diff --git a/packages/aws-cdk-lib/core/lib/private/asset-staging.ts b/packages/aws-cdk-lib/core/lib/private/asset-staging.ts
index 0113f4c0f0e77..e388802b2342a 100644
--- a/packages/aws-cdk-lib/core/lib/private/asset-staging.ts
+++ b/packages/aws-cdk-lib/core/lib/private/asset-staging.ts
@@ -214,6 +214,15 @@ export function dockerExec(args: string[], options?: SpawnSyncOptions) {
   });
 
   if (proc.error) {
+    if ((proc.error as NodeJS.ErrnoException).code === 'ENOENT') {
+      throw new ExecutionError(
+        lit`DockerNotFound`,
+        `Failed to run bundling with Docker: ${prog} is not installed or not in PATH. ` +
+        'If you are bundling a Lambda function, consider installing esbuild locally ' +
+        '(npm install --save-dev esbuild) to avoid Docker entirely. ' +
+        `Otherwise, install Docker and make sure "${prog}" is available on your PATH.`,
+      );
+    }
     throw proc.error;
   }
 
diff --git a/packages/aws-cdk-lib/core/test/private/asset-staging.test.ts b/packages/aws-cdk-lib/core/test/private/asset-staging.test.ts
index c275e0370f5e9..5c99b92150de9 100644
--- a/packages/aws-cdk-lib/core/test/private/asset-staging.test.ts
+++ b/packages/aws-cdk-lib/core/test/private/asset-staging.test.ts
@@ -1,7 +1,7 @@
 import * as child_process from 'child_process';
 import * as sinon from 'sinon';
 import { AssetStaging, DockerImage } from '../../lib';
-import { AssetBundlingBindMount, AssetBundlingVolumeCopy } from '../../lib/private/asset-staging';
+import { AssetBundlingBindMount, AssetBundlingVolumeCopy, dockerExec } from '../../lib/private/asset-staging';
 
 const DOCKER_CMD = process.env.CDK_DOCKER ?? 'docker';
 
@@ -85,6 +85,28 @@ describe('bundling', () => {
     ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
+  test('dockerExec throws a helpful error when docker is not found (ENOENT)', () => {
+    const enoentError = new Error('spawnSync docker ENOENT') as NodeJS.ErrnoException;
+    enoentError.code = 'ENOENT';
+
+    sinon.stub(child_process, 'spawnSync').returns({
+      status: null,
+      stderr: Buffer.from(''),
+      stdout: Buffer.from(''),
+      pid: 0,
+      output: [],
+      signal: null,
+      error: enoentError,
+    });
+
+    expect(() => dockerExec(['run', 'hello'])).toThrow(
+      /docker is not installed or not in PATH/,
+    );
+    expect(() => dockerExec(['run', 'hello'])).toThrow(
+      /consider installing esbuild/,
+    );
+  });
+
   test('AssetBundlingBindMount bundles with bind mount ', () => {
     // GIVEN
     sinon.stub(process, 'platform').value('darwin');