diff --git a/packages/aws-cdk/jest.config.js b/packages/aws-cdk/jest.config.js
index 292f68b459252..ae3fb7ad49a8d 100644
--- a/packages/aws-cdk/jest.config.js
+++ b/packages/aws-cdk/jest.config.js
@@ -7,4 +7,7 @@ module.exports = {
             branches: 45,
         },
     },
+
+    // We have many tests here that commonly time out
+    testTimeout: 30_000,
 };
diff --git a/packages/aws-cdk/lib/cdk-toolkit.ts b/packages/aws-cdk/lib/cdk-toolkit.ts
index 9304758e28030..320cb82d45128 100644
--- a/packages/aws-cdk/lib/cdk-toolkit.ts
+++ b/packages/aws-cdk/lib/cdk-toolkit.ts
@@ -69,6 +69,24 @@ export interface CdkToolkitProps {
   sdkProvider: SdkProvider;
 }
 
+/**
+ * When to build assets
+ */
+export enum AssetBuildTime {
+  /**
+   * Build all assets before deploying the first stack
+   *
+   * This is intended for expensive Docker image builds; so that if the Docker image build
+   * fails, no stacks are unnecessarily deployed (with the attendant wait time).
+   */
+  ALL_BEFORE_DEPLOY,
+
+  /**
+   * Build assets just-in-time, before publishing
+   */
+  JUST_IN_TIME,
+};
+
 /**
  * Toolkit logic
  *
@@ -167,17 +185,22 @@ export class CdkToolkit {
     }
 
     const stacks = stackCollection.stackArtifacts;
+    const assetBuildTime = options.assetBuildTime ?? AssetBuildTime.ALL_BEFORE_DEPLOY;
+
 
     const stackOutputs: { [key: string]: any } = { };
     const outputsFile = options.outputsFile;
 
-    try {
-      await buildAllStackAssets(stackCollection.stackArtifacts, {
-        buildStackAssets: (a) => this.buildAllAssetsForSingleStack(a, options),
-      });
-    } catch (e) {
-      error('\n ❌ Building assets failed: %s', e);
-      throw e;
+    if (assetBuildTime === AssetBuildTime.ALL_BEFORE_DEPLOY) {
+      // Prebuild all assets
+      try {
+        await buildAllStackAssets(stackCollection.stackArtifacts, {
+          buildStackAssets: (a) => this.buildAllAssetsForSingleStack(a, options),
+        });
+      } catch (e) {
+        error('\n ❌ Building assets failed: %s', e);
+        throw e;
+      }
     }
 
     const deployStack = async (stack: cxapi.CloudFormationStackArtifact) => {
@@ -257,7 +280,7 @@ export class CdkToolkit {
           rollback: options.rollback,
           hotswap: options.hotswap,
           extraUserAgent: options.extraUserAgent,
-          buildAssets: false,
+          buildAssets: assetBuildTime !== AssetBuildTime.ALL_BEFORE_DEPLOY,
           assetParallelism: options.assetParallelism,
         });
 
@@ -1042,6 +1065,15 @@ export interface DeployOptions extends CfnDeployOptions, WatchOptions {
    * @default true
    */
   readonly assetParallelism?: boolean;
+
+  /**
+   * When to build assets
+   *
+   * The default is the Docker-friendly default.
+   *
+   * @default AssetBuildTime.ALL_BEFORE_DEPLOY
+   */
+  readonly assetBuildTime?: AssetBuildTime;
 }
 
 export interface ImportOptions extends CfnDeployOptions {
@@ -1136,4 +1168,4 @@ function roundPercentage(num: number): number {
  */
 function millisecondsToSeconds(num: number): number {
   return num / 1000;
-}
+}
\ No newline at end of file
diff --git a/packages/aws-cdk/lib/cli.ts b/packages/aws-cdk/lib/cli.ts
index 516e6d30f20dd..4192c795689cb 100644
--- a/packages/aws-cdk/lib/cli.ts
+++ b/packages/aws-cdk/lib/cli.ts
@@ -13,7 +13,7 @@ import { execProgram } from '../lib/api/cxapp/exec';
 import { PluginHost } from '../lib/api/plugin';
 import { ToolkitInfo } from '../lib/api/toolkit-info';
 import { StackActivityProgress } from '../lib/api/util/cloudformation/stack-activity-monitor';
-import { CdkToolkit } from '../lib/cdk-toolkit';
+import { CdkToolkit, AssetBuildTime } from '../lib/cdk-toolkit';
 import { realHandler as context } from '../lib/commands/context';
 import { realHandler as docs } from '../lib/commands/docs';
 import { realHandler as doctor } from '../lib/commands/doctor';
@@ -157,7 +157,8 @@ async function parseCommandLineArguments() {
           "Only in effect if specified alongside the '--watch' option",
       })
       .option('concurrency', { type: 'number', desc: 'Maximum number of simultaneous deployments (dependency permitting) to execute.', default: 1, requiresArg: true })
-      .option('asset-parallelism', { type: 'boolean', desc: 'Whether to build/publish assets in parallel' }),
+      .option('asset-parallelism', { type: 'boolean', desc: 'Whether to build/publish assets in parallel' })
+      .option('asset-prebuild', { type: 'boolean', desc: 'Whether to build all assets before deploying the first stack (useful for failing Docker builds)', default: true }),
     )
     .command('import [STACK]', 'Import existing resource(s) into the given STACK', (yargs: Argv) => yargs
       .option('execute', { type: 'boolean', desc: 'Whether to execute ChangeSet (--no-execute will NOT execute the ChangeSet)', default: true })
@@ -521,6 +522,7 @@ async function initCommandLine() {
           traceLogs: args.logs,
           concurrency: args.concurrency,
           assetParallelism: configuration.settings.get(['assetParallelism']),
+          assetBuildTime: configuration.settings.get(['assetPrebuild']) ? AssetBuildTime.ALL_BEFORE_DEPLOY : AssetBuildTime.JUST_IN_TIME,
         });
 
       case 'import':
diff --git a/packages/aws-cdk/lib/settings.ts b/packages/aws-cdk/lib/settings.ts
index b4e3a2f4ebf7d..e6505d829c1af 100644
--- a/packages/aws-cdk/lib/settings.ts
+++ b/packages/aws-cdk/lib/settings.ts
@@ -290,6 +290,7 @@ export class Settings {
       rollback: argv.rollback,
       notices: argv.notices,
       assetParallelism: argv['asset-parallelism'],
+      assetPrebuild: argv['asset-prebuild'],
     });
   }
 
diff --git a/packages/aws-cdk/test/cdk-toolkit.test.ts b/packages/aws-cdk/test/cdk-toolkit.test.ts
index 205eb8b28910a..d2a8000464281 100644
--- a/packages/aws-cdk/test/cdk-toolkit.test.ts
+++ b/packages/aws-cdk/test/cdk-toolkit.test.ts
@@ -62,7 +62,7 @@ import { Bootstrapper } from '../lib/api/bootstrap';
 import { CloudFormationDeployments, DeployStackOptions, DestroyStackOptions } from '../lib/api/cloudformation-deployments';
 import { DeployStackResult } from '../lib/api/deploy-stack';
 import { Template } from '../lib/api/util/cloudformation';
-import { CdkToolkit, Tag } from '../lib/cdk-toolkit';
+import { CdkToolkit, Tag, AssetBuildTime } from '../lib/cdk-toolkit';
 import { RequireApproval } from '../lib/diff';
 import { flatten } from '../lib/util';
 import { instanceMockFrom, MockCloudExecutable, TestStackArtifact, withMocked } from './util';
@@ -589,6 +589,32 @@ describe('deploy', () => {
         }));
       });
     });
+
+    test('can disable asset prebuild', async () => {
+      // GIVEN
+      cloudExecutable = new MockCloudExecutable({
+        stacks: [MockStack.MOCK_STACK_WITH_ASSET],
+      });
+      const fakeCloudFormation = new FakeCloudFormation({});
+
+      const toolkit = new CdkToolkit({
+        cloudExecutable,
+        configuration: cloudExecutable.configuration,
+        sdkProvider: cloudExecutable.sdkProvider,
+        cloudFormation: fakeCloudFormation,
+      });
+
+      // WHEN
+      // Not the best test but following this through to the asset publishing library fails
+      await withMocked(fakeCloudFormation, 'buildStackAssets', async (mockBuildStackAssets) => {
+        await toolkit.deploy({
+          selector: { patterns: ['Test-Stack-Asset'] },
+          assetBuildTime: AssetBuildTime.JUST_IN_TIME,
+        });
+
+        expect(mockBuildStackAssets).not.toHaveBeenCalled();
+      });
+    });
   });
 });