diff --git a/packages/aws-cdk/lib/api/cloudformation-deployments.ts b/packages/aws-cdk/lib/api/cloudformation-deployments.ts
index 72c48bb109ee7..a4438ff0ca8f7 100644
--- a/packages/aws-cdk/lib/api/cloudformation-deployments.ts
+++ b/packages/aws-cdk/lib/api/cloudformation-deployments.ts
@@ -96,14 +96,20 @@ export async function prepareSdkWithLookupRoleFor(
       if (version < stack.lookupRole.requiresBootstrapStackVersion) {
         throw new Error(`Bootstrap stack version '${stack.lookupRole.requiresBootstrapStackVersion}' is required, found version '${version}'.`);
       }
-    } else if (!stackSdk.didAssumeRole) {
+      // we may not have assumed the lookup role because one was not provided
+      // if that is the case then don't print the upgrade warning
+    } else if (!stackSdk.didAssumeRole && stack.lookupRole?.requiresBootstrapStackVersion) {
       warning(upgradeMessage);
     }
     return { ...stackSdk, resolvedEnvironment };
   } catch (e) {
     debug(e);
-    warning(warningMessage);
-    warning(upgradeMessage);
+    // only print out the warnings if the lookupRole exists AND there is a required
+    // bootstrap version, otherwise the warnings will print `undefined`
+    if (stack.lookupRole && stack.lookupRole.requiresBootstrapStackVersion) {
+      warning(warningMessage);
+      warning(upgradeMessage);
+    }
     throw (e);
   }
 }
diff --git a/packages/aws-cdk/test/cdk-toolkit.test.ts b/packages/aws-cdk/test/cdk-toolkit.test.ts
index 7b8f96d5d948c..c7ee3b87130fc 100644
--- a/packages/aws-cdk/test/cdk-toolkit.test.ts
+++ b/packages/aws-cdk/test/cdk-toolkit.test.ts
@@ -127,6 +127,13 @@ describe('readCurrentTemplate', () => {
             },
           },
         },
+        {
+          stackName: 'Test-Stack-A',
+          template,
+          properties: {
+            assumeRoleArn: 'bloop:${AWS::Region}:${AWS::AccountId}',
+          },
+        },
       ],
     });
     mockForEnvironment = jest.fn().mockImplementation(() => { return { sdk: mockCloudExecutable.sdkProvider.sdk, didAssumeRole: true }; });
@@ -145,6 +152,11 @@ describe('readCurrentTemplate', () => {
               StackStatus: 'CREATE_COMPLETE',
               CreationTime: new Date(),
             },
+            {
+              StackName: 'Test-Stack-A',
+              StackStatus: 'CREATE_COMPLETE',
+              CreationTime: new Date(),
+            },
           ],
         };
       },
@@ -329,6 +341,38 @@ describe('readCurrentTemplate', () => {
       assumeRoleArn: 'bloop:here:123456789012',
     });
   });
+
+  test('do not print warnings if lookup role not provided in stack artifact', async () => {
+    // GIVEN
+    mockCloudExecutable.sdkProvider.stubSSM({
+      getParameter() {
+        return {};
+      },
+    });
+    const cdkToolkit = new CdkToolkit({
+      cloudExecutable: mockCloudExecutable,
+      configuration: mockCloudExecutable.configuration,
+      sdkProvider: mockCloudExecutable.sdkProvider,
+      cloudFormation: new CloudFormationDeployments({ sdkProvider: mockCloudExecutable.sdkProvider }),
+    });
+
+    // WHEN
+    await cdkToolkit.deploy({
+      selector: { patterns: ['Test-Stack-A'] },
+    });
+
+    // THEN
+    expect(flatten(stderrMock.mock.calls)).not.toEqual(expect.arrayContaining([
+      expect.stringMatching(/Could not assume/),
+      expect.stringMatching(/please upgrade to bootstrap version/),
+    ]));
+    expect(mockCloudExecutable.sdkProvider.sdk.ssm).not.toHaveBeenCalled();
+    expect(mockForEnvironment.mock.calls.length).toEqual(2);
+    expect(mockForEnvironment.mock.calls[0][2]).toEqual({
+      assumeRoleArn: undefined,
+      assumeRoleExternalId: undefined,
+    });
+  });
 });
 
 describe('deploy', () => {