Message attachment order

apps/web/app/(ee)/api/cron/messages/notify-partner/route.ts

@@ -1,6 +1,7 @@
 import { createId } from "@/lib/api/create-id";
 import { handleAndReturnErrorResponse } from "@/lib/api/errors";
 import { verifyQstashSignature } from "@/lib/cron/verify-qstash";
+import { messageAttachmentsOrderBy } from "@/lib/messages/utils";
 import { prisma } from "@/lib/prisma";
 import { sendBatchEmail } from "@dub/email";
 import NewMessageFromProgram from "@dub/email/templates/new-message-from-program";
@@ -55,6 +56,7 @@ export async function POST(req: Request) {
             include: {
               senderUser: true,
               attachments: {
+                orderBy: messageAttachmentsOrderBy,
                 select: {
                   name: true,
                   size: true,

apps/web/app/(ee)/api/cron/messages/notify-program/route.ts

@@ -1,6 +1,7 @@
 import { createId } from "@/lib/api/create-id";
 import { handleAndReturnErrorResponse } from "@/lib/api/errors";
 import { verifyQstashSignature } from "@/lib/cron/verify-qstash";
+import { messageAttachmentsOrderBy } from "@/lib/messages/utils";
 import { prisma } from "@/lib/prisma";
 import { sendBatchEmail } from "@dub/email";
 import NewMessageFromPartner from "@dub/email/templates/new-message-from-partner";
@@ -57,6 +58,7 @@ export async function POST(req: Request) {
             include: {
               senderPartner: true,
               attachments: {
+                orderBy: messageAttachmentsOrderBy,
                 select: {
                   name: true,
                   size: true,

apps/web/app/(ee)/api/intercom/webhook/process/conversation-admin-replied.ts

@@ -10,7 +10,10 @@ import {
   intercomCredentialsSchema,
 } from "@/lib/integrations/intercom/schema";
 import { PROGRAM_ALLOWED_ATTACHMENT_TYPES } from "@/lib/messages/constants";
-import { sanitizeFileName } from "@/lib/messages/utils";
+import {
+  mapMessageAttachmentsForCreate,
+  sanitizeFileName,
+} from "@/lib/messages/utils";
 import { prisma } from "@/lib/prisma";
 import { storage } from "@/lib/storage";
 import {
@@ -112,13 +115,7 @@ export async function handleConversationAdminReplied({
           text: originalMessage,
           ...(storedAttachments.length > 0 && {
             attachments: {
-              create: storedAttachments.map((attachment) => ({
-                id: createId({ prefix: "msa_" }),
-                storageKey: attachment.storageKey,
-                name: attachment.name,
-                size: attachment.size,
-                type: attachment.type,
-              })),
+              create: mapMessageAttachmentsForCreate(storedAttachments),
             },
           }),
         },

apps/web/app/(ee)/api/messages/route.ts

@@ -6,6 +6,7 @@ import {
   PartnerMessagesSchema,
   getPartnerMessagesQuerySchema,
 } from "@/lib/messages/schemas";
+import { messageAttachmentsOrderBy } from "@/lib/messages/utils";
 import { prisma } from "@/lib/prisma";
 import { NextResponse } from "next/server";
 
@@ -47,7 +48,9 @@ export const GET = withWorkspace(
           include: {
             senderPartner: true,
             senderUser: true,
-            attachments: true,
+            attachments: {
+              orderBy: messageAttachmentsOrderBy,
+            },
           },
           orderBy: {
             [sortBy]: sortOrder,

apps/web/app/(ee)/api/partner-profile/messages/route.ts

@@ -4,6 +4,7 @@ import {
   ProgramMessagesSchema,
   getProgramMessagesQuerySchema,
 } from "@/lib/messages/schemas";
+import { messageAttachmentsOrderBy } from "@/lib/messages/utils";
 import { prisma } from "@/lib/prisma";
 import { NextResponse } from "next/server";
 
@@ -78,7 +79,9 @@ export const GET = withPartnerProfile(async ({ partner, searchParams }) => {
         include: {
           senderPartner: true,
           senderUser: true,
-          attachments: true,
+          attachments: {
+            orderBy: messageAttachmentsOrderBy,
+          },
         },
         orderBy: {
           [sortBy]: sortOrder,

apps/web/lib/messages/enrich.ts

@@ -1,12 +1,15 @@
+import { sortMessageAttachments } from "@/lib/messages/utils";
 import { storage } from "@/lib/storage";
 import { Message, MessageAttachment } from "@prisma/client";
 
 export async function enrichMessage(
   message: Message & { attachments: MessageAttachment[] },
 ) {
+  const attachments = sortMessageAttachments(message.attachments);
+
   return {
     ...message,
-    attachments: await Promise.all(message.attachments.map(enrichAttachment)),
+    attachments: await Promise.all(attachments.map(enrichAttachment)),
   };
 }
 

apps/web/lib/messages/message-partner.ts

@@ -14,6 +14,10 @@ import * as z from "zod/v4";
 import { authActionClient } from "../actions/safe-action";
 import { throwIfNoPermission } from "../actions/throw-if-no-permission";
 import { MessageSchema, messagePartnerSchema } from "./schemas";
+import {
+  mapMessageAttachmentsForCreate,
+  messageAttachmentsOrderBy,
+} from "./utils";
 
 const schema = messagePartnerSchema
   .extend({
@@ -136,20 +140,16 @@ export const messagePartnerAction = authActionClient
         text,
         ...(attachments.length > 0 && {
           attachments: {
-            create: attachments.map((att) => ({
-              id: createId({ prefix: "msa_" }),
-              storageKey: att.storageKey,
-              name: att.name,
-              size: att.size,
-              type: att.type,
-            })),
+            create: mapMessageAttachmentsForCreate(attachments),
           },
         }),
       },
       include: {
         senderUser: true,
         senderPartner: true,
-        attachments: true,
+        attachments: {
+          orderBy: messageAttachmentsOrderBy,
+        },
       },
     });
 

apps/web/lib/messages/message-program.ts

@@ -8,6 +8,10 @@ import { APP_DOMAIN_WITH_NGROK, INTERCOM_INTEGRATION_ID } from "@dub/utils";
 import { waitUntil } from "@vercel/functions";
 import { authPartnerActionClient } from "../actions/safe-action";
 import { MessageSchema, messageProgramSchema } from "./schemas";
+import {
+  mapMessageAttachmentsForCreate,
+  messageAttachmentsOrderBy,
+} from "./utils";
 
 const schema = messageProgramSchema.refine(
   (data) => data.text.trim().length > 0 || data.attachments.length > 0,
@@ -81,20 +85,16 @@ export const messageProgramAction = authPartnerActionClient
         text,
         ...(attachments.length > 0 && {
           attachments: {
-            create: attachments.map((att) => ({
-              id: createId({ prefix: "msa_" }),
-              storageKey: att.storageKey,
-              name: att.name,
-              size: att.size,
-              type: att.type,
-            })),
+            create: mapMessageAttachmentsForCreate(attachments),
           },
         }),
       },
       include: {
         senderUser: true,
         senderPartner: true,
-        attachments: true,
+        attachments: {
+          orderBy: messageAttachmentsOrderBy,
+        },
       },
     });
 

apps/web/lib/messages/utils.ts

@@ -1,8 +1,42 @@
+import { createId } from "@/lib/api/create-id";
 import {
   ATTACHMENT_MIME_TYPE_LABELS,
   PREVIEWABLE_IMAGE_TYPES,
 } from "./constants";
 
+export const messageAttachmentsOrderBy = { createdAt: "asc" } as const;
+
+type MessageAttachmentInput = {
+  storageKey: string;
+  name: string;
+  size: number;
+  type: string;
+};
+
+export function mapMessageAttachmentsForCreate(
+  attachments: MessageAttachmentInput[],
+) {
+  const base = Date.now();
+
+  return attachments.map((att, index) => ({
+    id: createId({ prefix: "msa_" }),
+    storageKey: att.storageKey,
+    name: att.name,
+    size: att.size,
+    type: att.type,
+    createdAt: new Date(base + index),
+  }));
+}
+
+export function sortMessageAttachments<
+  T extends { createdAt: Date; id: string },
+>(attachments: T[]) {
+  return [...attachments].sort(
+    (a, b) =>
+      a.createdAt.getTime() - b.createdAt.getTime() || a.id.localeCompare(b.id),
+  );
+}
+
 // Normalize a user-supplied file name
 export function sanitizeFileName(name: string): string {
   return name