diff --git a/packages/aws-cdk-lib/core/test/stack-synthesis/new-style-synthesis.test.ts b/packages/aws-cdk-lib/core/test/stack-synthesis/new-style-synthesis.test.ts
index bd97490845cc2..097599934c060 100644
--- a/packages/aws-cdk-lib/core/test/stack-synthesis/new-style-synthesis.test.ts
+++ b/packages/aws-cdk-lib/core/test/stack-synthesis/new-style-synthesis.test.ts
@@ -105,7 +105,7 @@ describe('new style synthesis', () => {
 
   });
 
-  test('can set session tags on default stack synthesizer', () => {
+  test('can set role additional options tags on default stack synthesizer', () => {
     // GIVEN
     stack = new Stack(app, 'SessionTagsStack', {
       synthesizer: new DefaultStackSynthesizer({
@@ -122,6 +122,9 @@ describe('new style synthesis', () => {
           Tags: [{ Key: 'Department', Value: 'Engineering-LookupRoleTag' }],
         },
       }),
+      env: {
+        account: '111111111111', region: 'us-east-1',
+      },
     });
 
     stack.synthesizer.addFileAsset({
@@ -135,9 +138,15 @@ describe('new style synthesis', () => {
       sourceHash: 'dockerHash',
     });
 
+    ContextProvider.getValue(stack, {
+      provider: cxschema.ContextProvider.VPC_PROVIDER,
+      props: {},
+      dummyValue: undefined,
+    }).value;
+
     // THEN
     const asm = app.synth();
-    const manifest = app.synth().getStackByName('SessionTagsStack').manifest;
+    const manifest = asm.getStackByName('SessionTagsStack').manifest;
     // Validates that the deploy and lookup role session tags were set in the Manifest:
     expect((manifest.properties as cxschema.AwsCloudFormationStackProperties).assumeRoleAdditionalOptions?.Tags).toEqual([{ Key: 'Department', Value: 'Engineering-DeployRoleTag' }]);
     expect((manifest.properties as cxschema.AwsCloudFormationStackProperties).lookupRole?.assumeRoleAdditionalOptions?.Tags).toEqual([{ Key: 'Department', Value: 'Engineering-LookupRoleTag' }]);
@@ -148,6 +157,10 @@ describe('new style synthesis', () => {
     // Validates that the image and file asset session tags were set in the asset manifest:
     expect(assetManifestJSON.dockerImages?.dockerHash.destinations['current_account-current_region'].assumeRoleAdditionalOptions?.Tags).toEqual([{ Key: 'Department', Value: 'Engineering-ImageAssetTag' }]);
     expect(assetManifestJSON.files?.fileHash.destinations['current_account-current_region'].assumeRoleAdditionalOptions?.Tags).toEqual([{ Key: 'Department', Value: 'Engineering-FileAssetTag' }]);
+
+    // assert that lookup role options are added to the missing lookup context
+    expect(asm.manifest.missing![0].props.assumeRoleAdditionalOptions).toEqual({});
+
   });
 
   test('customize version parameter', () => {
@@ -233,6 +246,29 @@ describe('new style synthesis', () => {
 
   });
 
+  test('generates missing context with the lookup role external id as one of the missing context properties', () => {
+    // GIVEN
+    stack = new Stack(app, 'Stack2', {
+      synthesizer: new DefaultStackSynthesizer({
+        generateBootstrapVersionRule: false,
+        lookupRoleExternalId: 'External',
+      }),
+      env: {
+        account: '111111111111', region: 'us-east-1',
+      },
+    });
+    ContextProvider.getValue(stack, {
+      provider: cxschema.ContextProvider.VPC_PROVIDER,
+      props: {},
+      dummyValue: undefined,
+    }).value;
+
+    // THEN
+    const assembly = app.synth();
+    expect(assembly.manifest.missing![0].props.lookupRoleExternalId).toEqual('External');
+
+  });
+
   test('nested Stack uses the lookup role ARN of the parent stack', () => {
     // GIVEN
     const myapp = new App();