diff --git a/packages/nextjs/src/config/types.ts b/packages/nextjs/src/config/types.ts
index ffce8a8b0641..fe05624ba15e 100644
--- a/packages/nextjs/src/config/types.ts
+++ b/packages/nextjs/src/config/types.ts
@@ -426,9 +426,12 @@ export type SentryBuildOptions = {
    * Tunnel Sentry requests through this route on the Next.js server, to circumvent ad-blockers blocking Sentry events
    * from being sent. This option should be a path (for example: '/error-monitoring').
    *
+   * - Pass `true` to auto-generate a random, ad-blocker-resistant route for each build
+   * - Pass a string path (e.g., '/monitoring') to use a custom route
+   *
    * NOTE: This feature only works with Next.js 11+
    */
-  tunnelRoute?: string;
+  tunnelRoute?: string | boolean;
 
   /**
    * Tree shakes Sentry SDK logger statements from the bundle.
diff --git a/packages/nextjs/src/config/webpack.ts b/packages/nextjs/src/config/webpack.ts
index 8898b3495ba9..aeef52d4e309 100644
--- a/packages/nextjs/src/config/webpack.ts
+++ b/packages/nextjs/src/config/webpack.ts
@@ -692,7 +692,9 @@ function addValueInjectionLoader(
   const isomorphicValues = {
     // `rewritesTunnel` set by the user in Next.js config
     _sentryRewritesTunnelPath:
-      userSentryOptions.tunnelRoute !== undefined && userNextConfig.output !== 'export'
+      userSentryOptions.tunnelRoute !== undefined &&
+      userNextConfig.output !== 'export' &&
+      typeof userSentryOptions.tunnelRoute === 'string'
         ? `${userNextConfig.basePath ?? ''}${userSentryOptions.tunnelRoute}`
         : undefined,
 
diff --git a/packages/nextjs/src/config/withSentryConfig.ts b/packages/nextjs/src/config/withSentryConfig.ts
index b94ce6187f97..4c6a4fb42ed5 100644
--- a/packages/nextjs/src/config/withSentryConfig.ts
+++ b/packages/nextjs/src/config/withSentryConfig.ts
@@ -75,6 +75,15 @@ export function withSentryConfig<C>(nextConfig?: C, sentryBuildOptions: SentryBu
   }
 }
 
+/**
+ * Generates a random tunnel route path that's less likely to be blocked by ad-blockers
+ */
+function generateRandomTunnelRoute(): string {
+  // Generate a random 8-character alphanumeric string
+  const randomString = Math.random().toString(36).substring(2, 10);
+  return `/${randomString}`;
+}
+
 // Modify the materialized object form of the user's next config by deleting the `sentry` property and wrapping the
 // `webpack` property
 function getFinalConfigObject(
@@ -93,7 +102,14 @@ function getFinalConfigObject(
         );
       }
     } else {
-      setUpTunnelRewriteRules(incomingUserNextConfigObject, userSentryOptions.tunnelRoute);
+      const resolvedTunnelRoute =
+        typeof userSentryOptions.tunnelRoute === 'boolean'
+          ? generateRandomTunnelRoute()
+          : userSentryOptions.tunnelRoute;
+
+      // Update the global options object to use the resolved value everywhere
+      userSentryOptions.tunnelRoute = resolvedTunnelRoute;
+      setUpTunnelRewriteRules(incomingUserNextConfigObject, resolvedTunnelRoute);
     }
   }
 
@@ -363,8 +379,11 @@ function setUpBuildTimeVariables(
 ): void {
   const assetPrefix = userNextConfig.assetPrefix || userNextConfig.basePath || '';
   const basePath = userNextConfig.basePath ?? '';
+
   const rewritesTunnelPath =
-    userSentryOptions.tunnelRoute !== undefined && userNextConfig.output !== 'export'
+    userSentryOptions.tunnelRoute !== undefined &&
+    userNextConfig.output !== 'export' &&
+    typeof userSentryOptions.tunnelRoute === 'string'
       ? `${basePath}${userSentryOptions.tunnelRoute}`
       : undefined;
 
diff --git a/packages/nextjs/test/utils/tunnelRoute.test.ts b/packages/nextjs/test/utils/tunnelRoute.test.ts
index fb228375f1e0..8382e66ca7d4 100644
--- a/packages/nextjs/test/utils/tunnelRoute.test.ts
+++ b/packages/nextjs/test/utils/tunnelRoute.test.ts
@@ -81,3 +81,40 @@ describe('applyTunnelRouteOption()', () => {
     expect(options.tunnel).toBe('/my-error-monitoring-route?o=2222222&p=3333333&r=us');
   });
 });
+
+describe('Random tunnel route generation', () => {
+  it('Works when tunnelRoute is true and generates random-looking paths', () => {
+    globalWithInjectedValues._sentryRewritesTunnelPath = '/abc123def'; // Simulated random path
+    const options: any = {
+      dsn: 'https://11111111111111111111111111111111@o2222222.ingest.sentry.io/3333333',
+    } as BrowserOptions;
+
+    applyTunnelRouteOption(options);
+
+    expect(options.tunnel).toBe('/abc123def?o=2222222&p=3333333');
+    expect(options.tunnel).toMatch(/^\/[a-z0-9]+\?o=2222222&p=3333333$/);
+  });
+
+  it('Works with region DSNs when tunnelRoute is true', () => {
+    globalWithInjectedValues._sentryRewritesTunnelPath = '/x7h9k2m'; // Simulated random path
+    const options: any = {
+      dsn: 'https://11111111111111111111111111111111@o2222222.ingest.eu.sentry.io/3333333',
+    } as BrowserOptions;
+
+    applyTunnelRouteOption(options);
+
+    expect(options.tunnel).toBe('/x7h9k2m?o=2222222&p=3333333&r=eu');
+    expect(options.tunnel).toMatch(/^\/[a-z0-9]+\?o=2222222&p=3333333&r=eu$/);
+  });
+
+  it('Does not apply tunnel when tunnelRoute is false', () => {
+    globalWithInjectedValues._sentryRewritesTunnelPath = undefined;
+    const options: any = {
+      dsn: 'https://11111111111111111111111111111111@o2222222.ingest.sentry.io/3333333',
+    } as BrowserOptions;
+
+    applyTunnelRouteOption(options);
+
+    expect(options.tunnel).toBeUndefined();
+  });
+});