diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/.gitignore b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/.gitignore
new file mode 100644
index 000000000000..1521c8b7652b
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/.gitignore
@@ -0,0 +1 @@
+dist
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/.npmrc b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/.npmrc
new file mode 100644
index 000000000000..070f80f05092
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/.npmrc
@@ -0,0 +1,2 @@
+@sentry:registry=http://127.0.0.1:4873
+@sentry-internal:registry=http://127.0.0.1:4873
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/package.json b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/package.json
new file mode 100644
index 000000000000..3df947bb58c5
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/package.json
@@ -0,0 +1,32 @@
+{
+  "name": "node-express-incorrect-instrumentation",
+  "version": "1.0.0",
+  "private": true,
+  "scripts": {
+    "build": "tsc",
+    "start": "node dist/app.js",
+    "test": "playwright test",
+    "clean": "npx rimraf node_modules pnpm-lock.yaml",
+    "test:build": "pnpm install && pnpm build",
+    "test:assert": "pnpm test"
+  },
+  "dependencies": {
+    "@sentry/core": "latest || *",
+    "@sentry/node": "latest || *",
+    "@sentry/types": "latest || *",
+    "@trpc/server": "10.45.2",
+    "@trpc/client": "10.45.2",
+    "@types/express": "4.17.17",
+    "@types/node": "18.15.1",
+    "express": "4.19.2",
+    "typescript": "4.9.5",
+    "zod": "~3.22.4"
+  },
+  "devDependencies": {
+    "@playwright/test": "^1.44.1",
+    "@sentry-internal/test-utils": "link:../../../test-utils"
+  },
+  "volta": {
+    "extends": "../../package.json"
+  }
+}
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/playwright.config.mjs b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/playwright.config.mjs
new file mode 100644
index 000000000000..31f2b913b58b
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/playwright.config.mjs
@@ -0,0 +1,7 @@
+import { getPlaywrightConfig } from '@sentry-internal/test-utils';
+
+const config = getPlaywrightConfig({
+  startCommand: `pnpm start`,
+});
+
+export default config;
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/src/app.ts b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/src/app.ts
new file mode 100644
index 000000000000..2ab5d1ace5a0
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/src/app.ts
@@ -0,0 +1,39 @@
+declare global {
+  namespace globalThis {
+    var transactionIds: string[];
+  }
+}
+
+import express from 'express';
+
+const app = express();
+const port = 3030;
+
+// import and init sentry last for missing instrumentation
+import * as Sentry from '@sentry/node';
+Sentry.init({
+  environment: 'qa', // dynamic sampling bias to keep transactions
+  dsn: process.env.E2E_TEST_DSN,
+  includeLocalVariables: true,
+  debug: !!process.env.DEBUG,
+  tunnel: `http://localhost:3031/`, // proxy server
+  tracesSampleRate: 1,
+});
+
+app.get('/test-exception/:id', function (req, _res) {
+  throw new Error(`This is an exception with id ${req.params.id}`);
+});
+
+Sentry.setupExpressErrorHandler(app);
+
+// @ts-ignore
+app.use(function onError(err, req, res, next) {
+  // The error id is attached to `res.sentry` to be returned
+  // and optionally displayed to the user for support.
+  res.statusCode = 500;
+  res.end(res.sentry + '\n');
+});
+
+app.listen(port, () => {
+  console.log(`Example app listening on port ${port}`);
+});
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/start-event-proxy.mjs b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/start-event-proxy.mjs
new file mode 100644
index 000000000000..3276781a442a
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/start-event-proxy.mjs
@@ -0,0 +1,6 @@
+import { startEventProxyServer } from '@sentry-internal/test-utils';
+
+startEventProxyServer({
+  port: 3031,
+  proxyServerName: 'node-express',
+});
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/tests/instrumentation.test.ts b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/tests/instrumentation.test.ts
new file mode 100644
index 000000000000..f562cb3a5837
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/tests/instrumentation.test.ts
@@ -0,0 +1,20 @@
+import { expect, test } from '@playwright/test';
+import { waitForError } from '@sentry-internal/test-utils';
+
+test('Sends correct context when instrumentation was set up incorrectly', async ({ baseURL }) => {
+  const errorEventPromise = waitForError('node-express', event => {
+    return !event.type && event.exception?.values?.[0]?.value === 'This is an exception with id 123';
+  });
+
+  await fetch(`${baseURL}/test-exception/123`);
+
+  const errorEvent = await errorEventPromise;
+
+  expect(errorEvent.exception?.values).toHaveLength(1);
+  expect(errorEvent.exception?.values?.[0]?.value).toBe('This is an exception with id 123');
+
+  expect(errorEvent.contexts?.missing_instrumentation).toEqual({
+    package: 'express',
+    'javascript.is_cjs': true,
+  });
+});
diff --git a/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/tsconfig.json b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/tsconfig.json
new file mode 100644
index 000000000000..8cb64e989ed9
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/node-express-incorrect-instrumentation/tsconfig.json
@@ -0,0 +1,10 @@
+{
+  "compilerOptions": {
+    "types": ["node"],
+    "esModuleInterop": true,
+    "lib": ["es2018"],
+    "strict": true,
+    "outDir": "dist"
+  },
+  "include": ["src/**/*.ts"]
+}
diff --git a/packages/node/src/utils/createMissingInstrumentationContext.ts b/packages/node/src/utils/createMissingInstrumentationContext.ts
new file mode 100644
index 000000000000..849e49e8b8e2
--- /dev/null
+++ b/packages/node/src/utils/createMissingInstrumentationContext.ts
@@ -0,0 +1,7 @@
+import type { MissingInstrumentationContext } from '@sentry/types';
+import { isCjs } from './commonjs';
+
+export const createMissingInstrumentationContext = (pkg: string): MissingInstrumentationContext => ({
+  package: pkg,
+  'javascript.is_cjs': isCjs(),
+});
diff --git a/packages/node/src/utils/ensureIsWrapped.ts b/packages/node/src/utils/ensureIsWrapped.ts
index 8cf85b39d545..05185a293bed 100644
--- a/packages/node/src/utils/ensureIsWrapped.ts
+++ b/packages/node/src/utils/ensureIsWrapped.ts
@@ -1,7 +1,8 @@
 import { isWrapped } from '@opentelemetry/core';
-import { hasTracingEnabled, isEnabled } from '@sentry/core';
+import { getGlobalScope, hasTracingEnabled, isEnabled } from '@sentry/core';
 import { consoleSandbox } from '@sentry/utils';
 import { isCjs } from './commonjs';
+import { createMissingInstrumentationContext } from './createMissingInstrumentationContext';
 
 /**
  * Checks and warns if a framework isn't wrapped by opentelemetry.
@@ -24,5 +25,7 @@ export function ensureIsWrapped(
         );
       }
     });
+
+    getGlobalScope().setContext('missing_instrumentation', createMissingInstrumentationContext(name));
   }
 }
diff --git a/packages/types/src/context.ts b/packages/types/src/context.ts
index 0344dd179787..10fc61420e25 100644
--- a/packages/types/src/context.ts
+++ b/packages/types/src/context.ts
@@ -119,3 +119,8 @@ export interface CloudResourceContext extends Record<string, unknown> {
 export interface ProfileContext extends Record<string, unknown> {
   profile_id: string;
 }
+
+export interface MissingInstrumentationContext extends Record<string, unknown> {
+  package: string;
+  ['javascript.is_cjs']?: boolean;
+}
diff --git a/packages/types/src/index.ts b/packages/types/src/index.ts
index a7cf18056eb6..8f7fdce74c33 100644
--- a/packages/types/src/index.ts
+++ b/packages/types/src/index.ts
@@ -18,6 +18,7 @@ export type {
   CultureContext,
   TraceContext,
   CloudResourceContext,
+  MissingInstrumentationContext,
 } from './context';
 export type { DataCategory } from './datacategory';
 export type { DsnComponents, DsnLike, DsnProtocol } from './dsn';