diff --git a/apps/web/playwright/booking-pages.e2e.ts b/apps/web/playwright/booking-pages.e2e.ts
index 015460d9bb..5d83253fd2 100644
--- a/apps/web/playwright/booking-pages.e2e.ts
+++ b/apps/web/playwright/booking-pages.e2e.ts
@@ -93,10 +93,7 @@ test.describe("free user", () => {
     await page.goto(bookingUrl);
 
     // book same time spot again
-    await bookTimeSlot(page, {
-      /** FIXME: this should be a 409 conflict */
-      expectedStatusCode: 500,
-    });
+    await bookTimeSlot(page, { expectedStatusCode: 409 });
 
     await page.locator("[data-testid=booking-fail]").waitFor({ state: "visible" });
   });
diff --git a/packages/lib/server/defaultResponder.test.ts b/packages/lib/server/defaultResponder.test.ts
index 25276230be..24926ad316 100644
--- a/packages/lib/server/defaultResponder.test.ts
+++ b/packages/lib/server/defaultResponder.test.ts
@@ -1,5 +1,9 @@
 import type { NextApiRequest, NextApiResponse } from "next";
-import { describe, it, expect, vi } from "vitest";
+import { describe, expect, it, vi } from "vitest";
+
+import { ErrorCode } from "@calcom/lib/errorCodes";
+
+import { TRPCError } from "@trpc/server";
 
 import { defaultResponder } from "./defaultResponder";
 
@@ -19,4 +23,18 @@ describe("defaultResponder", () => {
     await defaultResponder(f)(req, res);
     expect(res.json).not.toHaveBeenCalled();
   });
+  it("should respond with status code 409 for NoAvailableUsersFound", async () => {
+    const f = vi.fn().mockRejectedValue(new Error(ErrorCode.NoAvailableUsersFound));
+    const req = {} as NextApiRequest;
+    const res = { status: vi.fn().mockReturnThis(), json: vi.fn() } as unknown as NextApiResponse;
+    await defaultResponder(f)(req, res);
+    expect(res.status).toHaveBeenCalledWith(409);
+  });
+  it("Rate limit should respond with a 429 status code", async () => {
+    const f = vi.fn().mockRejectedValue(new TRPCError({ code: "TOO_MANY_REQUESTS" }));
+    const req = {} as NextApiRequest;
+    const res = { status: vi.fn().mockReturnThis(), json: vi.fn() } as unknown as NextApiResponse;
+    await defaultResponder(f)(req, res);
+    expect(res.status).toHaveBeenCalledWith(429);
+  });
 });
diff --git a/packages/lib/server/defaultResponder.ts b/packages/lib/server/defaultResponder.ts
index 5b5106187a..e6fb0accee 100644
--- a/packages/lib/server/defaultResponder.ts
+++ b/packages/lib/server/defaultResponder.ts
@@ -27,9 +27,9 @@ export function defaultResponder<T>(
       const error = getServerErrorFromUnknown(err);
       // we don't want to report Bad Request errors to Sentry / console
       if (!(error.statusCode >= 400 && error.statusCode < 500)) {
-        console.error(err);
+        console.error(error);
         const captureException = (await import("@sentry/nextjs")).captureException;
-        captureException(err);
+        captureException(error);
       }
       return res
         .status(error.statusCode)
diff --git a/packages/lib/server/getServerErrorFromUnknown.ts b/packages/lib/server/getServerErrorFromUnknown.ts
index ac64f086be..400829b5b0 100644
--- a/packages/lib/server/getServerErrorFromUnknown.ts
+++ b/packages/lib/server/getServerErrorFromUnknown.ts
@@ -3,6 +3,8 @@ import Stripe from "stripe";
 import type { ZodIssue } from "zod";
 import { ZodError } from "zod";
 
+import { ErrorCode } from "@calcom/lib/errorCodes";
+
 import { TRPCError } from "@trpc/server";
 import { getHTTPStatusCodeFromError } from "@trpc/server/http";
 
@@ -70,7 +72,8 @@ export function getServerErrorFromUnknown(cause: unknown): HttpError {
     };
   }
   if (cause instanceof Error) {
-    return getHttpError({ statusCode: 500, cause });
+    const statusCode = getStatusCode(cause);
+    return getHttpError({ statusCode, cause });
   }
   if (typeof cause === "string") {
     // @ts-expect-error https://github.com/tc39/proposal-error-cause
@@ -83,6 +86,34 @@ export function getServerErrorFromUnknown(cause: unknown): HttpError {
   });
 }
 
+function getStatusCode(cause: Error): number {
+  switch (cause.message) {
+    case ErrorCode.RequestBodyWithouEnd:
+    case ErrorCode.MissingPaymentCredential:
+    case ErrorCode.MissingPaymentAppId:
+    case ErrorCode.AvailabilityNotFoundInSchedule:
+      return 400;
+    case ErrorCode.CancelledBookingsCannotBeRescheduled:
+      return 403;
+    case ErrorCode.NoAvailableUsersFound:
+    case ErrorCode.HostsUnavailableForBooking:
+    case ErrorCode.PaymentCreationFailure:
+    case ErrorCode.ChargeCardFailure:
+    case ErrorCode.AlreadySignedUpForBooking:
+    case ErrorCode.BookingSeatsFull:
+    case ErrorCode.NotEnoughAvailableSeats:
+      return 409;
+    case ErrorCode.EventTypeNotFound:
+    case ErrorCode.BookingNotFound:
+      return 404;
+    case ErrorCode.UnableToSubscribeToThePlatform:
+    case ErrorCode.UpdatingOauthClientError:
+    case ErrorCode.CreatingOauthClientError:
+    default:
+      return 500;
+  }
+}
+
 function getHttpError<T extends Error>({ statusCode, cause }: { statusCode: number; cause: T }) {
   const redacted = redactError(cause);
   return new HttpError({ statusCode, message: redacted.message, cause: redacted });