diff --git a/packages/nextjs/src/common/wrapApiHandlerWithSentryVercelCrons.ts b/packages/nextjs/src/common/wrapApiHandlerWithSentryVercelCrons.ts
index abf707dd5f2c..3b9bc8ca7045 100644
--- a/packages/nextjs/src/common/wrapApiHandlerWithSentryVercelCrons.ts
+++ b/packages/nextjs/src/common/wrapApiHandlerWithSentryVercelCrons.ts
@@ -3,6 +3,11 @@ import type { NextApiRequest } from 'next';
 
 import type { VercelCronsConfig } from './types';
 
+type EdgeRequest = {
+  nextUrl: URL;
+  headers: Headers;
+};
+
 /**
  * Wraps a function with Sentry crons instrumentation by automaticaly sending check-ins for the given Vercel crons config.
  */
@@ -11,19 +16,21 @@ export function wrapApiHandlerWithSentryVercelCrons<F extends (...args: any[]) =
   vercelCronsConfig: VercelCronsConfig,
 ): F {
   return new Proxy(handler, {
-    apply: (originalFunction, thisArg, args: [NextApiRequest | undefined] | undefined) => {
+    apply: (originalFunction, thisArg, args: [NextApiRequest | EdgeRequest | undefined] | undefined) => {
       return runWithAsyncContext(() => {
         if (!args || !args[0]) {
           return originalFunction.apply(thisArg, args);
         }
+
         const [req] = args;
 
         let maybePromiseResult;
-        const cronsKey = req.url;
+        const cronsKey = 'nextUrl' in req ? req.nextUrl.pathname : req.url;
+        const userAgentHeader = 'nextUrl' in req ? req.headers.get('user-agent') : req.headers['user-agent'];
 
         if (
           !vercelCronsConfig || // do nothing if vercel crons config is missing
-          !req.headers['user-agent']?.includes('vercel-cron') // do nothing if endpoint is not called from vercel crons
+          !userAgentHeader?.includes('vercel-cron') // do nothing if endpoint is not called from vercel crons
         ) {
           return originalFunction.apply(thisArg, args);
         }
@@ -42,7 +49,6 @@ export function wrapApiHandlerWithSentryVercelCrons<F extends (...args: any[]) =
             status: 'in_progress',
           },
           {
-            checkinMargin: 2, // two minutes - in case Vercel has a blip
             maxRuntime: 60 * 12, // (minutes) so 12 hours - just a very high arbitrary number since we don't know the actual duration of the users cron job
             schedule: {
               type: 'crontab',
diff --git a/packages/nextjs/src/config/loaders/wrappingLoader.ts b/packages/nextjs/src/config/loaders/wrappingLoader.ts
index 2cd83f672fd5..28c8f58b2eb9 100644
--- a/packages/nextjs/src/config/loaders/wrappingLoader.ts
+++ b/packages/nextjs/src/config/loaders/wrappingLoader.ts
@@ -5,6 +5,7 @@ import * as fs from 'fs';
 import * as path from 'path';
 import { rollup } from 'rollup';
 
+import type { VercelCronsConfig } from '../../common/types';
 import type { LoaderThis } from './types';
 
 // Just a simple placeholder to make referencing module consistent
@@ -44,6 +45,7 @@ type LoaderOptions = {
   excludeServerRoutes: Array<RegExp | string>;
   wrappingTargetKind: 'page' | 'api-route' | 'middleware' | 'server-component';
   sentryConfigFilePath?: string;
+  vercelCronsConfig?: VercelCronsConfig;
 };
 
 function moduleExists(id: string): boolean {
@@ -74,6 +76,7 @@ export default function wrappingLoader(
     excludeServerRoutes = [],
     wrappingTargetKind,
     sentryConfigFilePath,
+    vercelCronsConfig,
   } = 'getOptions' in this ? this.getOptions() : this.query;
 
   this.async();
@@ -113,6 +116,8 @@ export default function wrappingLoader(
       throw new Error(`Invariant: Could not get template code of unknown kind "${wrappingTargetKind}"`);
     }
 
+    templateCode = templateCode.replace(/__VERCEL_CRONS_CONFIGURATION__/g, JSON.stringify(vercelCronsConfig));
+
     // Inject the route and the path to the file we're wrapping into the template
     templateCode = templateCode.replace(/__ROUTE__/g, parameterizedPagesRoute.replace(/\\/g, '\\\\'));
   } else if (wrappingTargetKind === 'server-component') {
diff --git a/packages/nextjs/src/config/templates/apiWrapperTemplate.ts b/packages/nextjs/src/config/templates/apiWrapperTemplate.ts
index 91cf5ef1e0c6..0eccf3024a76 100644
--- a/packages/nextjs/src/config/templates/apiWrapperTemplate.ts
+++ b/packages/nextjs/src/config/templates/apiWrapperTemplate.ts
@@ -13,6 +13,7 @@ import * as origModule from '__SENTRY_WRAPPING_TARGET_FILE__';
 import * as Sentry from '@sentry/nextjs';
 import type { PageConfig } from 'next';
 
+import type { VercelCronsConfig } from '../../common/types';
 // We import this from `wrappers` rather than directly from `next` because our version can work simultaneously with
 // multiple versions of next. See note in `wrappers/types` for more.
 import type { NextApiHandler } from '../../server/types';
@@ -54,7 +55,19 @@ export const config = {
   },
 };
 
-export default userProvidedHandler ? Sentry.wrapApiHandlerWithSentry(userProvidedHandler, '__ROUTE__') : undefined;
+declare const __VERCEL_CRONS_CONFIGURATION__: VercelCronsConfig;
+
+let wrappedHandler = userProvidedHandler;
+
+if (wrappedHandler) {
+  wrappedHandler = Sentry.wrapApiHandlerWithSentry(wrappedHandler, '__ROUTE__');
+}
+
+if (wrappedHandler && __VERCEL_CRONS_CONFIGURATION__) {
+  wrappedHandler = Sentry.wrapApiHandlerWithSentryVercelCrons(wrappedHandler, __VERCEL_CRONS_CONFIGURATION__);
+}
+
+export default wrappedHandler;
 
 // Re-export anything exported by the page module we're wrapping. When processing this code, Rollup is smart enough to
 // not include anything whose name matchs something we've explicitly exported above.
diff --git a/packages/nextjs/src/config/types.ts b/packages/nextjs/src/config/types.ts
index f2156382e6f3..28f70d62dc05 100644
--- a/packages/nextjs/src/config/types.ts
+++ b/packages/nextjs/src/config/types.ts
@@ -133,6 +133,13 @@ export type UserSentryOptions = {
    * Tree shakes Sentry SDK logger statements from the bundle.
    */
   disableLogger?: boolean;
+
+  /**
+   * Automatically create cron monitors in Sentry for your Vercel Cron Jobs if configured via `vercel.json`.
+   *
+   * Defaults to `true`.
+   */
+  automaticVercelMonitors?: boolean;
 };
 
 export type NextConfigFunction = (phase: string, defaults: { defaultConfig: NextConfigObject }) => NextConfigObject;
diff --git a/packages/nextjs/src/config/webpack.ts b/packages/nextjs/src/config/webpack.ts
index 73fb60660451..0bb42f98b7ec 100644
--- a/packages/nextjs/src/config/webpack.ts
+++ b/packages/nextjs/src/config/webpack.ts
@@ -7,6 +7,7 @@ import * as chalk from 'chalk';
 import * as fs from 'fs';
 import * as path from 'path';
 
+import type { VercelCronsConfig } from '../common/types';
 // Note: If you need to import a type from Webpack, do it in `types.ts` and export it from there. Otherwise, our
 // circular dependency check thinks this file is importing from itself. See https://github.com/pahen/madge/issues/306.
 import type {
@@ -163,6 +164,31 @@ export function constructWebpackConfigFunction(
         ],
       });
 
+      let vercelCronsConfig: VercelCronsConfig = undefined;
+      try {
+        if (process.env.VERCEL && userSentryOptions.automaticVercelMonitors !== false) {
+          // eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
+          vercelCronsConfig = JSON.parse(fs.readFileSync(path.join(process.cwd(), 'vercel.json'), 'utf8')).crons;
+          if (vercelCronsConfig) {
+            logger.info(
+              `${chalk.cyan(
+                'info',
+              )} - Creating Sentry cron monitors for your Vercel Cron Jobs. You can disable this feature by setting the ${chalk.bold.cyan(
+                'automaticVercelMonitors',
+              )} option to false in you Next.js config.`,
+            );
+          }
+        }
+      } catch (e) {
+        // eslint-disable-next-line @typescript-eslint/no-unsafe-member-access
+        if (e.code === 'ENOENT') {
+          // noop if file does not exist
+        } else {
+          // log but noop
+          logger.error(`${chalk.red('error')} - Sentry failed to read vercel.json`, e);
+        }
+      }
+
       // Wrap api routes
       newConfig.module.rules.unshift({
         test: resourcePath => {
@@ -177,6 +203,7 @@ export function constructWebpackConfigFunction(
             loader: path.resolve(__dirname, 'loaders', 'wrappingLoader.js'),
             options: {
               ...staticWrappingLoaderOptions,
+              vercelCronsConfig,
               wrappingTargetKind: 'api-route',
             },
           },
diff --git a/packages/nextjs/src/edge/edgeclient.ts b/packages/nextjs/src/edge/edgeclient.ts
index 64e3d526061c..ce13d6666448 100644
--- a/packages/nextjs/src/edge/edgeclient.ts
+++ b/packages/nextjs/src/edge/edgeclient.ts
@@ -104,6 +104,8 @@ export class EdgeClient extends BaseClient<EdgeClientOptions> {
     }
 
     const envelope = createCheckInEnvelope(serializedCheckIn, this.getSdkMetadata(), tunnel, this.getDsn());
+
+    __DEBUG_BUILD__ && logger.info('Sending checkin:', checkIn.monitorSlug, checkIn.status);
     void this._sendEnvelope(envelope);
     return id;
   }