From 57f837b48dd1110db99056de8b223fa6aa4220c3 Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Thu, 28 Mar 2024 14:26:59 +0000
Subject: [PATCH 1/8] feat: Add loader file to node-based SDKs to support ESM

---
 dev-packages/rollup-utils/.eslintrc.cjs       |  5 ++
 .../rollup-utils/code/otelLoaderTemplate.js   |  1 +
 dev-packages/rollup-utils/npmHelpers.mjs      | 40 ++++++++++++++
 nx.json                                       |  2 +-
 packages/astro/package.json                   | 11 +++-
 packages/astro/rollup.npm.config.mjs          |  4 +-
 packages/aws-serverless/package.json          | 11 +++-
 packages/aws-serverless/rollup.npm.config.mjs | 27 +++++-----
 packages/google-cloud-serverless/package.json | 11 +++-
 .../rollup.npm.config.mjs                     |  4 +-
 packages/nextjs/package.json                  |  6 +++
 packages/nextjs/rollup.npm.config.mjs         |  3 +-
 packages/node/package.json                    | 11 +++-
 packages/node/rollup.npm.config.mjs           |  3 +-
 packages/remix/package.json                   |  9 +++-
 packages/remix/rollup.npm.config.mjs          | 27 +++++-----
 yarn.lock                                     | 53 ++++++++++++++++---
 17 files changed, 181 insertions(+), 47 deletions(-)
 create mode 100644 dev-packages/rollup-utils/.eslintrc.cjs
 create mode 100644 dev-packages/rollup-utils/code/otelLoaderTemplate.js

diff --git a/dev-packages/rollup-utils/.eslintrc.cjs b/dev-packages/rollup-utils/.eslintrc.cjs
new file mode 100644
index 000000000000..0939c10d3812
--- /dev/null
+++ b/dev-packages/rollup-utils/.eslintrc.cjs
@@ -0,0 +1,5 @@
+module.exports = {
+  extends: ['../../.eslintrc.js'],
+  ignorePatterns: ['otelLoaderTemplate.js.tmpl'],
+  sourceType: 'module',
+};
diff --git a/dev-packages/rollup-utils/code/otelLoaderTemplate.js b/dev-packages/rollup-utils/code/otelLoaderTemplate.js
new file mode 100644
index 000000000000..b364ef0082c9
--- /dev/null
+++ b/dev-packages/rollup-utils/code/otelLoaderTemplate.js
@@ -0,0 +1 @@
+export * from 'import-in-the-middle/hook.mjs';
diff --git a/dev-packages/rollup-utils/npmHelpers.mjs b/dev-packages/rollup-utils/npmHelpers.mjs
index 86941fc8db29..b08dd8a3b908 100644
--- a/dev-packages/rollup-utils/npmHelpers.mjs
+++ b/dev-packages/rollup-utils/npmHelpers.mjs
@@ -5,9 +5,11 @@
 import * as fs from 'fs';
 import { builtinModules } from 'module';
 import * as path from 'path';
+import { fileURLToPath } from 'url';
 
 import deepMerge from 'deepmerge';
 
+import { defineConfig } from 'rollup';
 import {
   makeCleanupPlugin,
   makeCodeCovPlugin,
@@ -21,6 +23,8 @@ import {
 import { makePackageNodeEsm } from './plugins/make-esm-plugin.mjs';
 import { mergePlugins } from './utils.mjs';
 
+const __dirname = path.dirname(fileURLToPath(import.meta.url));
+
 const packageDotJSON = JSON.parse(fs.readFileSync(path.resolve(process.cwd(), './package.json'), { encoding: 'utf8' }));
 
 export function makeBaseNPMConfig(options = {}) {
@@ -141,3 +145,39 @@ export function makeNPMConfigVariants(baseConfig, options = {}) {
 
   return variantSpecificConfigs.map(variant => deepMerge(baseConfig, variant));
 }
+
+/**
+ * This creates a loader file at the target location as part of the rollup build.
+ * This loader script can then be used in combination with various Node.js flags (like --loader=...) to monkeypatch 3rd party modules.
+ */
+export function makeOtelLoader(outputPath) {
+  const foundLoaderExport = Object.keys(packageDotJSON.exports ?? {}).some(key => {
+    return packageDotJSON?.exports?.[key]?.import?.default === outputPath;
+  });
+  if (!foundLoaderExport) {
+    throw new Error(
+      `You used the makeOtelLoader() rollup utility without specifying the loader inside \`exports[something].import.default\`. Please add "${outputPath}" as a value there (maybe check for typos - it needs to be "${outputPath}" exactly).`,
+    );
+  }
+
+  const foundImportInTheMiddleDep = Object.keys(packageDotJSON.dependencies ?? {}).some(key => {
+    return key === 'import-in-the-middle' && packageDotJSON?.dependencies?.[key] === '1.7.1';
+  });
+  if (!foundImportInTheMiddleDep) {
+    throw new Error(
+      `You used the makeOtelLoader() rollup utility but didn't specify the "import-in-the-middle": "1.7.1" dependency in ${path.resolve(
+        process.cwd(),
+        'package.json',
+      )}. Please add it to the dependencies.`,
+    );
+  }
+
+  return defineConfig({
+    input: path.join(__dirname, 'code', 'otelLoaderTemplate.js'),
+    external: ['import-in-the-middle/hook.mjs'],
+    output: {
+      format: 'esm',
+      file: outputPath,
+    },
+  });
+}
diff --git a/nx.json b/nx.json
index 1fe8820b9110..6e87a77ccbbe 100644
--- a/nx.json
+++ b/nx.json
@@ -10,7 +10,7 @@
   },
   "namedInputs": {
     "default": ["{projectRoot}/**/*", "sharedGlobals"],
-    "sharedGlobals": ["{workspaceRoot}/*.js", "{workspaceRoot}/*.json", "{workspaceRoot}/yarn.lock"],
+    "sharedGlobals": ["{workspaceRoot}/*.js", "{workspaceRoot}/*.json", "{workspaceRoot}/yarn.lock", "{workspaceRoot}/dev-packages/rollup-utils/**"],
     "production": ["default", "!{projectRoot}/test/**/*", "!{projectRoot}/**/*.md", "!{projectRoot}/*.tgz"]
   },
   "targetDefaults": {
diff --git a/packages/astro/package.json b/packages/astro/package.json
index 7a08d5fbabf5..55699454253d 100644
--- a/packages/astro/package.json
+++ b/packages/astro/package.json
@@ -21,7 +21,8 @@
     "cjs",
     "esm",
     "types",
-    "types-ts3.8"
+    "types-ts3.8",
+    "register.mjs"
   ],
   "main": "build/cjs/index.client.js",
   "module": "build/esm/index.server.js",
@@ -40,6 +41,11 @@
       "import": "./build/esm/integration/middleware/index.js",
       "require": "./build/cjs/integration/middleware/index.js",
       "types": "./build/types/integration/middleware/index.types.d.ts"
+    },
+    "./register": {
+      "import": {
+        "default": "./build/register.mjs"
+      }
     }
   },
   "publishConfig": {
@@ -54,7 +60,8 @@
     "@sentry/node": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
-    "@sentry/vite-plugin": "^2.14.2"
+    "@sentry/vite-plugin": "^2.14.2",
+    "import-in-the-middle": "1.7.1"
   },
   "devDependencies": {
     "astro": "^3.5.0",
diff --git a/packages/astro/rollup.npm.config.mjs b/packages/astro/rollup.npm.config.mjs
index c485392d0ec7..92762b2b499c 100644
--- a/packages/astro/rollup.npm.config.mjs
+++ b/packages/astro/rollup.npm.config.mjs
@@ -1,4 +1,4 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 
 const variants = makeNPMConfigVariants(
   makeBaseNPMConfig({
@@ -14,4 +14,4 @@ const variants = makeNPMConfigVariants(
   }),
 );
 
-export default variants;
+export default [...variants, makeOtelLoader('./build/register.mjs')];
diff --git a/packages/aws-serverless/package.json b/packages/aws-serverless/package.json
index f341f28809f1..37dd5912227a 100644
--- a/packages/aws-serverless/package.json
+++ b/packages/aws-serverless/package.json
@@ -12,7 +12,8 @@
   "files": [
     "cjs",
     "types",
-    "types-ts3.8"
+    "types-ts3.8",
+    "register.mjs"
   ],
   "main": "build/npm/cjs/index.js",
   "types": "build/npm/types/index.d.ts",
@@ -23,6 +24,11 @@
         "types": "./build/npm/types/index.d.ts",
         "default": "./build/npm/cjs/index.js"
       }
+    },
+    "./register": {
+      "import": {
+        "default": "./build/register.mjs"
+      }
     }
   },
   "typesVersions": {
@@ -41,7 +47,8 @@
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
     "@types/aws-lambda": "^8.10.62",
-    "@types/express": "^4.17.14"
+    "@types/express": "^4.17.14",
+    "import-in-the-middle": "1.7.1"
   },
   "devDependencies": {
     "@types/node": "^14.18.0",
diff --git a/packages/aws-serverless/rollup.npm.config.mjs b/packages/aws-serverless/rollup.npm.config.mjs
index ff28359cfeed..d99f7ded86e8 100644
--- a/packages/aws-serverless/rollup.npm.config.mjs
+++ b/packages/aws-serverless/rollup.npm.config.mjs
@@ -1,13 +1,16 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 
-export default makeNPMConfigVariants(
-  makeBaseNPMConfig({
-    // TODO: `awslambda-auto.ts` is a file which the lambda layer uses to automatically init the SDK. Does it need to be
-    // in the npm package? Is it possible that some people are using it themselves in the same way the layer uses it (in
-    // which case removing it would be a breaking change)? Should it stay here or not?
-    entrypoints: ['src/index.ts', 'src/awslambda-auto.ts'],
-    // packages with bundles have a different build directory structure
-    hasBundles: true,
-  }),
-  { emitEsm: false },
-);
+export default [
+  ...makeNPMConfigVariants(
+    makeBaseNPMConfig({
+      // TODO: `awslambda-auto.ts` is a file which the lambda layer uses to automatically init the SDK. Does it need to be
+      // in the npm package? Is it possible that some people are using it themselves in the same way the layer uses it (in
+      // which case removing it would be a breaking change)? Should it stay here or not?
+      entrypoints: ['src/index.ts', 'src/awslambda-auto.ts'],
+      // packages with bundles have a different build directory structure
+      hasBundles: true,
+    }),
+    { emitEsm: false },
+  ),
+  makeOtelLoader('./build/register.mjs'),
+];
diff --git a/packages/google-cloud-serverless/package.json b/packages/google-cloud-serverless/package.json
index f602834a2341..49d426ed5be0 100644
--- a/packages/google-cloud-serverless/package.json
+++ b/packages/google-cloud-serverless/package.json
@@ -13,7 +13,8 @@
     "cjs",
     "esm",
     "types",
-    "types-ts3.8"
+    "types-ts3.8",
+    "register.mjs"
   ],
   "main": "build/cjs/index.js",
   "types": "build/types/index.d.ts",
@@ -24,6 +25,11 @@
         "types": "./build/types/index.d.ts",
         "default": "./build/cjs/index.js"
       }
+    },
+    "./register": {
+      "import": {
+        "default": "./build/register.mjs"
+      }
     }
   },
   "typesVersions": {
@@ -41,7 +47,8 @@
     "@sentry/node": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
-    "@types/express": "^4.17.14"
+    "@types/express": "^4.17.14",
+    "import-in-the-middle": "1.7.1"
   },
   "devDependencies": {
     "@google-cloud/bigquery": "^5.3.0",
diff --git a/packages/google-cloud-serverless/rollup.npm.config.mjs b/packages/google-cloud-serverless/rollup.npm.config.mjs
index 84a06f2fb64a..2d6da37d7610 100644
--- a/packages/google-cloud-serverless/rollup.npm.config.mjs
+++ b/packages/google-cloud-serverless/rollup.npm.config.mjs
@@ -1,3 +1,3 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 
-export default makeNPMConfigVariants(makeBaseNPMConfig());
+export default [...makeNPMConfigVariants(makeBaseNPMConfig()), makeOtelLoader('./build/register.mjs')];
diff --git a/packages/nextjs/package.json b/packages/nextjs/package.json
index 213958d1fd84..d56947dafda1 100644
--- a/packages/nextjs/package.json
+++ b/packages/nextjs/package.json
@@ -22,6 +22,11 @@
       },
       "node": "./build/cjs/index.server.js",
       "types": "./build/types/index.types.d.ts"
+    },
+    "./register": {
+      "import": {
+        "default": "./build/register.mjs"
+      }
     }
   },
   "typesVersions": {
@@ -44,6 +49,7 @@
     "@sentry/vercel-edge": "8.0.0-alpha.7",
     "@sentry/webpack-plugin": "2.16.0",
     "chalk": "3.0.0",
+    "import-in-the-middle": "1.7.1",
     "resolve": "1.22.8",
     "rollup": "3.29.4",
     "stacktrace-parser": "^0.1.10"
diff --git a/packages/nextjs/rollup.npm.config.mjs b/packages/nextjs/rollup.npm.config.mjs
index 39b79c9593b2..8fc31d35d64f 100644
--- a/packages/nextjs/rollup.npm.config.mjs
+++ b/packages/nextjs/rollup.npm.config.mjs
@@ -1,4 +1,4 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 
 export default [
   ...makeNPMConfigVariants(
@@ -72,4 +72,5 @@ export default [
       },
     }),
   ),
+  makeOtelLoader('./build/register.mjs'),
 ];
diff --git a/packages/node/package.json b/packages/node/package.json
index 885ebe84f0b7..adc2ff570b49 100644
--- a/packages/node/package.json
+++ b/packages/node/package.json
@@ -13,7 +13,8 @@
     "cjs",
     "esm",
     "types",
-    "types-ts3.8"
+    "types-ts3.8",
+    "register.mjs"
   ],
   "main": "build/cjs/index.js",
   "module": "build/esm/index.js",
@@ -29,6 +30,11 @@
         "types": "./build/types/index.d.ts",
         "default": "./build/cjs/index.js"
       }
+    },
+    "./register": {
+      "import": {
+        "default": "./build/register.mjs"
+      }
     }
   },
   "typesVersions": {
@@ -65,7 +71,8 @@
     "@sentry/core": "8.0.0-alpha.7",
     "@sentry/opentelemetry": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
-    "@sentry/utils": "8.0.0-alpha.7"
+    "@sentry/utils": "8.0.0-alpha.7",
+    "import-in-the-middle": "1.7.1"
   },
   "devDependencies": {
     "@types/node": "^14.18.0"
diff --git a/packages/node/rollup.npm.config.mjs b/packages/node/rollup.npm.config.mjs
index 17c0727d7eff..0568e8f32bb4 100644
--- a/packages/node/rollup.npm.config.mjs
+++ b/packages/node/rollup.npm.config.mjs
@@ -1,10 +1,11 @@
 import replace from '@rollup/plugin-replace';
-import { makeBaseNPMConfig, makeNPMConfigVariants } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 import { createAnrWorkerCode } from './rollup.anr-worker.config.mjs';
 
 const { workerRollupConfig, getBase64Code } = createAnrWorkerCode();
 
 export default [
+  makeOtelLoader('./build/register.mjs'),
   // The worker needs to be built first since it's output is used in the main bundle.
   workerRollupConfig,
   ...makeNPMConfigVariants(
diff --git a/packages/remix/package.json b/packages/remix/package.json
index a1684da9f0c4..848cb7d16104 100644
--- a/packages/remix/package.json
+++ b/packages/remix/package.json
@@ -17,7 +17,8 @@
     "esm",
     "types",
     "types-ts3.8",
-    "scripts"
+    "scripts",
+    "register.mjs"
   ],
   "main": "build/cjs/index.server.js",
   "module": "build/esm/index.server.js",
@@ -32,6 +33,11 @@
       },
       "node": "./build/cjs/index.server.js",
       "types": "./build/types/index.types.d.ts"
+    },
+    "./register": {
+      "import": {
+        "default": "./build/register.mjs"
+      }
     }
   },
   "typesVersions": {
@@ -53,6 +59,7 @@
     "@sentry/react": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
+    "import-in-the-middle": "1.7.1",
     "glob": "^10.3.4",
     "yargs": "^17.6.0"
   },
diff --git a/packages/remix/rollup.npm.config.mjs b/packages/remix/rollup.npm.config.mjs
index c588c260c703..4b2b0d1223f1 100644
--- a/packages/remix/rollup.npm.config.mjs
+++ b/packages/remix/rollup.npm.config.mjs
@@ -1,14 +1,17 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 
-export default makeNPMConfigVariants(
-  makeBaseNPMConfig({
-    entrypoints: ['src/index.server.ts', 'src/index.client.tsx'],
-    packageSpecificConfig: {
-      external: ['react-router', 'react-router-dom'],
-      output: {
-        // make it so Rollup calms down about the fact that we're combining default and named exports
-        exports: 'named',
+export default [
+  ...makeNPMConfigVariants(
+    makeBaseNPMConfig({
+      entrypoints: ['src/index.server.ts', 'src/index.client.tsx'],
+      packageSpecificConfig: {
+        external: ['react-router', 'react-router-dom'],
+        output: {
+          // make it so Rollup calms down about the fact that we're combining default and named exports
+          exports: 'named',
+        },
       },
-    },
-  }),
-);
+    }),
+  ),
+  makeOtelLoader('./build/register.mjs'),
+];
diff --git a/yarn.lock b/yarn.lock
index 1c98b5a07dfd..4b8597372bb6 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -6756,8 +6756,17 @@
   dependencies:
     "@types/unist" "*"
 
-"@types/history-4@npm:@types/history@4.7.8", "@types/history-5@npm:@types/history@4.7.8", "@types/history@*":
-  name "@types/history-4"
+"@types/history-4@npm:@types/history@4.7.8":
+  version "4.7.8"
+  resolved "https://registry.yarnpkg.com/@types/history/-/history-4.7.8.tgz#49348387983075705fe8f4e02fb67f7daaec4934"
+  integrity sha512-S78QIYirQcUoo6UJZx9CSP0O2ix9IaeAXwQi26Rhr/+mg7qqPy8TzaxHSUut7eGjL8WmLccT7/MXf304WjqHcA==
+
+"@types/history-5@npm:@types/history@4.7.8":
+  version "4.7.8"
+  resolved "https://registry.yarnpkg.com/@types/history/-/history-4.7.8.tgz#49348387983075705fe8f4e02fb67f7daaec4934"
+  integrity sha512-S78QIYirQcUoo6UJZx9CSP0O2ix9IaeAXwQi26Rhr/+mg7qqPy8TzaxHSUut7eGjL8WmLccT7/MXf304WjqHcA==
+
+"@types/history@*":
   version "4.7.8"
   resolved "https://registry.yarnpkg.com/@types/history/-/history-4.7.8.tgz#49348387983075705fe8f4e02fb67f7daaec4934"
   integrity sha512-S78QIYirQcUoo6UJZx9CSP0O2ix9IaeAXwQi26Rhr/+mg7qqPy8TzaxHSUut7eGjL8WmLccT7/MXf304WjqHcA==
@@ -7137,7 +7146,15 @@
     "@types/history" "^3"
     "@types/react" "*"
 
-"@types/react-router-4@npm:@types/react-router@5.1.14", "@types/react-router-5@npm:@types/react-router@5.1.14":
+"@types/react-router-4@npm:@types/react-router@5.1.14":
+  version "5.1.14"
+  resolved "https://registry.yarnpkg.com/@types/react-router/-/react-router-5.1.14.tgz#e0442f4eb4c446541ad7435d44a97f8fe6df40da"
+  integrity sha512-LAJpqYUaCTMT2anZheoidiIymt8MuX286zoVFPM3DVb23aQBH0mAkFvzpd4LKqiolV8bBtZWT5Qp7hClCNDENw==
+  dependencies:
+    "@types/history" "*"
+    "@types/react" "*"
+
+"@types/react-router-5@npm:@types/react-router@5.1.14":
   version "5.1.14"
   resolved "https://registry.yarnpkg.com/@types/react-router/-/react-router-5.1.14.tgz#e0442f4eb4c446541ad7435d44a97f8fe6df40da"
   integrity sha512-LAJpqYUaCTMT2anZheoidiIymt8MuX286zoVFPM3DVb23aQBH0mAkFvzpd4LKqiolV8bBtZWT5Qp7hClCNDENw==
@@ -25310,8 +25327,7 @@ react-is@^18.0.0:
   dependencies:
     "@remix-run/router" "1.0.2"
 
-"react-router-6@npm:react-router@6.3.0", react-router@6.3.0:
-  name react-router-6
+"react-router-6@npm:react-router@6.3.0":
   version "6.3.0"
   resolved "https://registry.yarnpkg.com/react-router/-/react-router-6.3.0.tgz#3970cc64b4cb4eae0c1ea5203a80334fdd175557"
   integrity sha512-7Wh1DzVQ+tlFjkeo+ujvjSqSJmkt1+8JO+T5xklPlgrh70y7ogx75ODRW0ThWhY7S+6yEDks8TYrtQe/aoboBQ==
@@ -25326,6 +25342,13 @@ react-router-dom@^6.2.2:
     history "^5.2.0"
     react-router "6.3.0"
 
+react-router@6.3.0:
+  version "6.3.0"
+  resolved "https://registry.yarnpkg.com/react-router/-/react-router-6.3.0.tgz#3970cc64b4cb4eae0c1ea5203a80334fdd175557"
+  integrity sha512-7Wh1DzVQ+tlFjkeo+ujvjSqSJmkt1+8JO+T5xklPlgrh70y7ogx75ODRW0ThWhY7S+6yEDks8TYrtQe/aoboBQ==
+  dependencies:
+    history "^5.2.0"
+
 react@^18.0.0:
   version "18.0.0"
   resolved "https://registry.yarnpkg.com/react/-/react-18.0.0.tgz#b468736d1f4a5891f38585ba8e8fb29f91c3cb96"
@@ -27800,7 +27823,7 @@ stringify-object@^3.2.1:
     is-obj "^1.0.1"
     is-regexp "^1.0.0"
 
-"strip-ansi-cjs@npm:strip-ansi@^6.0.1", strip-ansi@^6.0.0, strip-ansi@^6.0.1:
+"strip-ansi-cjs@npm:strip-ansi@^6.0.1":
   version "6.0.1"
   resolved "https://registry.yarnpkg.com/strip-ansi/-/strip-ansi-6.0.1.tgz#9e26c63d30f53443e9489495b2105d37b67a85d9"
   integrity sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==
@@ -27828,6 +27851,13 @@ strip-ansi@^5.1.0, strip-ansi@^5.2.0:
   dependencies:
     ansi-regex "^4.1.0"
 
+strip-ansi@^6.0.0, strip-ansi@^6.0.1:
+  version "6.0.1"
+  resolved "https://registry.yarnpkg.com/strip-ansi/-/strip-ansi-6.0.1.tgz#9e26c63d30f53443e9489495b2105d37b67a85d9"
+  integrity sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==
+  dependencies:
+    ansi-regex "^5.0.1"
+
 strip-ansi@^7.0.1:
   version "7.0.1"
   resolved "https://registry.yarnpkg.com/strip-ansi/-/strip-ansi-7.0.1.tgz#61740a08ce36b61e50e65653f07060d000975fb2"
@@ -30471,7 +30501,16 @@ workerpool@^6.4.0:
   resolved "https://registry.yarnpkg.com/workerpool/-/workerpool-6.4.0.tgz#f8d5cfb45fde32fa3b7af72ad617c3369567a462"
   integrity sha512-i3KR1mQMNwY2wx20ozq2EjISGtQWDIfV56We+yGJ5yDs8jTwQiLLaqHlkBHITlCuJnYlVRmXegxFxZg7gqI++A==
 
-"wrap-ansi-cjs@npm:wrap-ansi@^7.0.0", wrap-ansi@7.0.0, wrap-ansi@^5.1.0, wrap-ansi@^6.2.0, wrap-ansi@^7.0.0, wrap-ansi@^8.1.0:
+"wrap-ansi-cjs@npm:wrap-ansi@^7.0.0":
+  version "7.0.0"
+  resolved "https://registry.yarnpkg.com/wrap-ansi/-/wrap-ansi-7.0.0.tgz#67e145cff510a6a6984bdf1152911d69d2eb9e43"
+  integrity sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==
+  dependencies:
+    ansi-styles "^4.0.0"
+    string-width "^4.1.0"
+    strip-ansi "^6.0.0"
+
+wrap-ansi@7.0.0, wrap-ansi@^5.1.0, wrap-ansi@^6.2.0, wrap-ansi@^7.0.0, wrap-ansi@^8.1.0:
   version "7.0.0"
   resolved "https://registry.yarnpkg.com/wrap-ansi/-/wrap-ansi-7.0.0.tgz#67e145cff510a6a6984bdf1152911d69d2eb9e43"
   integrity sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==

From a9fc29c4db3361beccc1736885c5aa3d456e2b10 Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Thu, 28 Mar 2024 14:44:28 +0000
Subject: [PATCH 2/8] lint

---
 nx.json | 7 ++++++-
 1 file changed, 6 insertions(+), 1 deletion(-)

diff --git a/nx.json b/nx.json
index 6e87a77ccbbe..d4a90a3a6777 100644
--- a/nx.json
+++ b/nx.json
@@ -10,7 +10,12 @@
   },
   "namedInputs": {
     "default": ["{projectRoot}/**/*", "sharedGlobals"],
-    "sharedGlobals": ["{workspaceRoot}/*.js", "{workspaceRoot}/*.json", "{workspaceRoot}/yarn.lock", "{workspaceRoot}/dev-packages/rollup-utils/**"],
+    "sharedGlobals": [
+      "{workspaceRoot}/*.js",
+      "{workspaceRoot}/*.json",
+      "{workspaceRoot}/yarn.lock",
+      "{workspaceRoot}/dev-packages/rollup-utils/**"
+    ],
     "production": ["default", "!{projectRoot}/test/**/*", "!{projectRoot}/**/*.md", "!{projectRoot}/*.tgz"]
   },
   "targetDefaults": {

From 5a137d85f87bceaf3559acd2e85b8b33fded6962 Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Thu, 28 Mar 2024 15:39:39 +0000
Subject: [PATCH 3/8] Add E2E test

---
 .../esm-loader-node-express-app/.npmrc        |   2 +
 .../event-proxy-server.ts                     | 253 ++++++++++++++++++
 .../esm-loader-node-express-app/package.json  |  27 ++
 .../playwright.config.ts                      |  68 +++++
 .../esm-loader-node-express-app/src/app.mjs   |  49 ++++
 .../start-event-proxy.ts                      |   6 +
 .../tests/server.test.ts                      |  33 +++
 7 files changed, 438 insertions(+)
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/.npmrc
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/event-proxy-server.ts
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/playwright.config.ts
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/src/app.mjs
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/start-event-proxy.ts
 create mode 100644 dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts

diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/.npmrc b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/.npmrc
new file mode 100644
index 000000000000..070f80f05092
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/.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/esm-loader-node-express-app/event-proxy-server.ts b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/event-proxy-server.ts
new file mode 100644
index 000000000000..d14ca5cb5e72
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/event-proxy-server.ts
@@ -0,0 +1,253 @@
+import * as fs from 'fs';
+import * as http from 'http';
+import * as https from 'https';
+import type { AddressInfo } from 'net';
+import * as os from 'os';
+import * as path from 'path';
+import * as util from 'util';
+import * as zlib from 'zlib';
+import type { Envelope, EnvelopeItem, Event } from '@sentry/types';
+import { parseEnvelope } from '@sentry/utils';
+
+const readFile = util.promisify(fs.readFile);
+const writeFile = util.promisify(fs.writeFile);
+
+interface EventProxyServerOptions {
+  /** Port to start the event proxy server at. */
+  port: number;
+  /** The name for the proxy server used for referencing it with listener functions */
+  proxyServerName: string;
+}
+
+interface SentryRequestCallbackData {
+  envelope: Envelope;
+  rawProxyRequestBody: string;
+  rawSentryResponseBody: string;
+  sentryResponseStatusCode?: number;
+}
+
+/**
+ * Starts an event proxy server that will proxy events to sentry when the `tunnel` option is used. Point the `tunnel`
+ * option to this server (like this `tunnel: http://localhost:${port option}/`).
+ */
+export async function startEventProxyServer(options: EventProxyServerOptions): Promise<void> {
+  const eventCallbackListeners: Set<(data: string) => void> = new Set();
+
+  const proxyServer = http.createServer((proxyRequest, proxyResponse) => {
+    const proxyRequestChunks: Uint8Array[] = [];
+
+    proxyRequest.addListener('data', (chunk: Buffer) => {
+      proxyRequestChunks.push(chunk);
+    });
+
+    proxyRequest.addListener('error', err => {
+      throw err;
+    });
+
+    proxyRequest.addListener('end', () => {
+      const proxyRequestBody =
+        proxyRequest.headers['content-encoding'] === 'gzip'
+          ? zlib.gunzipSync(Buffer.concat(proxyRequestChunks)).toString()
+          : Buffer.concat(proxyRequestChunks).toString();
+
+      let envelopeHeader = JSON.parse(proxyRequestBody.split('\n')[0]);
+
+      if (!envelopeHeader.dsn) {
+        throw new Error('[event-proxy-server] No dsn on envelope header. Please set tunnel option.');
+      }
+
+      const { origin, pathname, host } = new URL(envelopeHeader.dsn);
+
+      const projectId = pathname.substring(1);
+      const sentryIngestUrl = `${origin}/api/${projectId}/envelope/`;
+
+      proxyRequest.headers.host = host;
+
+      const sentryResponseChunks: Uint8Array[] = [];
+
+      const sentryRequest = https.request(
+        sentryIngestUrl,
+        { headers: proxyRequest.headers, method: proxyRequest.method },
+        sentryResponse => {
+          sentryResponse.addListener('data', (chunk: Buffer) => {
+            proxyResponse.write(chunk, 'binary');
+            sentryResponseChunks.push(chunk);
+          });
+
+          sentryResponse.addListener('end', () => {
+            eventCallbackListeners.forEach(listener => {
+              const rawSentryResponseBody = Buffer.concat(sentryResponseChunks).toString();
+
+              const data: SentryRequestCallbackData = {
+                envelope: parseEnvelope(proxyRequestBody),
+                rawProxyRequestBody: proxyRequestBody,
+                rawSentryResponseBody,
+                sentryResponseStatusCode: sentryResponse.statusCode,
+              };
+
+              listener(Buffer.from(JSON.stringify(data)).toString('base64'));
+            });
+            proxyResponse.end();
+          });
+
+          sentryResponse.addListener('error', err => {
+            throw err;
+          });
+
+          proxyResponse.writeHead(sentryResponse.statusCode || 500, sentryResponse.headers);
+        },
+      );
+
+      sentryRequest.write(Buffer.concat(proxyRequestChunks), 'binary');
+      sentryRequest.end();
+    });
+  });
+
+  const proxyServerStartupPromise = new Promise<void>(resolve => {
+    proxyServer.listen(options.port, () => {
+      resolve();
+    });
+  });
+
+  const eventCallbackServer = http.createServer((eventCallbackRequest, eventCallbackResponse) => {
+    eventCallbackResponse.statusCode = 200;
+    eventCallbackResponse.setHeader('connection', 'keep-alive');
+
+    const callbackListener = (data: string): void => {
+      eventCallbackResponse.write(data.concat('\n'), 'utf8');
+    };
+
+    eventCallbackListeners.add(callbackListener);
+
+    eventCallbackRequest.on('close', () => {
+      eventCallbackListeners.delete(callbackListener);
+    });
+
+    eventCallbackRequest.on('error', () => {
+      eventCallbackListeners.delete(callbackListener);
+    });
+  });
+
+  const eventCallbackServerStartupPromise = new Promise<void>(resolve => {
+    eventCallbackServer.listen(0, () => {
+      const port = String((eventCallbackServer.address() as AddressInfo).port);
+      void registerCallbackServerPort(options.proxyServerName, port).then(resolve);
+    });
+  });
+
+  await eventCallbackServerStartupPromise;
+  await proxyServerStartupPromise;
+  return;
+}
+
+export async function waitForRequest(
+  proxyServerName: string,
+  callback: (eventData: SentryRequestCallbackData) => Promise<boolean> | boolean,
+): Promise<SentryRequestCallbackData> {
+  const eventCallbackServerPort = await retrieveCallbackServerPort(proxyServerName);
+
+  return new Promise<SentryRequestCallbackData>((resolve, reject) => {
+    const request = http.request(`http://localhost:${eventCallbackServerPort}/`, {}, response => {
+      let eventContents = '';
+
+      response.on('error', err => {
+        reject(err);
+      });
+
+      response.on('data', (chunk: Buffer) => {
+        const chunkString = chunk.toString('utf8');
+        chunkString.split('').forEach(char => {
+          if (char === '\n') {
+            const eventCallbackData: SentryRequestCallbackData = JSON.parse(
+              Buffer.from(eventContents, 'base64').toString('utf8'),
+            );
+            const callbackResult = callback(eventCallbackData);
+            if (typeof callbackResult !== 'boolean') {
+              callbackResult.then(
+                match => {
+                  if (match) {
+                    response.destroy();
+                    resolve(eventCallbackData);
+                  }
+                },
+                err => {
+                  throw err;
+                },
+              );
+            } else if (callbackResult) {
+              response.destroy();
+              resolve(eventCallbackData);
+            }
+            eventContents = '';
+          } else {
+            eventContents = eventContents.concat(char);
+          }
+        });
+      });
+    });
+
+    request.end();
+  });
+}
+
+export function waitForEnvelopeItem(
+  proxyServerName: string,
+  callback: (envelopeItem: EnvelopeItem) => Promise<boolean> | boolean,
+): Promise<EnvelopeItem> {
+  return new Promise((resolve, reject) => {
+    waitForRequest(proxyServerName, async eventData => {
+      const envelopeItems = eventData.envelope[1];
+      for (const envelopeItem of envelopeItems) {
+        if (await callback(envelopeItem)) {
+          resolve(envelopeItem);
+          return true;
+        }
+      }
+      return false;
+    }).catch(reject);
+  });
+}
+
+export function waitForError(
+  proxyServerName: string,
+  callback: (transactionEvent: Event) => Promise<boolean> | boolean,
+): Promise<Event> {
+  return new Promise((resolve, reject) => {
+    waitForEnvelopeItem(proxyServerName, async envelopeItem => {
+      const [envelopeItemHeader, envelopeItemBody] = envelopeItem;
+      if (envelopeItemHeader.type === 'event' && (await callback(envelopeItemBody as Event))) {
+        resolve(envelopeItemBody as Event);
+        return true;
+      }
+      return false;
+    }).catch(reject);
+  });
+}
+
+export function waitForTransaction(
+  proxyServerName: string,
+  callback: (transactionEvent: Event) => Promise<boolean> | boolean,
+): Promise<Event> {
+  return new Promise((resolve, reject) => {
+    waitForEnvelopeItem(proxyServerName, async envelopeItem => {
+      const [envelopeItemHeader, envelopeItemBody] = envelopeItem;
+      if (envelopeItemHeader.type === 'transaction' && (await callback(envelopeItemBody as Event))) {
+        resolve(envelopeItemBody as Event);
+        return true;
+      }
+      return false;
+    }).catch(reject);
+  });
+}
+
+const TEMP_FILE_PREFIX = 'event-proxy-server-';
+
+async function registerCallbackServerPort(serverName: string, port: string): Promise<void> {
+  const tmpFilePath = path.join(os.tmpdir(), `${TEMP_FILE_PREFIX}${serverName}`);
+  await writeFile(tmpFilePath, port, { encoding: 'utf8' });
+}
+
+function retrieveCallbackServerPort(serverName: string): Promise<string> {
+  const tmpFilePath = path.join(os.tmpdir(), `${TEMP_FILE_PREFIX}${serverName}`);
+  return readFile(tmpFilePath, 'utf8');
+}
diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json
new file mode 100644
index 000000000000..99dfd693a272
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json
@@ -0,0 +1,27 @@
+{
+  "name": "node-express-app",
+  "version": "1.0.0",
+  "private": true,
+  "scripts": {
+    "start": "node --loader=@sentry/node/register src/app.mjs",
+    "clean": "npx rimraf node_modules,pnpm-lock.yaml",
+    "test:build": "pnpm install",
+    "test:assert": "playwright test"
+  },
+  "dependencies": {
+    "@sentry/node": "latest || *",
+    "@sentry/types": "latest || *",
+    "express": "4.19.2",
+    "@types/express": "4.17.17",
+    "@types/node": "18.15.1",
+    "typescript": "4.9.5"
+  },
+  "devDependencies": {
+    "@playwright/test": "^1.27.1",
+    "ts-node": "10.9.1"
+  },
+  "volta": {
+    "extends": "../../package.json",
+    "node": "18.18.2"
+  }
+}
diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/playwright.config.ts b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/playwright.config.ts
new file mode 100644
index 000000000000..8ac853fd11d0
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/playwright.config.ts
@@ -0,0 +1,68 @@
+import type { PlaywrightTestConfig } from '@playwright/test';
+import { devices } from '@playwright/test';
+
+// Fix urls not resolving to localhost on Node v17+
+// See: https://github.com/axios/axios/issues/3821#issuecomment-1413727575
+import { setDefaultResultOrder } from 'dns';
+setDefaultResultOrder('ipv4first');
+
+const eventProxyPort = 3031;
+const expressPort = 3030;
+
+/**
+ * See https://playwright.dev/docs/test-configuration.
+ */
+const config: PlaywrightTestConfig = {
+  testDir: './tests',
+  /* Maximum time one test can run for. */
+  timeout: 150_000,
+  expect: {
+    /**
+     * Maximum time expect() should wait for the condition to be met.
+     * For example in `await expect(locator).toHaveText();`
+     */
+    timeout: 5000,
+  },
+  /* Run tests in files in parallel */
+  fullyParallel: true,
+  /* Fail the build on CI if you accidentally left test.only in the source code. */
+  forbidOnly: !!process.env.CI,
+  /* Retry on CI only */
+  retries: 0,
+  /* Reporter to use. See https://playwright.dev/docs/test-reporters */
+  reporter: 'list',
+  /* Shared settings for all the projects below. See https://playwright.dev/docs/api/class-testoptions. */
+  use: {
+    /* Maximum time each action such as `click()` can take. Defaults to 0 (no limit). */
+    actionTimeout: 0,
+
+    /* Base URL to use in actions like `await page.goto('/')`. */
+    baseURL: `http://localhost:${expressPort}`,
+  },
+
+  /* Configure projects for major browsers */
+  projects: [
+    {
+      name: 'chromium',
+      use: {
+        ...devices['Desktop Chrome'],
+      },
+    },
+  ],
+
+  /* Run your local dev server before starting the tests */
+  webServer: [
+    {
+      command: 'pnpm ts-node-script start-event-proxy.ts',
+      port: eventProxyPort,
+    },
+    {
+      command: 'pnpm start',
+      port: expressPort,
+      stdout: 'pipe',
+      stderr: 'pipe',
+    },
+  ],
+};
+
+export default config;
diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/src/app.mjs b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/src/app.mjs
new file mode 100644
index 000000000000..8dc36dc7066b
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/src/app.mjs
@@ -0,0 +1,49 @@
+import * as Sentry from '@sentry/node';
+
+Sentry.init({
+  environment: 'qa', // dynamic sampling bias to keep transactions
+  dsn: process.env.E2E_TEST_DSN,
+  debug: true,
+  tunnel: `http://localhost:3031/`, // proxy server
+  tracesSampleRate: 1,
+});
+
+import express from 'express';
+
+const app = express();
+const port = 3030;
+
+app.get('/test-success', function (req, res) {
+  setTimeout(() => {
+    res.status(200).end();
+  }, 100);
+});
+
+app.get('/test-transaction/:param', function (req, res) {
+  setTimeout(() => {
+    res.status(200).end();
+  }, 100);
+});
+
+app.get('/test-error', function (req, res) {
+  Sentry.captureException(new Error('This is an error'));
+  setTimeout(() => {
+    Sentry.flush(2000).then(() => {
+      res.status(200).end();
+    });
+  }, 100);
+});
+
+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/esm-loader-node-express-app/start-event-proxy.ts b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/start-event-proxy.ts
new file mode 100644
index 000000000000..25ef6807cb93
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/start-event-proxy.ts
@@ -0,0 +1,6 @@
+import { startEventProxyServer } from './event-proxy-server';
+
+startEventProxyServer({
+  port: 3031,
+  proxyServerName: 'esm-loader-node-express-app',
+});
diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts
new file mode 100644
index 000000000000..c9cef1a19e70
--- /dev/null
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts
@@ -0,0 +1,33 @@
+import { expect, test } from '@playwright/test';
+import { waitForError, waitForTransaction } from '../event-proxy-server';
+
+test('Should record exceptions captured inside handlers', async ({ request }) => {
+  const errorEventPromise = waitForError('esm-loader-node-express-app', errorEvent => {
+    return !!errorEvent?.exception?.values?.[0]?.value?.includes('This is an error');
+  });
+
+  await request.get('/test-error');
+
+  await expect(errorEventPromise).resolves.toBeDefined();
+});
+
+test('Should record a transaction for a parameterless route', async ({ request }) => {
+  const errorEventPromise = waitForTransaction('esm-loader-node-express-app', transactionEvent => {
+    console.log('txn', transactionEvent.transaction);
+    return transactionEvent?.transaction === 'GET /test-success';
+  });
+
+  await request.get('/test-success');
+
+  await expect(errorEventPromise).resolves.toBeDefined();
+});
+
+test('Should record a transaction for route with aparameters', async ({ request }) => {
+  const errorEventPromise = waitForTransaction('esm-loader-node-express-app', transactionEvent => {
+    return transactionEvent?.transaction === 'GET /test-transaction/:param';
+  });
+
+  await request.get('/test-transaction/1');
+
+  await expect(errorEventPromise).resolves.toBeDefined();
+});

From 39e2c599a0e32d98fde5b9285e6622e2ff89bb62 Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Thu, 28 Mar 2024 15:40:03 +0000
Subject: [PATCH 4/8] rename

---
 .../esm-loader-node-express-app/tests/server.test.ts      | 8 ++++----
 1 file changed, 4 insertions(+), 4 deletions(-)

diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts
index c9cef1a19e70..a41034ca1af4 100644
--- a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/tests/server.test.ts
@@ -12,22 +12,22 @@ test('Should record exceptions captured inside handlers', async ({ request }) =>
 });
 
 test('Should record a transaction for a parameterless route', async ({ request }) => {
-  const errorEventPromise = waitForTransaction('esm-loader-node-express-app', transactionEvent => {
+  const transactionEventPromise = waitForTransaction('esm-loader-node-express-app', transactionEvent => {
     console.log('txn', transactionEvent.transaction);
     return transactionEvent?.transaction === 'GET /test-success';
   });
 
   await request.get('/test-success');
 
-  await expect(errorEventPromise).resolves.toBeDefined();
+  await expect(transactionEventPromise).resolves.toBeDefined();
 });
 
 test('Should record a transaction for route with aparameters', async ({ request }) => {
-  const errorEventPromise = waitForTransaction('esm-loader-node-express-app', transactionEvent => {
+  const transactionEventPromise = waitForTransaction('esm-loader-node-express-app', transactionEvent => {
     return transactionEvent?.transaction === 'GET /test-transaction/:param';
   });
 
   await request.get('/test-transaction/1');
 
-  await expect(errorEventPromise).resolves.toBeDefined();
+  await expect(transactionEventPromise).resolves.toBeDefined();
 });

From 1f370508de8d8acfc1c7221cb397865ee20957ee Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Thu, 28 Mar 2024 15:56:22 +0000
Subject: [PATCH 5/8] better deps

---
 .../code/otelEsmLoaderTemplate.js             |  2 ++
 .../rollup-utils/code/otelLoaderTemplate.js   |  1 -
 .../code/sentryNodeEsmLoaderTemplate.js       |  2 ++
 dev-packages/rollup-utils/npmHelpers.mjs      | 19 ++++++++++++++-----
 packages/astro/package.json                   |  3 +--
 packages/astro/rollup.npm.config.mjs          |  2 +-
 packages/aws-serverless/package.json          |  3 +--
 packages/aws-serverless/rollup.npm.config.mjs |  2 +-
 packages/google-cloud-serverless/package.json |  3 +--
 .../rollup.npm.config.mjs                     |  2 +-
 packages/nextjs/package.json                  |  1 -
 packages/nextjs/rollup.npm.config.mjs         |  2 +-
 packages/node/package.json                    |  3 +--
 packages/node/rollup.npm.config.mjs           |  2 +-
 packages/remix/package.json                   |  1 -
 packages/remix/rollup.npm.config.mjs          |  2 +-
 16 files changed, 28 insertions(+), 22 deletions(-)
 create mode 100644 dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
 delete mode 100644 dev-packages/rollup-utils/code/otelLoaderTemplate.js
 create mode 100644 dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js

diff --git a/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js b/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
new file mode 100644
index 000000000000..117b7ad92cc0
--- /dev/null
+++ b/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
@@ -0,0 +1,2 @@
+import { getFormat, getSource, load, resolve } from '@opentelemetry/instrumentation/hook.mjs';
+export { load, resolve, getFormat, getSource };
diff --git a/dev-packages/rollup-utils/code/otelLoaderTemplate.js b/dev-packages/rollup-utils/code/otelLoaderTemplate.js
deleted file mode 100644
index b364ef0082c9..000000000000
--- a/dev-packages/rollup-utils/code/otelLoaderTemplate.js
+++ /dev/null
@@ -1 +0,0 @@
-export * from 'import-in-the-middle/hook.mjs';
diff --git a/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js b/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
new file mode 100644
index 000000000000..86c4b731472e
--- /dev/null
+++ b/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
@@ -0,0 +1,2 @@
+import { getFormat, getSource, load, resolve } from '@sentry/node/register';
+export { load, resolve, getFormat, getSource };
diff --git a/dev-packages/rollup-utils/npmHelpers.mjs b/dev-packages/rollup-utils/npmHelpers.mjs
index b08dd8a3b908..20cd096efdfa 100644
--- a/dev-packages/rollup-utils/npmHelpers.mjs
+++ b/dev-packages/rollup-utils/npmHelpers.mjs
@@ -150,7 +150,11 @@ export function makeNPMConfigVariants(baseConfig, options = {}) {
  * This creates a loader file at the target location as part of the rollup build.
  * This loader script can then be used in combination with various Node.js flags (like --loader=...) to monkeypatch 3rd party modules.
  */
-export function makeOtelLoader(outputPath) {
+export function makeOtelLoader(outputPath, hookVariant) {
+  if (hookVariant !== 'otel' && hookVariant !== 'sentry-node') {
+    throw new Error('hookVariant is neither "otel" nor "sentry-node". Pick one.');
+  }
+
   const foundLoaderExport = Object.keys(packageDotJSON.exports ?? {}).some(key => {
     return packageDotJSON?.exports?.[key]?.import?.default === outputPath;
   });
@@ -160,12 +164,13 @@ export function makeOtelLoader(outputPath) {
     );
   }
 
+  const requiredDep = hookVariant === 'otel' ? '@opentelemetry/instrumentation' : '@sentry/node';
   const foundImportInTheMiddleDep = Object.keys(packageDotJSON.dependencies ?? {}).some(key => {
-    return key === 'import-in-the-middle' && packageDotJSON?.dependencies?.[key] === '1.7.1';
+    return key === requiredDep;
   });
   if (!foundImportInTheMiddleDep) {
     throw new Error(
-      `You used the makeOtelLoader() rollup utility but didn't specify the "import-in-the-middle": "1.7.1" dependency in ${path.resolve(
+      `You used the makeOtelLoader() rollup utility but didn't specify the "${requiredDep}" dependency in ${path.resolve(
         process.cwd(),
         'package.json',
       )}. Please add it to the dependencies.`,
@@ -173,8 +178,12 @@ export function makeOtelLoader(outputPath) {
   }
 
   return defineConfig({
-    input: path.join(__dirname, 'code', 'otelLoaderTemplate.js'),
-    external: ['import-in-the-middle/hook.mjs'],
+    input: path.join(
+      __dirname,
+      'code',
+      hookVariant === 'otel' ? 'otelEsmLoaderTemplate.js' : 'sentryNodeEsmLoaderTemplate.js',
+    ),
+    external: ['@opentelemetry/instrumentation/hook.mjs', '@sentry/node/register'],
     output: {
       format: 'esm',
       file: outputPath,
diff --git a/packages/astro/package.json b/packages/astro/package.json
index 55699454253d..233b5a903701 100644
--- a/packages/astro/package.json
+++ b/packages/astro/package.json
@@ -60,8 +60,7 @@
     "@sentry/node": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
-    "@sentry/vite-plugin": "^2.14.2",
-    "import-in-the-middle": "1.7.1"
+    "@sentry/vite-plugin": "^2.14.2"
   },
   "devDependencies": {
     "astro": "^3.5.0",
diff --git a/packages/astro/rollup.npm.config.mjs b/packages/astro/rollup.npm.config.mjs
index 92762b2b499c..b5987be16a8c 100644
--- a/packages/astro/rollup.npm.config.mjs
+++ b/packages/astro/rollup.npm.config.mjs
@@ -14,4 +14,4 @@ const variants = makeNPMConfigVariants(
   }),
 );
 
-export default [...variants, makeOtelLoader('./build/register.mjs')];
+export default [...variants, makeOtelLoader('./build/register.mjs', 'sentry-node')];
diff --git a/packages/aws-serverless/package.json b/packages/aws-serverless/package.json
index 37dd5912227a..536c12d1894d 100644
--- a/packages/aws-serverless/package.json
+++ b/packages/aws-serverless/package.json
@@ -47,8 +47,7 @@
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
     "@types/aws-lambda": "^8.10.62",
-    "@types/express": "^4.17.14",
-    "import-in-the-middle": "1.7.1"
+    "@types/express": "^4.17.14"
   },
   "devDependencies": {
     "@types/node": "^14.18.0",
diff --git a/packages/aws-serverless/rollup.npm.config.mjs b/packages/aws-serverless/rollup.npm.config.mjs
index d99f7ded86e8..67ed35f11ab6 100644
--- a/packages/aws-serverless/rollup.npm.config.mjs
+++ b/packages/aws-serverless/rollup.npm.config.mjs
@@ -12,5 +12,5 @@ export default [
     }),
     { emitEsm: false },
   ),
-  makeOtelLoader('./build/register.mjs'),
+  makeOtelLoader('./build/register.mjs', 'sentry-node'),
 ];
diff --git a/packages/google-cloud-serverless/package.json b/packages/google-cloud-serverless/package.json
index 49d426ed5be0..234a72ed1f36 100644
--- a/packages/google-cloud-serverless/package.json
+++ b/packages/google-cloud-serverless/package.json
@@ -47,8 +47,7 @@
     "@sentry/node": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
-    "@types/express": "^4.17.14",
-    "import-in-the-middle": "1.7.1"
+    "@types/express": "^4.17.14"
   },
   "devDependencies": {
     "@google-cloud/bigquery": "^5.3.0",
diff --git a/packages/google-cloud-serverless/rollup.npm.config.mjs b/packages/google-cloud-serverless/rollup.npm.config.mjs
index 2d6da37d7610..4d511654b3b1 100644
--- a/packages/google-cloud-serverless/rollup.npm.config.mjs
+++ b/packages/google-cloud-serverless/rollup.npm.config.mjs
@@ -1,3 +1,3 @@
 import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
 
-export default [...makeNPMConfigVariants(makeBaseNPMConfig()), makeOtelLoader('./build/register.mjs')];
+export default [...makeNPMConfigVariants(makeBaseNPMConfig()), makeOtelLoader('./build/register.mjs', 'sentry-node')];
diff --git a/packages/nextjs/package.json b/packages/nextjs/package.json
index d56947dafda1..02f09cf98743 100644
--- a/packages/nextjs/package.json
+++ b/packages/nextjs/package.json
@@ -49,7 +49,6 @@
     "@sentry/vercel-edge": "8.0.0-alpha.7",
     "@sentry/webpack-plugin": "2.16.0",
     "chalk": "3.0.0",
-    "import-in-the-middle": "1.7.1",
     "resolve": "1.22.8",
     "rollup": "3.29.4",
     "stacktrace-parser": "^0.1.10"
diff --git a/packages/nextjs/rollup.npm.config.mjs b/packages/nextjs/rollup.npm.config.mjs
index 8fc31d35d64f..96931b8f8afb 100644
--- a/packages/nextjs/rollup.npm.config.mjs
+++ b/packages/nextjs/rollup.npm.config.mjs
@@ -72,5 +72,5 @@ export default [
       },
     }),
   ),
-  makeOtelLoader('./build/register.mjs'),
+  makeOtelLoader('./build/register.mjs', 'sentry-node'),
 ];
diff --git a/packages/node/package.json b/packages/node/package.json
index adc2ff570b49..d7b0dc38fba3 100644
--- a/packages/node/package.json
+++ b/packages/node/package.json
@@ -71,8 +71,7 @@
     "@sentry/core": "8.0.0-alpha.7",
     "@sentry/opentelemetry": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
-    "@sentry/utils": "8.0.0-alpha.7",
-    "import-in-the-middle": "1.7.1"
+    "@sentry/utils": "8.0.0-alpha.7"
   },
   "devDependencies": {
     "@types/node": "^14.18.0"
diff --git a/packages/node/rollup.npm.config.mjs b/packages/node/rollup.npm.config.mjs
index 0568e8f32bb4..8e28541d64a9 100644
--- a/packages/node/rollup.npm.config.mjs
+++ b/packages/node/rollup.npm.config.mjs
@@ -5,7 +5,7 @@ import { createAnrWorkerCode } from './rollup.anr-worker.config.mjs';
 const { workerRollupConfig, getBase64Code } = createAnrWorkerCode();
 
 export default [
-  makeOtelLoader('./build/register.mjs'),
+  makeOtelLoader('./build/register.mjs', 'otel'),
   // The worker needs to be built first since it's output is used in the main bundle.
   workerRollupConfig,
   ...makeNPMConfigVariants(
diff --git a/packages/remix/package.json b/packages/remix/package.json
index 848cb7d16104..bf2975485561 100644
--- a/packages/remix/package.json
+++ b/packages/remix/package.json
@@ -59,7 +59,6 @@
     "@sentry/react": "8.0.0-alpha.7",
     "@sentry/types": "8.0.0-alpha.7",
     "@sentry/utils": "8.0.0-alpha.7",
-    "import-in-the-middle": "1.7.1",
     "glob": "^10.3.4",
     "yargs": "^17.6.0"
   },
diff --git a/packages/remix/rollup.npm.config.mjs b/packages/remix/rollup.npm.config.mjs
index 4b2b0d1223f1..79803c84f486 100644
--- a/packages/remix/rollup.npm.config.mjs
+++ b/packages/remix/rollup.npm.config.mjs
@@ -13,5 +13,5 @@ export default [
       },
     }),
   ),
-  makeOtelLoader('./build/register.mjs'),
+  makeOtelLoader('./build/register.mjs', 'sentry-node'),
 ];

From a5ae9a16bce6cd45ec7ca41aab4b39b600faddcc Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Tue, 2 Apr 2024 07:17:39 +0000
Subject: [PATCH 6/8] Add disable test to ci

---
 .github/workflows/build.yml | 1 +
 1 file changed, 1 insertion(+)

diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
index ca5452280d7c..a017b3d7add1 100644
--- a/.github/workflows/build.yml
+++ b/.github/workflows/build.yml
@@ -1037,6 +1037,7 @@ jobs:
             'create-remix-app-v2',
             'create-remix-app-express-vite-dev',
             'debug-id-sourcemaps',
+            # 'esm-loader-node-express-app', # This is currently broken for upstream reasons. See https://github.com/getsentry/sentry-javascript/pull/11338#issuecomment-2025450675
             'nextjs-app-dir',
             'nextjs-14',
             'react-create-hash-router',

From 9236a80dd49896bf3b117e4cf1affce65b59076c Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Tue, 2 Apr 2024 10:05:20 +0000
Subject: [PATCH 7/8] Use `register`

---
 .../esm-loader-node-express-app/package.json                  | 4 ++--
 dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js       | 4 ++--
 dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js | 3 +--
 dev-packages/rollup-utils/npmHelpers.mjs                      | 2 +-
 4 files changed, 6 insertions(+), 7 deletions(-)

diff --git a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json
index 99dfd693a272..8ed10b0e6c58 100644
--- a/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json
+++ b/dev-packages/e2e-tests/test-applications/esm-loader-node-express-app/package.json
@@ -3,7 +3,7 @@
   "version": "1.0.0",
   "private": true,
   "scripts": {
-    "start": "node --loader=@sentry/node/register src/app.mjs",
+    "start": "node --import=@sentry/node/register src/app.mjs",
     "clean": "npx rimraf node_modules,pnpm-lock.yaml",
     "test:build": "pnpm install",
     "test:assert": "playwright test"
@@ -22,6 +22,6 @@
   },
   "volta": {
     "extends": "../../package.json",
-    "node": "18.18.2"
+    "node": "18.19.1"
   }
 }
diff --git a/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js b/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
index 117b7ad92cc0..99c312a20ab4 100644
--- a/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
+++ b/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
@@ -1,2 +1,2 @@
-import { getFormat, getSource, load, resolve } from '@opentelemetry/instrumentation/hook.mjs';
-export { load, resolve, getFormat, getSource };
+import { register } from 'module';
+register('@opentelemetry/instrumentation/hook.mjs', import.meta.url);
diff --git a/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js b/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
index 86c4b731472e..bb3f3084cbed 100644
--- a/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
+++ b/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
@@ -1,2 +1 @@
-import { getFormat, getSource, load, resolve } from '@sentry/node/register';
-export { load, resolve, getFormat, getSource };
+import '@sentry/node/register';
diff --git a/dev-packages/rollup-utils/npmHelpers.mjs b/dev-packages/rollup-utils/npmHelpers.mjs
index 20cd096efdfa..bbd63e4ec621 100644
--- a/dev-packages/rollup-utils/npmHelpers.mjs
+++ b/dev-packages/rollup-utils/npmHelpers.mjs
@@ -148,7 +148,7 @@ export function makeNPMConfigVariants(baseConfig, options = {}) {
 
 /**
  * This creates a loader file at the target location as part of the rollup build.
- * This loader script can then be used in combination with various Node.js flags (like --loader=...) to monkeypatch 3rd party modules.
+ * This loader script can then be used in combination with various Node.js flags (like --import=...) to monkeypatch 3rd party modules.
  */
 export function makeOtelLoader(outputPath, hookVariant) {
   if (hookVariant !== 'otel' && hookVariant !== 'sentry-node') {

From ab9ddc80d1679d410957234afb497507d3faf538 Mon Sep 17 00:00:00 2001
From: Luca Forstner <luca.forstner@sentry.io>
Date: Wed, 3 Apr 2024 09:37:28 +0000
Subject: [PATCH 8/8] Add secondary `hook` to support the --loader usecase

---
 .../code/otelEsmHooksLoaderTemplate.js        |  2 +
 ...te.js => otelEsmRegisterLoaderTemplate.js} |  0
 .../code/sentryNodeEsmHooksLoaderTemplate.js  |  1 +
 .../code/sentryNodeEsmLoaderTemplate.js       |  1 -
 .../sentryNodeEsmRegisterLoaderTemplate.js    |  2 +
 dev-packages/rollup-utils/npmHelpers.mjs      | 61 +++++++++++++------
 packages/astro/package.json                   |  7 ++-
 packages/astro/rollup.npm.config.mjs          |  4 +-
 packages/aws-serverless/package.json          |  7 ++-
 packages/aws-serverless/rollup.npm.config.mjs |  4 +-
 packages/google-cloud-serverless/package.json |  7 ++-
 .../rollup.npm.config.mjs                     |  4 +-
 packages/nextjs/package.json                  |  7 ++-
 packages/nextjs/rollup.npm.config.mjs         |  4 +-
 packages/node/package.json                    |  7 ++-
 packages/node/rollup.npm.config.mjs           |  4 +-
 packages/remix/package.json                   |  7 ++-
 packages/remix/rollup.npm.config.mjs          |  4 +-
 18 files changed, 97 insertions(+), 36 deletions(-)
 create mode 100644 dev-packages/rollup-utils/code/otelEsmHooksLoaderTemplate.js
 rename dev-packages/rollup-utils/code/{otelEsmLoaderTemplate.js => otelEsmRegisterLoaderTemplate.js} (100%)
 create mode 100644 dev-packages/rollup-utils/code/sentryNodeEsmHooksLoaderTemplate.js
 delete mode 100644 dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
 create mode 100644 dev-packages/rollup-utils/code/sentryNodeEsmRegisterLoaderTemplate.js

diff --git a/dev-packages/rollup-utils/code/otelEsmHooksLoaderTemplate.js b/dev-packages/rollup-utils/code/otelEsmHooksLoaderTemplate.js
new file mode 100644
index 000000000000..51c72d9d7192
--- /dev/null
+++ b/dev-packages/rollup-utils/code/otelEsmHooksLoaderTemplate.js
@@ -0,0 +1,2 @@
+import { getFormat, getSource, load, resolve } from '@opentelemetry/instrumentation/hook.mjs';
+export { getFormat, getSource, load, resolve };
diff --git a/dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js b/dev-packages/rollup-utils/code/otelEsmRegisterLoaderTemplate.js
similarity index 100%
rename from dev-packages/rollup-utils/code/otelEsmLoaderTemplate.js
rename to dev-packages/rollup-utils/code/otelEsmRegisterLoaderTemplate.js
diff --git a/dev-packages/rollup-utils/code/sentryNodeEsmHooksLoaderTemplate.js b/dev-packages/rollup-utils/code/sentryNodeEsmHooksLoaderTemplate.js
new file mode 100644
index 000000000000..06fb71a76860
--- /dev/null
+++ b/dev-packages/rollup-utils/code/sentryNodeEsmHooksLoaderTemplate.js
@@ -0,0 +1 @@
+import '@sentry/node/hook';
diff --git a/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js b/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
deleted file mode 100644
index bb3f3084cbed..000000000000
--- a/dev-packages/rollup-utils/code/sentryNodeEsmLoaderTemplate.js
+++ /dev/null
@@ -1 +0,0 @@
-import '@sentry/node/register';
diff --git a/dev-packages/rollup-utils/code/sentryNodeEsmRegisterLoaderTemplate.js b/dev-packages/rollup-utils/code/sentryNodeEsmRegisterLoaderTemplate.js
new file mode 100644
index 000000000000..5a9fa441f106
--- /dev/null
+++ b/dev-packages/rollup-utils/code/sentryNodeEsmRegisterLoaderTemplate.js
@@ -0,0 +1,2 @@
+import { getFormat, getSource, load, resolve } from '@sentry/node/register';
+export { getFormat, getSource, load, resolve };
diff --git a/dev-packages/rollup-utils/npmHelpers.mjs b/dev-packages/rollup-utils/npmHelpers.mjs
index bbd63e4ec621..fa64ecbdb1d1 100644
--- a/dev-packages/rollup-utils/npmHelpers.mjs
+++ b/dev-packages/rollup-utils/npmHelpers.mjs
@@ -150,17 +150,28 @@ export function makeNPMConfigVariants(baseConfig, options = {}) {
  * This creates a loader file at the target location as part of the rollup build.
  * This loader script can then be used in combination with various Node.js flags (like --import=...) to monkeypatch 3rd party modules.
  */
-export function makeOtelLoader(outputPath, hookVariant) {
+export function makeOtelLoaders(outputFolder, hookVariant) {
   if (hookVariant !== 'otel' && hookVariant !== 'sentry-node') {
     throw new Error('hookVariant is neither "otel" nor "sentry-node". Pick one.');
   }
 
-  const foundLoaderExport = Object.keys(packageDotJSON.exports ?? {}).some(key => {
-    return packageDotJSON?.exports?.[key]?.import?.default === outputPath;
+  const expectedRegisterLoaderLocation = `${outputFolder}/register.mjs`;
+  const foundRegisterLoaderExport = Object.keys(packageDotJSON.exports ?? {}).some(key => {
+    return packageDotJSON?.exports?.[key]?.import?.default === expectedRegisterLoaderLocation;
   });
-  if (!foundLoaderExport) {
+  if (!foundRegisterLoaderExport) {
     throw new Error(
-      `You used the makeOtelLoader() rollup utility without specifying the loader inside \`exports[something].import.default\`. Please add "${outputPath}" as a value there (maybe check for typos - it needs to be "${outputPath}" exactly).`,
+      `You used the makeOtelLoaders() rollup utility without specifying the register loader inside \`exports[something].import.default\`. Please add "${expectedRegisterLoaderLocation}" as a value there (maybe check for typos - it needs to be "${expectedRegisterLoaderLocation}" exactly).`,
+    );
+  }
+
+  const expectedHooksLoaderLocation = `${outputFolder}/hook.mjs`;
+  const foundHookLoaderExport = Object.keys(packageDotJSON.exports ?? {}).some(key => {
+    return packageDotJSON?.exports?.[key]?.import?.default === expectedHooksLoaderLocation;
+  });
+  if (!foundHookLoaderExport) {
+    throw new Error(
+      `You used the makeOtelLoaders() rollup utility without specifying the hook loader inside \`exports[something].import.default\`. Please add "${expectedHooksLoaderLocation}" as a value there (maybe check for typos - it needs to be "${expectedHooksLoaderLocation}" exactly).`,
     );
   }
 
@@ -170,23 +181,39 @@ export function makeOtelLoader(outputPath, hookVariant) {
   });
   if (!foundImportInTheMiddleDep) {
     throw new Error(
-      `You used the makeOtelLoader() rollup utility but didn't specify the "${requiredDep}" dependency in ${path.resolve(
+      `You used the makeOtelLoaders() rollup utility but didn't specify the "${requiredDep}" dependency in ${path.resolve(
         process.cwd(),
         'package.json',
       )}. Please add it to the dependencies.`,
     );
   }
 
-  return defineConfig({
-    input: path.join(
-      __dirname,
-      'code',
-      hookVariant === 'otel' ? 'otelEsmLoaderTemplate.js' : 'sentryNodeEsmLoaderTemplate.js',
-    ),
-    external: ['@opentelemetry/instrumentation/hook.mjs', '@sentry/node/register'],
-    output: {
-      format: 'esm',
-      file: outputPath,
+  return defineConfig([
+    // register() hook
+    {
+      input: path.join(
+        __dirname,
+        'code',
+        hookVariant === 'otel' ? 'otelEsmRegisterLoaderTemplate.js' : 'sentryNodeEsmRegisterLoaderTemplate.js',
+      ),
+      external: ['@opentelemetry/instrumentation/hook.mjs', '@sentry/node/register'],
+      output: {
+        format: 'esm',
+        file: path.join(outputFolder, 'register.mjs'),
+      },
     },
-  });
+    // --loader hook
+    {
+      input: path.join(
+        __dirname,
+        'code',
+        hookVariant === 'otel' ? 'otelEsmHooksLoaderTemplate.js' : 'sentryNodeEsmHooksLoaderTemplate.js',
+      ),
+      external: ['@opentelemetry/instrumentation/hook.mjs', '@sentry/node/hook'],
+      output: {
+        format: 'esm',
+        file: path.join(outputFolder, 'hook.mjs'),
+      },
+    },
+  ]);
 }
diff --git a/packages/astro/package.json b/packages/astro/package.json
index 233b5a903701..ecdfa6fc06a7 100644
--- a/packages/astro/package.json
+++ b/packages/astro/package.json
@@ -46,7 +46,12 @@
       "import": {
         "default": "./build/register.mjs"
       }
-    }
+    },
+"./hook": {
+      "import": {
+        "default": "./build/hook.mjs"
+      }
+}
   },
   "publishConfig": {
     "access": "public"
diff --git a/packages/astro/rollup.npm.config.mjs b/packages/astro/rollup.npm.config.mjs
index b5987be16a8c..ca3b338433a7 100644
--- a/packages/astro/rollup.npm.config.mjs
+++ b/packages/astro/rollup.npm.config.mjs
@@ -1,4 +1,4 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoaders } from '@sentry-internal/rollup-utils';
 
 const variants = makeNPMConfigVariants(
   makeBaseNPMConfig({
@@ -14,4 +14,4 @@ const variants = makeNPMConfigVariants(
   }),
 );
 
-export default [...variants, makeOtelLoader('./build/register.mjs', 'sentry-node')];
+export default [...variants, ...makeOtelLoaders('./build', 'sentry-node')];
diff --git a/packages/aws-serverless/package.json b/packages/aws-serverless/package.json
index 536c12d1894d..7109d496c13a 100644
--- a/packages/aws-serverless/package.json
+++ b/packages/aws-serverless/package.json
@@ -29,7 +29,12 @@
       "import": {
         "default": "./build/register.mjs"
       }
-    }
+    },
+"./hook": {
+      "import": {
+        "default": "./build/hook.mjs"
+      }
+}
   },
   "typesVersions": {
     "<4.9": {
diff --git a/packages/aws-serverless/rollup.npm.config.mjs b/packages/aws-serverless/rollup.npm.config.mjs
index 67ed35f11ab6..59af857e3c0a 100644
--- a/packages/aws-serverless/rollup.npm.config.mjs
+++ b/packages/aws-serverless/rollup.npm.config.mjs
@@ -1,4 +1,4 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoaders } from '@sentry-internal/rollup-utils';
 
 export default [
   ...makeNPMConfigVariants(
@@ -12,5 +12,5 @@ export default [
     }),
     { emitEsm: false },
   ),
-  makeOtelLoader('./build/register.mjs', 'sentry-node'),
+  ...makeOtelLoaders('./build', 'sentry-node'),
 ];
diff --git a/packages/google-cloud-serverless/package.json b/packages/google-cloud-serverless/package.json
index 234a72ed1f36..0519c5efae32 100644
--- a/packages/google-cloud-serverless/package.json
+++ b/packages/google-cloud-serverless/package.json
@@ -30,7 +30,12 @@
       "import": {
         "default": "./build/register.mjs"
       }
-    }
+    },
+"./hook": {
+      "import": {
+        "default": "./build/hook.mjs"
+      }
+}
   },
   "typesVersions": {
     "<4.9": {
diff --git a/packages/google-cloud-serverless/rollup.npm.config.mjs b/packages/google-cloud-serverless/rollup.npm.config.mjs
index 4d511654b3b1..5e0b74554d96 100644
--- a/packages/google-cloud-serverless/rollup.npm.config.mjs
+++ b/packages/google-cloud-serverless/rollup.npm.config.mjs
@@ -1,3 +1,3 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoaders } from '@sentry-internal/rollup-utils';
 
-export default [...makeNPMConfigVariants(makeBaseNPMConfig()), makeOtelLoader('./build/register.mjs', 'sentry-node')];
+export default [...makeNPMConfigVariants(makeBaseNPMConfig()), ...makeOtelLoaders('./build', 'sentry-node')];
diff --git a/packages/nextjs/package.json b/packages/nextjs/package.json
index 02f09cf98743..1dbb1509b55c 100644
--- a/packages/nextjs/package.json
+++ b/packages/nextjs/package.json
@@ -27,7 +27,12 @@
       "import": {
         "default": "./build/register.mjs"
       }
-    }
+    },
+"./hook": {
+      "import": {
+        "default": "./build/hook.mjs"
+      }
+}
   },
   "typesVersions": {
     "<4.9": {
diff --git a/packages/nextjs/rollup.npm.config.mjs b/packages/nextjs/rollup.npm.config.mjs
index 96931b8f8afb..afe41659238f 100644
--- a/packages/nextjs/rollup.npm.config.mjs
+++ b/packages/nextjs/rollup.npm.config.mjs
@@ -1,4 +1,4 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoaders } from '@sentry-internal/rollup-utils';
 
 export default [
   ...makeNPMConfigVariants(
@@ -72,5 +72,5 @@ export default [
       },
     }),
   ),
-  makeOtelLoader('./build/register.mjs', 'sentry-node'),
+  ...makeOtelLoaders('./build', 'sentry-node'),
 ];
diff --git a/packages/node/package.json b/packages/node/package.json
index d7b0dc38fba3..938dd837ad81 100644
--- a/packages/node/package.json
+++ b/packages/node/package.json
@@ -35,7 +35,12 @@
       "import": {
         "default": "./build/register.mjs"
       }
-    }
+    },
+"./hook": {
+      "import": {
+        "default": "./build/hook.mjs"
+      }
+}
   },
   "typesVersions": {
     "<4.9": {
diff --git a/packages/node/rollup.npm.config.mjs b/packages/node/rollup.npm.config.mjs
index 8e28541d64a9..443661d2882a 100644
--- a/packages/node/rollup.npm.config.mjs
+++ b/packages/node/rollup.npm.config.mjs
@@ -1,11 +1,11 @@
 import replace from '@rollup/plugin-replace';
-import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoaders } from '@sentry-internal/rollup-utils';
 import { createAnrWorkerCode } from './rollup.anr-worker.config.mjs';
 
 const { workerRollupConfig, getBase64Code } = createAnrWorkerCode();
 
 export default [
-  makeOtelLoader('./build/register.mjs', 'otel'),
+  ...makeOtelLoaders('./build', 'otel'),
   // The worker needs to be built first since it's output is used in the main bundle.
   workerRollupConfig,
   ...makeNPMConfigVariants(
diff --git a/packages/remix/package.json b/packages/remix/package.json
index bf2975485561..9d8d4b80f294 100644
--- a/packages/remix/package.json
+++ b/packages/remix/package.json
@@ -38,7 +38,12 @@
       "import": {
         "default": "./build/register.mjs"
       }
-    }
+    },
+"./hook": {
+      "import": {
+        "default": "./build/hook.mjs"
+      }
+}
   },
   "typesVersions": {
     "<4.9": {
diff --git a/packages/remix/rollup.npm.config.mjs b/packages/remix/rollup.npm.config.mjs
index 79803c84f486..b705fba0c55f 100644
--- a/packages/remix/rollup.npm.config.mjs
+++ b/packages/remix/rollup.npm.config.mjs
@@ -1,4 +1,4 @@
-import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoader } from '@sentry-internal/rollup-utils';
+import { makeBaseNPMConfig, makeNPMConfigVariants, makeOtelLoaders } from '@sentry-internal/rollup-utils';
 
 export default [
   ...makeNPMConfigVariants(
@@ -13,5 +13,5 @@ export default [
       },
     }),
   ),
-  makeOtelLoader('./build/register.mjs', 'sentry-node'),
+  ...makeOtelLoaders('./build', 'sentry-node'),
 ];