diff --git a/apps/api/package.json b/apps/api/package.json
index e8d4488..a7c8876 100644
--- a/apps/api/package.json
+++ b/apps/api/package.json
@@ -24,6 +24,7 @@
     "nodemailer": "^6.9.16",
     "stripe": "^22.0.0",
     "telnyx": "^1.23.0",
+    "uuid": "^11.0.5",
 
     "zod": "^4.3.6"
   },
@@ -31,6 +32,7 @@
     "@types/node": "^22.10.7",
     "@types/node-cron": "^3.0.11",
     "@types/nodemailer": "^6.4.17",
+    "@types/uuid": "^10.0.0",
     "@vitest/coverage-v8": "^3.2.4",
     "eslint": "^9.18.0",
     "tsx": "^4.19.2",
diff --git a/apps/api/src/routes/webhooks/telnyx.ts b/apps/api/src/routes/webhooks/telnyx.ts
index 723663d..f8393a3 100644
--- a/apps/api/src/routes/webhooks/telnyx.ts
+++ b/apps/api/src/routes/webhooks/telnyx.ts
@@ -3,7 +3,6 @@ import { createHmac } from "crypto";
 import {
   handleMessageReceived,
   handleMessageFinalized,
-  resolveBusinessIdByMessagingNumber,
   TelnyxMessageReceivedPayload,
 } from "../../services/messaging/inbound.js";
 
@@ -45,7 +44,7 @@ telnyxWebhooksRouter.post("/messaging", async (c) => {
     return c.json({ error: "Could not read body" }, 400);
   }
 
-  if (!validateTelnyxSignature(rawBody, signature)) {
+  if (!validateTelnyxSignature(rawBody, signature ?? null)) {
     return c.json({ error: "Invalid signature" }, 401);
   }
 
diff --git a/apps/api/src/services/messaging/__tests__/inbound.test.ts b/apps/api/src/services/messaging/__tests__/inbound.test.ts
index aab629d..76dfeaf 100644
--- a/apps/api/src/services/messaging/__tests__/inbound.test.ts
+++ b/apps/api/src/services/messaging/__tests__/inbound.test.ts
@@ -2,7 +2,6 @@ import { describe, it, expect, vi, beforeEach } from "vitest";
 import {
   findOrCreateConversation,
   upsertMessage,
-  resolveBusinessIdByMessagingNumber,
   handleMessageReceived,
   handleMessageFinalized,
   TelnyxMessageReceivedPayload,
@@ -54,7 +53,7 @@ const makePayload = (
 
 describe("signature validation via route", () => {
   it("returns 401 when telnyx-signature header is missing", async () => {
-    const { telnyxWebhooksRouter } = await import("../../routes/webhooks/telnyx.js");
+    const { telnyxWebhooksRouter } = await import("../../../routes/webhooks/telnyx.js");
     const payload = JSON.stringify(makePayload("message.received", "msg-123", "+1555111", "+1555222"));
     const req = new Request("http://localhost/api/webhooks/telnyx/messaging", {
       method: "POST",
@@ -67,7 +66,7 @@ describe("signature validation via route", () => {
 
   it("returns 401 when signature does not match", async () => {
     process.env.TELNYX_WEBHOOK_SECRET = "test-secret";
-    const { telnyxWebhooksRouter } = await import("../../routes/webhooks/telnyx.js");
+    const { telnyxWebhooksRouter } = await import("../../../routes/webhooks/telnyx.js");
     const payload = JSON.stringify(makePayload("message.received", "msg-123", "+1555111", "+1555222"));
     const req = new Request("http://localhost/api/webhooks/telnyx/messaging", {
       method: "POST",
diff --git a/apps/api/src/services/messaging/__tests__/outbound.test.ts b/apps/api/src/services/messaging/__tests__/outbound.test.ts
index d051c29..0e8545f 100644
--- a/apps/api/src/services/messaging/__tests__/outbound.test.ts
+++ b/apps/api/src/services/messaging/__tests__/outbound.test.ts
@@ -4,7 +4,7 @@ const mockSendSms = vi.fn();
 const mockGetDb = vi.fn();
 const mockUuidv4 = vi.fn();
 
-vi.mock("../sms.js", () => ({
+vi.mock("../../sms.js", () => ({
   sendSms: mockSendSms,
 }));
 
@@ -24,9 +24,6 @@ vi.mock("uuid", () => ({
 
 const { sendMessage, MissingTenantPhoneNumberError } = await import("../outbound.ts");
 
-const mockEq = (a: unknown, b: unknown) => [a, b];
-const mockAnd = (...args: unknown[]) => args;
-
 describe("sendMessage", () => {
   beforeEach(() => {
     vi.clearAllMocks();
diff --git a/apps/api/src/services/messaging/inbound.ts b/apps/api/src/services/messaging/inbound.ts
index d6d683e..723afb0 100644
--- a/apps/api/src/services/messaging/inbound.ts
+++ b/apps/api/src/services/messaging/inbound.ts
@@ -1,5 +1,4 @@
 import { getDb, conversations, messages, businessSettings, eq, and, sql } from "@groombook/db";
-import { messageDirectionEnum, messageStatusEnum } from "@groombook/db";
 import { v4 as uuidv4 } from "uuid";
 
 export interface TelnyxMessageReceivedPayload {
@@ -20,14 +19,6 @@ export interface TelnyxMessageReceivedPayload {
   };
 }
 
-function buildFindOrCreateConversationParams(businessId: string, clientPhone: string, businessNumber: string) {
-  return {
-    businessId,
-    externalNumber: clientPhone,
-    businessNumber,
-  };
-}
-
 export async function findOrCreateConversation(
   businessId: string,
   clientPhone: string,
@@ -73,6 +64,8 @@ export async function findOrCreateConversation(
     })
     .returning({ id: conversations.id, clientId: conversations.clientId });
 
+  if (!created) throw new Error("Failed to create conversation");
+
   return { id: created.id, clientId: created.clientId };
 }
 
@@ -109,6 +102,8 @@ export async function upsertMessage(
     })
     .returning({ id: messages.id });
 
+  if (!inserted) throw new Error("Failed to insert message");
+
   return { id: inserted.id, isNew: true };
 }
 
@@ -184,4 +179,4 @@ export async function handleMessageFinalized(payload: TelnyxMessageReceivedPaylo
   }
 
   return { messageId: existing.id, newStatus };
-}
\ No newline at end of file
+}
diff --git a/apps/api/src/services/messaging/outbound.ts b/apps/api/src/services/messaging/outbound.ts
index 320d78b..9b2896e 100644
--- a/apps/api/src/services/messaging/outbound.ts
+++ b/apps/api/src/services/messaging/outbound.ts
@@ -66,6 +66,8 @@ async function findOrCreateConversation(
     })
     .returning({ id: conversations.id });
 
+  if (!created) throw new Error("Failed to create conversation");
+
   return { id: created.id };
 }
 
@@ -115,6 +117,8 @@ export async function sendMessage(opts: SendMessageOptions): Promise<SendMessage
     })
     .returning({ id: messages.id });
 
+  if (!queuedMessage) throw new Error("Failed to insert queued message");
+
   try {
     const result = await sendSms(to, body, mediaUrls);
 
diff --git a/packages/db/src/schema.ts b/packages/db/src/schema.ts
index f1d74b3..1371cd6 100644
--- a/packages/db/src/schema.ts
+++ b/packages/db/src/schema.ts
@@ -477,6 +477,7 @@ export const messages = pgTable(
     createdAt: timestamp("created_at").notNull().defaultNow(),
     deliveredAt: timestamp("delivered_at"),
     readByClientAt: timestamp("read_by_client_at"),
+    updatedAt: timestamp("updated_at").notNull().defaultNow(),
   },
   (t) => [
     index("idx_messages_conversation_id_created_at").on(