to deliver reply via Telegram for ticket ${params.ticketId}:`, err);
+        deliveryFailed = true;
       }
     }
   }
 
+  const result = await recordAgentReply({
+    ticketId: params.ticketId,
+    agentId: params.agentId,
+    agentName: params.agentName,
+    body: params.body,
+    emailMessageId,
+    deliveryFailed,
+    attachments: attachmentInput ? [attachmentInput] : undefined,
+  });
+
   return result;
 }

src/lib/tickets/service.ts

@@ -75,6 +75,7 @@ function toMessageDTO(message: typeof messages.$inferSelect, attachments: Attach
     visibility: message.visibility,
     attachments,
     createdAt: message.createdAt.getTime(),
+    deliveryFailed: message.deliveryFailed,
   };
 }
 
@@ -142,6 +143,7 @@ async function appendMessage(params: {
   direction: "in" | "out";
   visibility?: "public" | "internal";
   emailMessageId?: string;
+  deliveryFailed?: boolean;
   attachments?: AttachmentInput[];
 }) {
   const [message] = await db
@@ -155,6 +157,7 @@ async function appendMessage(params: {
       bodyHtml: params.bodyHtml ?? null,
       direction: params.direction,
       visibility: params.visibility ?? "public",
+      deliveryFailed: params.deliveryFailed ?? false,
       emailMessageId: params.emailMessageId,
     })
     .returning();
@@ -398,6 +401,7 @@ export async function recordAgentReply(params: {
   agentName: string;
   body: string;
   emailMessageId?: string;
+  deliveryFailed?: boolean;
   attachments?: AttachmentInput[];
 }) {
   const existing = await db.query.tickets.findFirst({ where: eq(tickets.id, params.ticketId) });
@@ -415,6 +419,7 @@ export async function recordAgentReply(params: {
     body: params.body,
     direction: "out",
     emailMessageId: params.emailMessageId,
+    deliveryFailed: params.deliveryFailed,
     attachments: params.attachments,
   });
 }

src/lib/tickets/types.ts

@@ -51,4 +51,5 @@ export interface MessageDTO {
   visibility: MessageVisibility;
   attachments: AttachmentDTO[];
   createdAt: number;
+  deliveryFailed: boolean;
 }