Merge pull request #836 from elie222/fix/outlook-webhook

Author: elie222

apps/web/__tests__/outlook-operations.test.ts

@@ -13,9 +13,11 @@
  */
 
 import { describe, test, expect, beforeAll, vi } from "vitest";
+import { NextRequest } from "next/server";
 import prisma from "@/utils/prisma";
 import { createEmailProvider } from "@/utils/email/provider";
 import type { OutlookProvider } from "@/utils/email/microsoft";
+import { webhookBodySchema } from "@/app/api/outlook/webhook/types";
 
 // ============================================
 // TEST DATA - SET VIA ENVIRONMENT VARIABLES
@@ -24,10 +26,17 @@ const TEST_OUTLOOK_EMAIL = process.env.TEST_OUTLOOK_EMAIL;
 const TEST_CONVERSATION_ID =
  process.env.TEST_CONVERSATION_ID ||
  "AQQkADAwATNiZmYAZS05YWEAYy1iNWY0LTAwAi0wMAoAEABuo-fmt9KvQ4u55KlWB32H"; // Real conversation ID from demoinboxzero@outlook.com
+const TEST_MESSAGE_ID =
+ process.env.TEST_MESSAGE_ID ||
+ "AQMkADAwATNiZmYAZS05YWEAYy1iNWY0LTAwAi0wMAoARgAAA-ybH4V64nRKkgXhv9H-GEkHAP38WoVoPXRMilGF27prOB8AAAIBDAAAAP38WoVoPXRMilGF27prOB8AAABGAqbwAAAA"; // Real message ID from demoinboxzero@outlook.com
 const TEST_CATEGORY_NAME = process.env.TEST_CATEGORY_NAME || "To Reply";
 
 vi.mock("server-only", () => ({}));
 
+vi.mock("@/utils/redis/message-processing", () => ({
+ markMessageAsProcessing: vi.fn().mockResolvedValue(true),
+}));
+
 describe.skipIf(!TEST_OUTLOOK_EMAIL)(
  "Outlook Operations Integration Tests",
  () => {
@@ -275,3 +284,169 @@ describe.skipIf(!TEST_OUTLOOK_EMAIL)(
  });
  },
 );
+
+// ============================================
+// WEBHOOK PAYLOAD TESTS
+// ============================================
+describe.skipIf(!TEST_OUTLOOK_EMAIL)("Outlook Webhook Payload", () => {
+ test("should validate real webhook payload structure", () => {
+ const realWebhookPayload = {
+ value: [
+ {
+ subscriptionId: "d2d593e1-9600-4f72-8cd3-dfa04c707f9e",
+ subscriptionExpirationDateTime: "2025-10-09T15:32:19.8+00:00",
+ changeType: "updated",
+ resource:
+ "Users/faa95128258c6335/Messages/AQMkADAwATNiZmYAZS05YWEAYy1iNWY0LTAwAi0wMAoARgAAA-ybH4V64nRKkgXhv9H-GEkHAP38WoVoPXRMilGF27prOB8AAAIBDAAAAP38WoVoPXRMilGF27prOB8AAABGAqbwAAAA",
+ resourceData: {
+ "@odata.type": "#Microsoft.Graph.Message",
+ "@odata.id":
+ "Users/faa95128258c6335/Messages/AQMkADAwATNiZmYAZS05YWEAYy1iNWY0LTAwAi0wMAoARgAAA-ybH4V64nRKkgXhv9H-GEkHAP38WoVoPXRMilGF27prOB8AAAIBDAAAAP38WoVoPXRMilGF27prOB8AAABGAqbwAAAA",
+ "@odata.etag": 'W/"CQAAABYAAAD9/FqFaD10TIpRhdu6azgfAABF+9hk"',
+ id: "AQMkADAwATNiZmYAZS05YWEAYy1iNWY0LTAwAi0wMAoARgAAA-ybH4V64nRKkgXhv9H-GEkHAP38WoVoPXRMilGF27prOB8AAAIBDAAAAP38WoVoPXRMilGF27prOB8AAABGAqbwAAAA",
+ },
+ clientState: "05338492cb69f2facfe870450308f802",
+ tenantId: "",
+ },
+ ],
+ };
+
+ // Validate against our schema
+ const result = webhookBodySchema.safeParse(realWebhookPayload);
+
+ expect(result.success).toBe(true);
+ });
+
+ test("should process webhook and fetch conversationId from message", async () => {
+ // Clean slate: delete any existing executedRules for this message
+ const emailAccount = await prisma.emailAccount.findUniqueOrThrow({
+ where: { email: TEST_OUTLOOK_EMAIL },
+ });
+
+ await prisma.executedRule.deleteMany({
+ where: {
+ emailAccountId: emailAccount.id,
+ messageId: TEST_MESSAGE_ID,
+ },
+ });
+
+ // This test requires a real Outlook account
+ const { POST } = await import("@/app/api/outlook/webhook/route");
+
+ const realWebhookPayload = {
+ value: [
+ {
+ subscriptionId: "d2d593e1-9600-4f72-8cd3-dfa04c707f9e",
+ subscriptionExpirationDateTime: "2025-10-09T15:32:19.8+00:00",
+ changeType: "updated",
+ resource: `Users/faa95128258c6335/Messages/${TEST_MESSAGE_ID}`,
+ resourceData: {
+ "@odata.type": "#Microsoft.Graph.Message",
+ "@odata.id": `Users/faa95128258c6335/Messages/${TEST_MESSAGE_ID}`,
+ "@odata.etag": 'W/"CQAAABYAAAD9/FqFaD10TIpRhdu6azgfAABF+9hk"',
+ id: TEST_MESSAGE_ID,
+ },
+ clientState: process.env.MICROSOFT_WEBHOOK_CLIENT_STATE,
+ tenantId: "",
+ },
+ ],
+ };
+
+ // Create a mock Request object
+ const mockRequest = new NextRequest(
+ "http://localhost:3000/api/outlook/webhook",
+ {
+ method: "POST",
+ headers: {
+ "Content-Type": "application/json",
+ },
+ body: JSON.stringify(realWebhookPayload),
+ },
+ );
+
+ // Call the webhook handler
+ const response = await POST(mockRequest, {
+ params: new Promise(() => ({})),
+ });
+
+ // Verify webhook processed successfully
+ expect(response.status).toBe(200);
+
+ const responseData = await response.json();
+ expect(responseData).toEqual({ ok: true });
+
+ console.log(" ✅ Webhook processed successfully");
+
+ // Verify an executedRule was created for this message
+ const thirtySecondsAgo = new Date(Date.now() - 30_000);
+
+ const executedRule = await prisma.executedRule.findFirst({
+ where: {
+ messageId: TEST_MESSAGE_ID,
+ createdAt: {
+ gte: thirtySecondsAgo,
+ },
+ },
+ include: {
+ rule: {
+ select: {
+ name: true,
+ },
+ },
+ actionItems: {
+ where: {
+ draftId: {
+ not: null,
+ },
+ },
+ },
+ },
+ });
+
+ expect(executedRule).not.toBeNull();
+ expect(executedRule).toBeDefined();
+
+ if (!executedRule) {
+ throw new Error("ExecutedRule is null");
+ }
+
+ console.log(" ✅ ExecutedRule created successfully");
+ console.log(` Rule: ${executedRule.rule?.name || "(no rule)"}`);
+ console.log(` Rule ID: ${executedRule.ruleId || "(no rule id)"}`);
+
+ // Check if a draft was created
+ const draftAction = executedRule.actionItems.find((a) => a.draftId);
+ if (draftAction?.draftId) {
+ const emailAccount = await prisma.emailAccount.findUniqueOrThrow({
+ where: { email: TEST_OUTLOOK_EMAIL },
+ });
+
+ const provider = (await createEmailProvider({
+ emailAccountId: emailAccount.id,
+ provider: "microsoft",
+ })) as OutlookProvider;
+
+ const draft = await provider.getDraft(draftAction.draftId);
+
+ expect(draft).toBeDefined();
+
+ // Verify draft is actually a reply, not a fresh draft
+ expect(draft?.threadId).toBeTruthy();
+ expect(draft?.threadId).not.toBe("");
+
+ console.log(" ✅ Draft created successfully");
+ console.log(` Draft ID: ${draftAction.draftId}`);
+ console.log(` Thread ID: ${draft?.threadId}`);
+ console.log(` Subject: ${draft?.subject || "(no subject)"}`);
+ console.log(" Content:");
+ console.log(
+ ` ${draft?.textPlain?.substring(0, 200).replace(/\n/g, "\n ") || "(empty)"}`,
+ );
+ if (draft?.textPlain && draft.textPlain.length > 200) {
+ console.log(` ... (${draft.textPlain.length} total characters)`);
+ }
+ } else {
+ console.log(" ℹ️ No draft action found");
+ }
+ }, 30_000);
+});

apps/web/app/api/outlook/webhook/process-history-item.ts

@@ -53,19 +53,20 @@ export async function processHistoryItem(
  logger.info("Getting message", loggerOptions);
 
  try {
- const [parsedMessage, hasExistingRule] = await Promise.all([
- provider.getMessage(messageId),
- prisma.executedRule.findUnique({
- where: {
- unique_emailAccount_thread_message: {
- emailAccountId,
- threadId: resourceData.conversationId || messageId,
- messageId,
- },
+ const parsedMessage = await provider.getMessage(messageId);
+
+ const threadId = parsedMessage.threadId;
+
+ const hasExistingRule = await prisma.executedRule.findUnique({
+ where: {
+ unique_emailAccount_thread_message: {
+ emailAccountId,
+ threadId,
+ messageId,
  },
-  select: { id: true },
- }),
- ]);
+ },
+ select: { id: true },
+ });
 
  // if the rule has already been executed, skip
  if (hasExistingRule) {
@@ -116,7 +117,7 @@ export async function processHistoryItem(
  return processAssistantEmail({
  message: {
  id: messageId,
- threadId: resourceData.conversationId || messageId,
+ threadId,
  headers: {
  from,
  to: to.join(","),
@@ -156,7 +157,7 @@ export async function processHistoryItem(
  parsedMessage,
  provider,
  messageId,
- resourceData.conversationId || undefined,
+ threadId,
  );
  return;
  }
@@ -188,7 +189,7 @@ export async function processHistoryItem(
  const response = await runColdEmailBlocker({
  email: {
  ...emailForLLM,
- threadId: resourceData.conversationId || messageId,
+ threadId,
  date: parsedMessage.date ? new Date(parsedMessage.date) : new Date(),
  },
  provider,
@@ -224,7 +225,7 @@ export async function processHistoryItem(
  provider,
  message: {
  id: messageId,
- threadId: resourceData.conversationId || messageId,
+ threadId,
  headers: {
  from,
  to: to.join(","),

apps/web/app/api/outlook/webhook/types.ts

@@ -16,13 +16,15 @@ export type ProcessHistoryOptions = {
  EmailAccountWithAI;
 };
 
+// https://learn.microsoft.com/en-us/graph/api/resources/resourcedata?view=graph-rest-1.0
 const resourceDataSchema = z
  .object({
- id: z.string(),
- folderId: z.string().nullish(),
- conversationId: z.string().nullish(),
+ "@odata.type": z.string().optional(),
+ "@odata.id": z.string().optional(),
+ "@odata.etag": z.string().optional(),
+ id: z.string(), // The message identifier
  })
- .passthrough(); // Allow additional properties
+ .passthrough(); // Allow additional properties from other notification types
 
 const notificationSchema = z.object({
  subscriptionId: z.string(),

apps/web/utils/outlook/mail.ts

@@ -186,29 +186,34 @@ export async function draftEmail(
  emailAddress: { address: addr },
  }));
 
- const draft = {
- subject: args.subject || originalEmail.headers.subject,
- body: {
- contentType: "html",
- content: html,
- },
- toRecipients: [
- {
- emailAddress: {
- address: recipients.to,
- },
- },
- ],
- ...(ccRecipients.length > 0 ? { ccRecipients } : {}),
- conversationId: originalEmail.threadId,
- isDraft: true,
- };
+ // Use createReply endpoint to create a proper reply draft
+ // This ensures the draft is linked to the original message as a reply
+ const replyDraft: Message = await client
+ .getClient()
+ .api(`/me/messages/${originalEmail.id}/createReply`)
+ .post({});
 
- const result: Message = await client
+ // Update the draft with our content
+ const updatedDraft: Message = await client
  .getClient()
- .api("/me/messages")
- .post(draft);
- return result;
+ .api(`/me/messages/${replyDraft.id}`)
+ .patch({
+ subject: args.subject || originalEmail.headers.subject,
+ body: {
+ contentType: "html",
+ content: html,
+ },
+ toRecipients: [
+ {
+ emailAddress: {
+ address: recipients.to,
+ },
+ },
+ ],
+ ...(ccRecipients.length > 0 ? { ccRecipients } : {}),
+ });
+
+ return updatedDraft;
 }
 
 function convertTextToHtmlParagraphs(text?: string | null): string {

apps/web/utils/outlook/message.ts

@@ -108,7 +108,6 @@ export async function getFolderIds(client: OutlookClient) {
  {} as Record<string, string>,
  );
 
- logger.info("Fetched Outlook folder IDs", { folders: folderIdCache });
  return folderIdCache;
 }
 

version.txt

@@ -1 +1 @@
-v2.15.1
+v2.15.2