diff --git a/packages/@aws-cdk/core/lib/asset-staging.ts b/packages/@aws-cdk/core/lib/asset-staging.ts
index 5ecafd9d3da56..ee1f2bafc6a04 100644
--- a/packages/@aws-cdk/core/lib/asset-staging.ts
+++ b/packages/@aws-cdk/core/lib/asset-staging.ts
@@ -4,7 +4,6 @@ import * as path from 'path';
 import * as cxapi from '@aws-cdk/cx-api';
 import { Construct } from 'constructs';
 import * as fs from 'fs-extra';
-import * as minimatch from 'minimatch';
 import { AssetHashType, AssetOptions, FileAssetPackaging } from './assets';
 import { BundlingOptions, BundlingOutput } from './bundling';
 import { FileSystem, FingerprintOptions } from './fs';
@@ -188,9 +187,7 @@ export class AssetStaging extends CoreConstruct {
     let skip = false;
     if (props.bundling) {
       // Check if we actually have to bundle for this stack
-      const bundlingStacks: string[] = this.node.tryGetContext(cxapi.BUNDLING_STACKS) ?? ['*'];
-      // bundlingStacks is of the form `Stage/Stack`, convert it to `Stage-Stack` before comparing to stack name
-      skip = !bundlingStacks.find(pattern => minimatch(Stack.of(this).stackName, pattern.replace('/', '-')));
+      skip = !Stack.of(this).bundlingRequired;
       const bundling = props.bundling;
       stageThisAsset = () => this.stageByBundling(bundling, skip);
     } else {
diff --git a/packages/@aws-cdk/core/lib/stack.ts b/packages/@aws-cdk/core/lib/stack.ts
index 0efd45fc14b3f..d6278d05834e3 100644
--- a/packages/@aws-cdk/core/lib/stack.ts
+++ b/packages/@aws-cdk/core/lib/stack.ts
@@ -3,6 +3,7 @@ import * as path from 'path';
 import * as cxschema from '@aws-cdk/cloud-assembly-schema';
 import * as cxapi from '@aws-cdk/cx-api';
 import { IConstruct, Construct, Node } from 'constructs';
+import * as minimatch from 'minimatch';
 import { Annotations } from './annotations';
 import { App } from './app';
 import { Arn, ArnComponents, ArnFormat } from './arn';
@@ -1153,6 +1154,19 @@ export class Stack extends CoreConstruct implements ITaggable {
 
     return makeStackName(ids);
   }
+
+  /**
+   * Indicates whether the stack requires bundling or not
+   */
+  public get bundlingRequired() {
+    const bundlingStacks: string[] = this.node.tryGetContext(cxapi.BUNDLING_STACKS) ?? ['*'];
+
+    // bundlingStacks is of the form `Stage/Stack`, convert it to `Stage-Stack` before comparing to stack name
+    return bundlingStacks.some(pattern => minimatch(
+      this.stackName,
+      pattern.replace('/', '-'),
+    ));
+  }
 }
 
 function merge(template: any, fragment: any): void {
diff --git a/packages/@aws-cdk/core/test/stack.test.ts b/packages/@aws-cdk/core/test/stack.test.ts
index b344dbbbff0be..e41796bccb624 100644
--- a/packages/@aws-cdk/core/test/stack.test.ts
+++ b/packages/@aws-cdk/core/test/stack.test.ts
@@ -1191,6 +1191,38 @@ describe('stack', () => {
     expect(new Stack(app, 'Stack', { analyticsReporting: true })._versionReportingEnabled).toBeDefined();
 
   });
+
+  test('requires bundling when wildcard is specified in BUNDLING_STACKS', () => {
+    const app = new App();
+    const stack = new Stack(app, 'Stack');
+    stack.node.setContext(cxapi.BUNDLING_STACKS, ['*']);
+    expect(stack.bundlingRequired).toBe(true);
+
+  });
+
+  test('requires bundling when stackName has an exact match in BUNDLING_STACKS', () => {
+    const app = new App();
+    const stack = new Stack(app, 'Stack');
+    stack.node.setContext(cxapi.BUNDLING_STACKS, ['Stack']);
+    expect(stack.bundlingRequired).toBe(true);
+
+  });
+
+  test('does not require bundling when no item from BUILDING_STACKS matches stackName', () => {
+    const app = new App();
+    const stack = new Stack(app, 'Stack');
+    stack.node.setContext(cxapi.BUNDLING_STACKS, ['Stac']);
+    expect(stack.bundlingRequired).toBe(false);
+
+  });
+
+  test('does not require bundling when BUNDLING_STACKS is empty', () => {
+    const app = new App();
+    const stack = new Stack(app, 'Stack');
+    stack.node.setContext(cxapi.BUNDLING_STACKS, []);
+    expect(stack.bundlingRequired).toBe(false);
+
+  });
 });
 
 describe('regionalFact', () => {