diff --git a/packages/@aws-cdk/toolkit-lib/lib/api/deployments/deployments.ts b/packages/@aws-cdk/toolkit-lib/lib/api/deployments/deployments.ts
index 2329e6e50..d27ed7130 100644
--- a/packages/@aws-cdk/toolkit-lib/lib/api/deployments/deployments.ts
+++ b/packages/@aws-cdk/toolkit-lib/lib/api/deployments/deployments.ts
@@ -321,7 +321,12 @@ export class Deployments {
 
   private readonly publisherCache = new Map<cdk_assets.AssetManifest, Map<string, cdk_assets.AssetPublishing>>();
 
-  private _allowCrossAccountAssetPublishing: boolean | undefined;
+  // Cache by resolved environment: this Deployments instance is reused across every
+  // stack in a single `cdk deploy` invocation, and stacks can target different
+  // accounts/regions. determineAllowCrossAccountAssetPublishing() reads that specific
+  // environment's bootstrap stack, so caching a single un-keyed value would silently
+  // reuse the first stack's environment's answer for every other stack's environment.
+  private readonly allowCrossAccountAssetPublishingCache = new Map<string, boolean>();
 
   private readonly ioHelper: IoHelper;
 
@@ -744,11 +749,18 @@ export class Deployments {
   }
 
   private async allowCrossAccountAssetPublishingForEnv(stack: cxapi.CloudFormationStackArtifact): Promise<boolean> {
-    if (this._allowCrossAccountAssetPublishing === undefined) {
-      const env = await this.envs.accessStackForReadOnlyStackOperations(stack);
-      this._allowCrossAccountAssetPublishing = await determineAllowCrossAccountAssetPublishing(env.sdk, this.ioHelper, this.props.toolkitStackName);
+    const resolvedEnvironment = await this.envs.resolveStackEnvironment(stack);
+    const envKey = `${resolvedEnvironment.account}:${resolvedEnvironment.region}`;
+
+    const cached = this.allowCrossAccountAssetPublishingCache.get(envKey);
+    if (cached !== undefined) {
+      return cached;
     }
-    return this._allowCrossAccountAssetPublishing;
+
+    const env = await this.envs.accessStackForReadOnlyStackOperations(stack);
+    const allowed = await determineAllowCrossAccountAssetPublishing(env.sdk, this.ioHelper, this.props.toolkitStackName);
+    this.allowCrossAccountAssetPublishingCache.set(envKey, allowed);
+    return allowed;
   }
 
   /**
diff --git a/packages/@aws-cdk/toolkit-lib/test/api/deployments/cloudformation-deployments.test.ts b/packages/@aws-cdk/toolkit-lib/test/api/deployments/cloudformation-deployments.test.ts
index 7e06b25b5..d92a66437 100644
--- a/packages/@aws-cdk/toolkit-lib/test/api/deployments/cloudformation-deployments.test.ts
+++ b/packages/@aws-cdk/toolkit-lib/test/api/deployments/cloudformation-deployments.test.ts
@@ -12,6 +12,7 @@ import { GetParameterCommand } from '@aws-sdk/client-ssm';
 import { CloudFormationStack } from '../../../lib/api/cloudformation';
 import { Deployments } from '../../../lib/api/deployments';
 import * as cfnApi from '../../../lib/api/deployments/cfn-api';
+import { determineAllowCrossAccountAssetPublishing } from '../../../lib/api/deployments/checks';
 import { deployStack, destroyStack } from '../../../lib/api/deployments/deploy-stack';
 import { ToolkitInfo } from '../../../lib/api/toolkit-info';
 import { testStack } from '../../_helpers/assembly';
@@ -29,6 +30,7 @@ import { FakeCloudformationStack } from '../_helpers/fake-cloudformation-stack';
 
 jest.mock('../../../lib/api/deployments/deploy-stack');
 jest.mock('../../../lib/api/deployments/asset-publishing');
+jest.mock('../../../lib/api/deployments/checks');
 
 let sdkProvider: MockSdkProvider;
 let sdk: MockSdk;
@@ -1344,6 +1346,44 @@ describe('cachedPublisher', () => {
   });
 });
 
+describe('allowCrossAccountAssetPublishingForEnv', () => {
+  // Regression test: the cross-account-asset-publishing answer used to be cached in a
+  // single un-keyed instance field, so the first stack's environment's answer was
+  // silently reused for every other stack's environment on the same Deployments
+  // instance (which is reused for every stack in one `cdk deploy` invocation).
+  test('does not reuse the answer across different environments', async () => {
+    sdkProvider.forEnvironment = jest.fn().mockImplementation(() => ({ sdk: new MockSdk() }));
+    const mockDetermine = determineAllowCrossAccountAssetPublishing as jest.Mock;
+    mockDetermine.mockResolvedValueOnce(false).mockResolvedValueOnce(true);
+
+    const stackA = testStack({ stackName: 'StackA', env: 'aws://111111111111/us-east-1' });
+    const stackB = testStack({ stackName: 'StackB', env: 'aws://222222222222/eu-west-1' });
+
+    const allowedForA = await (deployments as any).allowCrossAccountAssetPublishingForEnv(stackA);
+    const allowedForB = await (deployments as any).allowCrossAccountAssetPublishingForEnv(stackB);
+
+    expect(allowedForA).toBe(false);
+    expect(allowedForB).toBe(true);
+    expect(mockDetermine).toHaveBeenCalledTimes(2);
+  });
+
+  test('reuses the cached answer for repeat calls with the same environment', async () => {
+    sdkProvider.forEnvironment = jest.fn().mockImplementation(() => ({ sdk: new MockSdk() }));
+    const mockDetermine = determineAllowCrossAccountAssetPublishing as jest.Mock;
+    mockDetermine.mockResolvedValueOnce(true);
+
+    const stackA = testStack({ stackName: 'StackA', env: 'aws://111111111111/us-east-1' });
+    const stackAAgain = testStack({ stackName: 'StackA', env: 'aws://111111111111/us-east-1' });
+
+    const first = await (deployments as any).allowCrossAccountAssetPublishingForEnv(stackA);
+    const second = await (deployments as any).allowCrossAccountAssetPublishingForEnv(stackAAgain);
+
+    expect(first).toBe(true);
+    expect(second).toBe(true);
+    expect(mockDetermine).toHaveBeenCalledTimes(1);
+  });
+});
+
 function pushStackResourceSummaries(stackName: string, ...items: StackResourceSummary[]) {
   if (!currentCfnStackResources[stackName]) {
     currentCfnStackResources[stackName] = [];