diff --git a/packages/aws-cdk-lib/package.json b/packages/aws-cdk-lib/package.json
index 296f1cae8dd46..1661c92b1e3c6 100644
--- a/packages/aws-cdk-lib/package.json
+++ b/packages/aws-cdk-lib/package.json
@@ -31,6 +31,7 @@
     "stripDeprecated": true,
     "compressAssembly": true,
     "pre": [
+      "ts-node ./scripts/strip-nested-bundled-deps.ts",
       "ts-node region-info/build-tools/generate-static-data.ts",
       "(rm -rf core/test/fs/fixtures && cd core/test/fs && tar -xzf fixtures.tar.gz)",
       "(rm -rf assets/test/fs/fixtures && cd assets/test/fs && tar -xzf fixtures.tar.gz)",
diff --git a/packages/aws-cdk-lib/scripts/strip-nested-bundled-deps.ts b/packages/aws-cdk-lib/scripts/strip-nested-bundled-deps.ts
new file mode 100644
index 0000000000000..2e7532a4431bd
--- /dev/null
+++ b/packages/aws-cdk-lib/scripts/strip-nested-bundled-deps.ts
@@ -0,0 +1,31 @@
+#!/usr/bin/env node
+/**
+ * Node.js fully doesn't survive if the same dependency is bundled at multiple
+ * levels. Since we bundle `@aws-cdk/cloud-assembly-api` and that package
+ * bundles some dependencies that `aws-cdk-lib` also bundles, we tickle that
+ * bug.
+ *
+ * Get rid of that problem by deleting all bundled dependencies from deeper
+ * `node_modules` directories that we already bundle ourselves as well.
+ *
+ * We can run this command either before compilation or before packing. We choose
+ * to run it as early as possible to improve the chances of us detecting any
+ * problems with it.
+ */
+import * as fs from 'fs';
+
+function main() {
+  const pj = JSON.parse(fs.readFileSync('package.json', 'utf-8'));
+  const bundledDeps = pj.bundleDependencies as string[];
+
+  // A bundled dependency cannot be bundled under any other bundled depencency.
+  for (const outerDep of bundledDeps) {
+    for (const unwantedDep of bundledDeps) {
+      const conflictPath = `node_modules/${outerDep}/node_modules/${unwantedDep}`;
+      // { force: true } will make this not error if the path doesn't exist.
+      fs.rmSync(conflictPath, { recursive: true, force: true });
+    }
+  }
+}
+
+main();