diff --git a/packages/@aws-cdk/core/lib/private/asset-staging.ts b/packages/@aws-cdk/core/lib/private/asset-staging.ts
index 27cfbfc604152..9f6e6b89e2452 100644
--- a/packages/@aws-cdk/core/lib/private/asset-staging.ts
+++ b/packages/@aws-cdk/core/lib/private/asset-staging.ts
@@ -199,6 +199,7 @@ export class AssetBundlingVolumeCopy extends AssetBundlingBase {
 export function dockerExec(args: string[], options?: SpawnSyncOptions) {
   const prog = process.env.CDK_DOCKER ?? 'docker';
   const proc = spawnSync(prog, args, options ?? {
+    encoding: 'utf-8',
     stdio: [ // show Docker output
       'ignore', // ignore stdio
       process.stderr, // redirect stdout to stderr
@@ -211,10 +212,25 @@ export function dockerExec(args: string[], options?: SpawnSyncOptions) {
   }
 
   if (proc.status !== 0) {
-    if (proc.stdout || proc.stderr) {
-      throw new Error(`[Status ${proc.status}] stdout: ${proc.stdout?.toString().trim()}\n\n\nstderr: ${proc.stderr?.toString().trim()}`);
+    const reason = proc.signal != null
+      ? `signal ${proc.signal}`
+      : `status ${proc.status}`;
+    const command = [prog, ...args.map((arg) => /[^a-z0-9_-]/i.test(arg) ? JSON.stringify(arg) : arg)].join(' ');
+
+    function prependLines(firstLine: string, text: Buffer | string | undefined): string[] {
+      if (!text || text.length === 0) {
+        return [];
+      }
+      const padding = ' '.repeat(firstLine.length);
+      return text.toString('utf-8').split('\n').map((line, idx) => `${idx === 0 ? firstLine : padding}${line}`);
     }
-    throw new Error(`${prog} exited with status ${proc.status}`);
+
+    throw new Error([
+      `${prog} exited with ${reason}`,
+      ...prependLines('--> STDOUT:  ', proc.stdout ) ?? [],
+      ...prependLines('--> STDERR:  ', proc.stderr ) ?? [],
+      `--> Command: ${command}`,
+    ].join('\n'));
   }
 
   return proc;
diff --git a/packages/@aws-cdk/core/test/bundling.test.ts b/packages/@aws-cdk/core/test/bundling.test.ts
index fe2e0cea608f7..4fa1a29c49d89 100644
--- a/packages/@aws-cdk/core/test/bundling.test.ts
+++ b/packages/@aws-cdk/core/test/bundling.test.ts
@@ -44,7 +44,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('bundling with image from asset', () => {
@@ -188,7 +188,7 @@ describe('bundling', () => {
     });
 
     const image = DockerImage.fromRegistry('alpine');
-    expect(() => image.run()).toThrow(/\[Status -1\]/);
+    expect(() => image.run()).toThrow(/exited with status -1/);
   });
 
   test('BundlerDockerImage json is the bundler image name by default', () => {
@@ -294,7 +294,7 @@ describe('bundling', () => {
       'alpine',
       '--cool-entrypoint-arg',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('cp utility copies from an image', () => {
@@ -404,7 +404,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('adding user provided network options', () => {
@@ -437,7 +437,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('adding user provided docker volume options', () => {
@@ -475,7 +475,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('ensure selinux docker mount', () => {
@@ -516,7 +516,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('ensure selinux docker mount on linux with selinux disabled', () => {
@@ -557,7 +557,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('ensure no selinux docker mount if selinuxenabled isn\'t an available command', () => {
@@ -598,7 +598,7 @@ describe('bundling', () => {
       '-w', '/working-directory',
       'alpine',
       'cool', 'command',
-    ], { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ], { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 
   test('ensure correct Docker CLI arguments are returned', () => {
diff --git a/packages/@aws-cdk/core/test/private/asset-staging.test.ts b/packages/@aws-cdk/core/test/private/asset-staging.test.ts
index adcbf71ffe5d9..4d29406552dfc 100644
--- a/packages/@aws-cdk/core/test/private/asset-staging.test.ts
+++ b/packages/@aws-cdk/core/test/private/asset-staging.test.ts
@@ -33,20 +33,20 @@ describe('bundling', () => {
     // volume Creation
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'volume', 'create', sinon.match(/assetInput.*/g),
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'volume', 'create', sinon.match(/assetOutput.*/g),
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     // volume removal
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'volume', 'rm', sinon.match(/assetInput.*/g),
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'volume', 'rm', sinon.match(/assetOutput.*/g),
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     // prepare copy container
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
@@ -58,29 +58,29 @@ describe('bundling', () => {
       'sh',
       '-c',
       `mkdir -p ${AssetStaging.BUNDLING_INPUT_DIR} && chown -R ${options.user} ${AssetStaging.BUNDLING_OUTPUT_DIR} && chown -R ${options.user} ${AssetStaging.BUNDLING_INPUT_DIR}`,
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     // delete copy container
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'rm', sinon.match(/copyContainer.*/g),
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     // copy files to copy container
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'cp', `${options.sourcePath}/.`, `${helper.copyContainerName}:${AssetStaging.BUNDLING_INPUT_DIR}`,
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     // copy files from copy container to host
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match([
       'cp', `${helper.copyContainerName}:${AssetStaging.BUNDLING_OUTPUT_DIR}/.`, options.bundleDir,
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
     // actual docker run
     expect(spawnSyncStub.calledWith(DOCKER_CMD, sinon.match.array.contains([
       'run', '--rm',
       '--volumes-from', helper.copyContainerName,
       'alpine',
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
 
   });
 
@@ -109,6 +109,6 @@ describe('bundling', () => {
       'run', '--rm',
       '-v',
       'alpine',
-    ]), { stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
+    ]), { encoding: 'utf-8', stdio: ['ignore', process.stderr, 'inherit'] })).toEqual(true);
   });
 });