diff --git a/packages/@aws-cdk-testing/cli-integ/resources/cdk-apps/app/app.js b/packages/@aws-cdk-testing/cli-integ/resources/cdk-apps/app/app.js
index 673806b72ec56..dd2797823198f 100755
--- a/packages/@aws-cdk-testing/cli-integ/resources/cdk-apps/app/app.js
+++ b/packages/@aws-cdk-testing/cli-integ/resources/cdk-apps/app/app.js
@@ -431,6 +431,20 @@ class LambdaStack extends cdk.Stack {
   }
 }
 
+class IamRolesStack extends cdk.Stack {
+  constructor(parent, id, props) {
+    super(parent, id, props);
+
+    // Environment variabile is used to create a bunch of roles to test
+    // that large diff templates are uploaded to S3 to create the changeset.
+    for(let i = 1; i <= Number(process.env.NUMBER_OF_ROLES) ; i++) {
+      new iam.Role(this, `Role${i}`, {
+        assumedBy: new iam.ServicePrincipal('lambda.amazonaws.com'),
+      });
+    }
+  }
+}
+
 class SessionTagsStack extends cdk.Stack {
   constructor(parent, id, props) {
     super(parent, id, {
@@ -778,6 +792,8 @@ switch (stackSet) {
 
     new LambdaStack(app, `${stackPrefix}-lambda`);
 
+    new IamRolesStack(app, `${stackPrefix}-iam-roles`);
+
     if (process.env.ENABLE_VPC_TESTING == 'IMPORT') {
       // this stack performs a VPC lookup so we gate synth
       const env = { account: process.env.CDK_DEFAULT_ACCOUNT, region: process.env.CDK_DEFAULT_REGION };
diff --git a/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/cli.integtest.ts b/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/cli.integtest.ts
index 682fcf54f5227..8efebdec07875 100644
--- a/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/cli.integtest.ts
+++ b/packages/@aws-cdk-testing/cli-integ/tests/cli-integ-tests/cli.integtest.ts
@@ -1032,6 +1032,30 @@ integTest(
   }),
 );
 
+integTest(
+  'cdk diff with large changeset does not fail',
+  withDefaultFixture(async (fixture) => {
+    // GIVEN - small initial stack with only ane IAM role
+    await fixture.cdkDeploy('iam-roles', {
+      modEnv: {
+        NUMBER_OF_ROLES: '1',
+      },
+    });
+
+    // WHEN - adding 200 roles to the same stack to create a large diff
+    const diff = await fixture.cdk(['diff', fixture.fullStackName('iam-roles')], {
+      verbose: true,
+      modEnv: {
+        NUMBER_OF_ROLES: '200',
+      },
+    });
+
+    // Assert that the CLI assumes the file publishing role:
+    expect(diff).toMatch(/Assuming role .*file-publishing-role/);
+    expect(diff).toContain('success: Published');
+  }),
+);
+
 integTest(
   'cdk diff --security-only successfully outputs sso-permission-set-without-managed-policy information',
   withDefaultFixture(async (fixture) => {
diff --git a/packages/aws-cdk/lib/api/deployments.ts b/packages/aws-cdk/lib/api/deployments.ts
index f3aae0bec571a..d5b6f8a63e987 100644
--- a/packages/aws-cdk/lib/api/deployments.ts
+++ b/packages/aws-cdk/lib/api/deployments.ts
@@ -17,7 +17,8 @@ import { StackActivityMonitor, StackActivityProgress } from './util/cloudformati
 import { StackEventPoller } from './util/cloudformation/stack-event-poller';
 import { RollbackChoice } from './util/cloudformation/stack-status';
 import { replaceEnvPlaceholders } from './util/placeholders';
-import { makeBodyParameterAndUpload } from './util/template-body-parameter';
+import { makeBodyParameter } from './util/template-body-parameter';
+import { AssetManifestBuilder } from '../util/asset-manifest-builder';
 import { buildAssets, publishAssets, BuildAssetsOptions, PublishAssetsOptions, PublishingAws, EVENT_TO_LOGGER } from '../util/asset-publishing';
 
 const BOOTSTRAP_STACK_VERSION_FOR_ROLLBACK = 23;
@@ -426,11 +427,11 @@ export class Deployments {
     const cfn = stackSdk.cloudFormation();
 
     // Upload the template, if necessary, before passing it to CFN
-    const cfnParam = await makeBodyParameterAndUpload(
+    const cfnParam = await makeBodyParameter(
       stackArtifact,
       resolvedEnvironment,
+      new AssetManifestBuilder(),
       envResources,
-      this.sdkProvider,
       stackSdk);
 
     const response = await cfn.getTemplateSummary(cfnParam).promise();
diff --git a/packages/aws-cdk/lib/api/util/cloudformation.ts b/packages/aws-cdk/lib/api/util/cloudformation.ts
index 2361871e2bef0..27822ca4c8378 100644
--- a/packages/aws-cdk/lib/api/util/cloudformation.ts
+++ b/packages/aws-cdk/lib/api/util/cloudformation.ts
@@ -3,10 +3,12 @@ import { DescribeChangeSetOutput } from '@aws-cdk/cloudformation-diff';
 import { SSMPARAM_NO_INVALIDATE } from '@aws-cdk/cx-api';
 import * as cxapi from '@aws-cdk/cx-api';
 import { CloudFormation } from 'aws-sdk';
+import { AssetManifest, FileManifestEntry } from 'cdk-assets';
 import { StackStatus } from './cloudformation/stack-status';
-import { makeBodyParameterAndUpload, TemplateBodyParameter } from './template-body-parameter';
+import { makeBodyParameter, TemplateBodyParameter } from './template-body-parameter';
 import { debug } from '../../logging';
 import { deserializeStructure } from '../../serialize';
+import { AssetManifestBuilder } from '../../util/asset-manifest-builder';
 import { SdkProvider } from '../aws-auth';
 import { Deployments } from '../deployments';
 
@@ -338,14 +340,54 @@ export async function createDiffChangeSet(options: PrepareChangeSetOptions): Pro
   return uploadBodyParameterAndCreateChangeSet(options);
 }
 
+/**
+ * Returns all file entries from an AssetManifestArtifact. This is used in the
+ * `uploadBodyParameterAndCreateChangeSet` function to find all template asset files to build and publish.
+ *
+ * Returns a tuple of [AssetManifest, FileManifestEntry[]]
+ */
+function fileEntriesFromAssetManifestArtifact(artifact: cxapi.AssetManifestArtifact): [AssetManifest, FileManifestEntry[]] {
+  const assets: (FileManifestEntry)[] = [];
+  const fileName = artifact.file;
+  const assetManifest = AssetManifest.fromFile(fileName);
+
+  assetManifest.entries.forEach(entry => {
+    if (entry.type === 'file') {
+      const source = (entry as FileManifestEntry).source;
+      if (source.path && (source.path.endsWith('.template.json'))) {
+        assets.push(entry as FileManifestEntry);
+      }
+    }
+  });
+  return [assetManifest, assets];
+}
+
 async function uploadBodyParameterAndCreateChangeSet(options: PrepareChangeSetOptions): Promise<DescribeChangeSetOutput | undefined> {
   try {
+    for (const artifact of options.stack.dependencies) {
+      // Skip artifact if it is not an Asset Manifest Artifact
+      if (!cxapi.AssetManifestArtifact.isAssetManifestArtifact(artifact)) {
+        continue;
+      }
+
+      // Build and publish each file entry of the Asset Manifest Artifact:
+      const [assetManifest, file_entries] = fileEntriesFromAssetManifestArtifact(artifact);
+      for (const entry of file_entries) {
+        await options.deployments.buildSingleAsset(artifact, assetManifest, entry, {
+          stack: options.stack,
+        });
+        await options.deployments.publishSingleAsset(assetManifest, entry, {
+          stack: options.stack,
+        });
+      }
+    }
     const preparedSdk = (await options.deployments.prepareSdkWithDeployRole(options.stack));
-    const bodyParameter = await makeBodyParameterAndUpload(
+
+    const bodyParameter = await makeBodyParameter(
       options.stack,
       preparedSdk.resolvedEnvironment,
+      new AssetManifestBuilder(),
       preparedSdk.envResources,
-      options.sdkProvider,
       preparedSdk.stackSdk,
     );
     const cfn = preparedSdk.stackSdk.cloudFormation();
diff --git a/packages/aws-cdk/lib/api/util/template-body-parameter.ts b/packages/aws-cdk/lib/api/util/template-body-parameter.ts
index 0b036cc2cd244..87a70edd973ad 100644
--- a/packages/aws-cdk/lib/api/util/template-body-parameter.ts
+++ b/packages/aws-cdk/lib/api/util/template-body-parameter.ts
@@ -5,9 +5,8 @@ import * as fs from 'fs-extra';
 import { debug, error } from '../../logging';
 import { toYAML } from '../../serialize';
 import { AssetManifestBuilder } from '../../util/asset-manifest-builder';
-import { publishAssets } from '../../util/asset-publishing';
 import { contentHash } from '../../util/content-hash';
-import { ISDK, SdkProvider } from '../aws-auth';
+import { ISDK } from '../aws-auth';
 import { EnvironmentResources } from '../environment-resources';
 
 export type TemplateBodyParameter = {
@@ -85,34 +84,6 @@ export async function makeBodyParameter(
   return { TemplateURL: templateURL };
 }
 
-/**
- * Prepare a body parameter for CFN, performing the upload
- *
- * Return it as-is if it is small enough to pass in the API call,
- * upload to S3 and return the coordinates if it is not.
- */
-export async function makeBodyParameterAndUpload(
-  stack: cxapi.CloudFormationStackArtifact,
-  resolvedEnvironment: cxapi.Environment,
-  resources: EnvironmentResources,
-  sdkProvider: SdkProvider,
-  sdk: ISDK,
-  overrideTemplate?: any): Promise<TemplateBodyParameter> {
-
-  // We don't have access to the actual asset manifest here, so pretend that the
-  // stack doesn't have a pre-published URL.
-  const forceUploadStack = Object.create(stack, {
-    stackTemplateAssetObjectUrl: { value: undefined },
-  });
-
-  const builder = new AssetManifestBuilder();
-  const bodyparam = await makeBodyParameter(forceUploadStack, resolvedEnvironment, builder, resources, sdk, overrideTemplate);
-  const manifest = builder.toManifest(stack.assembly.directory);
-  await publishAssets(manifest, sdkProvider, resolvedEnvironment, { quiet: true });
-
-  return bodyparam;
-}
-
 /**
  * Format an S3 URL in the manifest for use with CloudFormation
  *