diff --git a/packages/@aws-cdk/aws-iam/README.md b/packages/@aws-cdk/aws-iam/README.md
index 8cf5978aaa7c6..b54a0bff34fc4 100644
--- a/packages/@aws-cdk/aws-iam/README.md
+++ b/packages/@aws-cdk/aws-iam/README.md
@@ -433,6 +433,18 @@ const user = User.fromUserAttributes(stack, 'MyImportedUserByAttributes', {
 });
 ```
 
+To add a user to a group (both for a new and imported user/group):
+
+```ts
+const user = new User(this, 'MyUser'); // or User.fromUserName(stack, 'User', 'johnsmith');
+const group = new Group(this, 'MyGroup'); // or Group.fromGroupArn(stack, 'Group', 'arn:aws:iam::account-id:group/group-name');
+
+user.addToGroup(group);
+// or
+group.addUser(user);
+```
+
+
 ## Features
 
  * Policy name uniqueness is enforced. If two policies by the same name are attached to the same
diff --git a/packages/@aws-cdk/aws-iam/lib/user.ts b/packages/@aws-cdk/aws-iam/lib/user.ts
index 5c8f6418a9bb8..4874e84f791df 100644
--- a/packages/@aws-cdk/aws-iam/lib/user.ts
+++ b/packages/@aws-cdk/aws-iam/lib/user.ts
@@ -1,7 +1,7 @@
 import { Arn, Aws, Lazy, Resource, SecretValue, Stack } from '@aws-cdk/core';
 import { Construct } from 'constructs';
 import { IGroup } from './group';
-import { CfnUser } from './iam.generated';
+import { CfnUser, CfnUserToGroupAddition } from './iam.generated';
 import { IIdentity } from './identity-base';
 import { IManagedPolicy } from './managed-policy';
 import { Policy } from './policy';
@@ -181,6 +181,7 @@ export class User extends Resource implements IIdentity, IUser {
       public readonly policyFragment: PrincipalPolicyFragment = new ArnPrincipal(attrs.userArn).policyFragment;
       private readonly attachedPolicies = new AttachedPolicies();
       private defaultPolicy?: Policy;
+      private groupId = 0;
 
       public addToPolicy(statement: PolicyStatement): boolean {
         return this.addToPrincipalPolicy(statement).statementAdded;
@@ -195,8 +196,12 @@ export class User extends Resource implements IIdentity, IUser {
         return { statementAdded: true, policyDependable: this.defaultPolicy };
       }
 
-      public addToGroup(_group: IGroup): void {
-        throw new Error('Cannot add imported User to Group');
+      public addToGroup(group: IGroup): void {
+        new CfnUserToGroupAddition(Stack.of(group), `${this.userName}Group${this.groupId}`, {
+          groupName: group.groupName,
+          users: [this.userName],
+        });
+        this.groupId += 1;
       }
 
       public attachInlinePolicy(policy: Policy): void {
@@ -229,7 +234,7 @@ export class User extends Resource implements IIdentity, IUser {
   public readonly userArn: string;
 
   /**
-   * Returns the permissions boundary attached to this user
+   * Returns the permissions boundary attached  to this user
    */
   public readonly permissionsBoundary?: IManagedPolicy;
 
diff --git a/packages/@aws-cdk/aws-iam/test/user.test.ts b/packages/@aws-cdk/aws-iam/test/user.test.ts
index af30005bec513..5cc42ae015619 100644
--- a/packages/@aws-cdk/aws-iam/test/user.test.ts
+++ b/packages/@aws-cdk/aws-iam/test/user.test.ts
@@ -1,6 +1,6 @@
 import '@aws-cdk/assert-internal/jest';
 import { App, SecretValue, Stack } from '@aws-cdk/core';
-import { ManagedPolicy, Policy, PolicyStatement, User } from '../lib';
+import { Group, ManagedPolicy, Policy, PolicyStatement, User } from '../lib';
 
 describe('IAM user', () => {
   test('default user', () => {
@@ -177,4 +177,35 @@ describe('IAM user', () => {
       },
     });
   });
+
+  test('addToGroup for imported user', () => {
+    // GIVEN
+    const stack = new Stack();
+    const user = User.fromUserName(stack, 'ImportedUser', 'john');
+    const group = new Group(stack, 'Group');
+    const otherGroup = new Group(stack, 'OtherGroup');
+
+    // WHEN
+    user.addToGroup(group);
+    otherGroup.addUser(user);
+
+    // THEN
+    expect(stack).toHaveResource('AWS::IAM::UserToGroupAddition', {
+      GroupName: {
+        Ref: 'GroupC77FDACD',
+      },
+      Users: [
+        'john',
+      ],
+    });
+
+    expect(stack).toHaveResource('AWS::IAM::UserToGroupAddition', {
+      GroupName: {
+        Ref: 'OtherGroup85E5C653',
+      },
+      Users: [
+        'john',
+      ],
+    });
+  });
 });