diff --git a/packages/@aws-cdk/aws-ec2/README.md b/packages/@aws-cdk/aws-ec2/README.md
index 4f77528d922e6..9b24604d546ab 100644
--- a/packages/@aws-cdk/aws-ec2/README.md
+++ b/packages/@aws-cdk/aws-ec2/README.md
@@ -1404,6 +1404,21 @@ instance.userData.addExecuteFileCommand({
 asset.grantRead(instance.role);
 ```
 
+### Persisting user data
+
+By default, EC2 UserData is run once on only the first time that an instance is started. It is possible to make the
+user data script run on every start of the instance. 
+
+When creating a Windows UserData you can use the `persist` option to set whether or not to add 
+`<persist>true</persist>` [to the user data script](https://docs.aws.amazon.com/AWSEC2/latest/WindowsGuide/ec2-windows-user-data.html#user-data-scripts). it can be used as follows:
+
+```ts
+const windowsUserData = UserData.forWindows({ persist: true });
+```
+
+For a Linux instance, this can be accomplished by using a Multipart user data to configure cloud-config as detailed
+in: https://aws.amazon.com/premiumsupport/knowledge-center/execute-user-data-ec2/
+
 ### Multipart user data
 
 In addition, to above the `MultipartUserData` can be used to change instance startup behavior. Multipart user data are composed
diff --git a/packages/@aws-cdk/aws-ec2/lib/user-data.ts b/packages/@aws-cdk/aws-ec2/lib/user-data.ts
index 82e256b9a895a..2b59c63138bef 100644
--- a/packages/@aws-cdk/aws-ec2/lib/user-data.ts
+++ b/packages/@aws-cdk/aws-ec2/lib/user-data.ts
@@ -14,6 +14,24 @@ export interface LinuxUserDataOptions {
   readonly shebang?: string;
 }
 
+/**
+ * Options when constructing UserData for Windows
+ */
+export interface WindowsUserDataOptions {
+  /**
+   * Set to true to set this userdata to persist through an instance reboot; allowing
+   * it to run on every instance start.
+   * By default, UserData is run only once during the first instance launch.
+   *
+   * For more information, see:
+   * https://aws.amazon.com/premiumsupport/knowledge-center/execute-user-data-ec2/
+   * https://docs.aws.amazon.com/AWSEC2/latest/WindowsGuide/ec2-windows-user-data.html#user-data-scripts
+   *
+   * @default false
+   */
+  readonly persist?: boolean;
+}
+
 /**
  * Options when downloading files from S3
  */
@@ -78,8 +96,8 @@ export abstract class UserData {
   /**
    * Create a userdata object for Windows hosts
    */
-  public static forWindows(): UserData {
-    return new WindowsUserData();
+  public static forWindows(options: WindowsUserDataOptions = {}): UserData {
+    return new WindowsUserData(options);
   }
 
   /**
@@ -197,7 +215,7 @@ class WindowsUserData extends UserData {
   private readonly lines: string[] = [];
   private readonly onExitLines: string[] = [];
 
-  constructor() {
+  constructor(private readonly props: WindowsUserDataOptions = {}) {
     super();
   }
 
@@ -214,7 +232,7 @@ class WindowsUserData extends UserData {
       [...(this.renderOnExitLines()),
         ...this.lines,
         ...( this.onExitLines.length > 0 ? ['throw "Success"'] : [] )].join('\n')
-    }</powershell>`;
+    }</powershell>${(this.props.persist ?? false) ? '<persist>true</persist>' : ''}`;
   }
 
   public addS3DownloadCommand(params: S3DownloadOptions): string {
diff --git a/packages/@aws-cdk/aws-ec2/test/integ.userdata.ts b/packages/@aws-cdk/aws-ec2/test/integ.userdata.ts
new file mode 100644
index 0000000000000..002de7bd6cc29
--- /dev/null
+++ b/packages/@aws-cdk/aws-ec2/test/integ.userdata.ts
@@ -0,0 +1,18 @@
+#!/usr/bin/env node
+import * as cdk from '@aws-cdk/core';
+import * as ec2 from '../lib';
+
+const app = new cdk.App();
+const stack = new cdk.Stack(app, 'integ-userdata');
+
+const vpc = new ec2.Vpc(stack, 'IntegUserdataVpc');
+
+new ec2.Instance(stack, 'WindowsInstance', {
+  vpc,
+  vpcSubnets: { subnetType: ec2.SubnetType.PUBLIC },
+  instanceType: ec2.InstanceType.of(ec2.InstanceClass.BURSTABLE2, ec2.InstanceSize.MICRO),
+  machineImage: new ec2.WindowsImage(ec2.WindowsVersion.WINDOWS_SERVER_2022_ENGLISH_FULL_BASE),
+  userData: ec2.UserData.forWindows({ persist: true }),
+});
+
+app.synth();
diff --git a/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/cdk.out b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/cdk.out
new file mode 100644
index 0000000000000..8ecc185e9dbee
--- /dev/null
+++ b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/cdk.out
@@ -0,0 +1 @@
+{"version":"21.0.0"}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/integ-userdata.assets.json b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/integ-userdata.assets.json
new file mode 100644
index 0000000000000..a97d75d14b3b8
--- /dev/null
+++ b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/integ-userdata.assets.json
@@ -0,0 +1,19 @@
+{
+  "version": "21.0.0",
+  "files": {
+    "9f2c5f7def4ad32c13627dff08f2be0273546384a8fe510e265cc6a7083274e1": {
+      "source": {
+        "path": "integ-userdata.template.json",
+        "packaging": "file"
+      },
+      "destinations": {
+        "current_account-current_region": {
+          "bucketName": "cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}",
+          "objectKey": "9f2c5f7def4ad32c13627dff08f2be0273546384a8fe510e265cc6a7083274e1.json",
+          "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-file-publishing-role-${AWS::AccountId}-${AWS::Region}"
+        }
+      }
+    }
+  },
+  "dockerImages": {}
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/integ-userdata.template.json b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/integ-userdata.template.json
new file mode 100644
index 0000000000000..8fa5af6d1dd2b
--- /dev/null
+++ b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/integ-userdata.template.json
@@ -0,0 +1,541 @@
+{
+ "Resources": {
+  "IntegUserdataVpcDE2938ED": {
+   "Type": "AWS::EC2::VPC",
+   "Properties": {
+    "CidrBlock": "10.0.0.0/16",
+    "EnableDnsHostnames": true,
+    "EnableDnsSupport": true,
+    "InstanceTenancy": "default",
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85": {
+   "Type": "AWS::EC2::Subnet",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "AvailabilityZone": {
+     "Fn::Select": [
+      0,
+      {
+       "Fn::GetAZs": ""
+      }
+     ]
+    },
+    "CidrBlock": "10.0.0.0/18",
+    "MapPublicIpOnLaunch": true,
+    "Tags": [
+     {
+      "Key": "aws-cdk:subnet-name",
+      "Value": "Public"
+     },
+     {
+      "Key": "aws-cdk:subnet-type",
+      "Value": "Public"
+     },
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet1RouteTable7B342D96": {
+   "Type": "AWS::EC2::RouteTable",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet1RouteTableAssociation724A6375": {
+   "Type": "AWS::EC2::SubnetRouteTableAssociation",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPublicSubnet1RouteTable7B342D96"
+    },
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+    }
+   }
+  },
+  "IntegUserdataVpcPublicSubnet1DefaultRoute8F93CC39": {
+   "Type": "AWS::EC2::Route",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPublicSubnet1RouteTable7B342D96"
+    },
+    "DestinationCidrBlock": "0.0.0.0/0",
+    "GatewayId": {
+     "Ref": "IntegUserdataVpcIGWB657C40E"
+    }
+   },
+   "DependsOn": [
+    "IntegUserdataVpcVPCGWFA86AC6A"
+   ]
+  },
+  "IntegUserdataVpcPublicSubnet1EIP41DE8CA6": {
+   "Type": "AWS::EC2::EIP",
+   "Properties": {
+    "Domain": "vpc",
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet1NATGatewayC9F60940": {
+   "Type": "AWS::EC2::NatGateway",
+   "Properties": {
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+    },
+    "AllocationId": {
+     "Fn::GetAtt": [
+      "IntegUserdataVpcPublicSubnet1EIP41DE8CA6",
+      "AllocationId"
+     ]
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+     }
+    ]
+   },
+   "DependsOn": [
+    "IntegUserdataVpcPublicSubnet1DefaultRoute8F93CC39",
+    "IntegUserdataVpcPublicSubnet1RouteTableAssociation724A6375"
+   ]
+  },
+  "IntegUserdataVpcPublicSubnet2Subnet7EC040B5": {
+   "Type": "AWS::EC2::Subnet",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "AvailabilityZone": {
+     "Fn::Select": [
+      1,
+      {
+       "Fn::GetAZs": ""
+      }
+     ]
+    },
+    "CidrBlock": "10.0.64.0/18",
+    "MapPublicIpOnLaunch": true,
+    "Tags": [
+     {
+      "Key": "aws-cdk:subnet-name",
+      "Value": "Public"
+     },
+     {
+      "Key": "aws-cdk:subnet-type",
+      "Value": "Public"
+     },
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet2RouteTable98BA8E97": {
+   "Type": "AWS::EC2::RouteTable",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet2RouteTableAssociationBA5DC07F": {
+   "Type": "AWS::EC2::SubnetRouteTableAssociation",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPublicSubnet2RouteTable98BA8E97"
+    },
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPublicSubnet2Subnet7EC040B5"
+    }
+   }
+  },
+  "IntegUserdataVpcPublicSubnet2DefaultRoute90FCB645": {
+   "Type": "AWS::EC2::Route",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPublicSubnet2RouteTable98BA8E97"
+    },
+    "DestinationCidrBlock": "0.0.0.0/0",
+    "GatewayId": {
+     "Ref": "IntegUserdataVpcIGWB657C40E"
+    }
+   },
+   "DependsOn": [
+    "IntegUserdataVpcVPCGWFA86AC6A"
+   ]
+  },
+  "IntegUserdataVpcPublicSubnet2EIP662D51E3": {
+   "Type": "AWS::EC2::EIP",
+   "Properties": {
+    "Domain": "vpc",
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPublicSubnet2NATGatewayB25F84D3": {
+   "Type": "AWS::EC2::NatGateway",
+   "Properties": {
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPublicSubnet2Subnet7EC040B5"
+    },
+    "AllocationId": {
+     "Fn::GetAtt": [
+      "IntegUserdataVpcPublicSubnet2EIP662D51E3",
+      "AllocationId"
+     ]
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+     }
+    ]
+   },
+   "DependsOn": [
+    "IntegUserdataVpcPublicSubnet2DefaultRoute90FCB645",
+    "IntegUserdataVpcPublicSubnet2RouteTableAssociationBA5DC07F"
+   ]
+  },
+  "IntegUserdataVpcPrivateSubnet1Subnet4EFBF430": {
+   "Type": "AWS::EC2::Subnet",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "AvailabilityZone": {
+     "Fn::Select": [
+      0,
+      {
+       "Fn::GetAZs": ""
+      }
+     ]
+    },
+    "CidrBlock": "10.0.128.0/18",
+    "MapPublicIpOnLaunch": false,
+    "Tags": [
+     {
+      "Key": "aws-cdk:subnet-name",
+      "Value": "Private"
+     },
+     {
+      "Key": "aws-cdk:subnet-type",
+      "Value": "Private"
+     },
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PrivateSubnet1"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet1RouteTable63E39754": {
+   "Type": "AWS::EC2::RouteTable",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PrivateSubnet1"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet1RouteTableAssociation176A5EB9": {
+   "Type": "AWS::EC2::SubnetRouteTableAssociation",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPrivateSubnet1RouteTable63E39754"
+    },
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPrivateSubnet1Subnet4EFBF430"
+    }
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet1DefaultRoute03370EF2": {
+   "Type": "AWS::EC2::Route",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPrivateSubnet1RouteTable63E39754"
+    },
+    "DestinationCidrBlock": "0.0.0.0/0",
+    "NatGatewayId": {
+     "Ref": "IntegUserdataVpcPublicSubnet1NATGatewayC9F60940"
+    }
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet2SubnetAFD1E5B4": {
+   "Type": "AWS::EC2::Subnet",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "AvailabilityZone": {
+     "Fn::Select": [
+      1,
+      {
+       "Fn::GetAZs": ""
+      }
+     ]
+    },
+    "CidrBlock": "10.0.192.0/18",
+    "MapPublicIpOnLaunch": false,
+    "Tags": [
+     {
+      "Key": "aws-cdk:subnet-name",
+      "Value": "Private"
+     },
+     {
+      "Key": "aws-cdk:subnet-type",
+      "Value": "Private"
+     },
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PrivateSubnet2"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet2RouteTable7944CD08": {
+   "Type": "AWS::EC2::RouteTable",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc/PrivateSubnet2"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet2RouteTableAssociation3B0C1389": {
+   "Type": "AWS::EC2::SubnetRouteTableAssociation",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPrivateSubnet2RouteTable7944CD08"
+    },
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPrivateSubnet2SubnetAFD1E5B4"
+    }
+   }
+  },
+  "IntegUserdataVpcPrivateSubnet2DefaultRouteA120F4F4": {
+   "Type": "AWS::EC2::Route",
+   "Properties": {
+    "RouteTableId": {
+     "Ref": "IntegUserdataVpcPrivateSubnet2RouteTable7944CD08"
+    },
+    "DestinationCidrBlock": "0.0.0.0/0",
+    "NatGatewayId": {
+     "Ref": "IntegUserdataVpcPublicSubnet2NATGatewayB25F84D3"
+    }
+   }
+  },
+  "IntegUserdataVpcIGWB657C40E": {
+   "Type": "AWS::EC2::InternetGateway",
+   "Properties": {
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/IntegUserdataVpc"
+     }
+    ]
+   }
+  },
+  "IntegUserdataVpcVPCGWFA86AC6A": {
+   "Type": "AWS::EC2::VPCGatewayAttachment",
+   "Properties": {
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    },
+    "InternetGatewayId": {
+     "Ref": "IntegUserdataVpcIGWB657C40E"
+    }
+   }
+  },
+  "WindowsInstanceInstanceSecurityGroup3B6692A8": {
+   "Type": "AWS::EC2::SecurityGroup",
+   "Properties": {
+    "GroupDescription": "integ-userdata/WindowsInstance/InstanceSecurityGroup",
+    "SecurityGroupEgress": [
+     {
+      "CidrIp": "0.0.0.0/0",
+      "Description": "Allow all outbound traffic by default",
+      "IpProtocol": "-1"
+     }
+    ],
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/WindowsInstance"
+     }
+    ],
+    "VpcId": {
+     "Ref": "IntegUserdataVpcDE2938ED"
+    }
+   }
+  },
+  "WindowsInstanceInstanceRoleB7D73766": {
+   "Type": "AWS::IAM::Role",
+   "Properties": {
+    "AssumeRolePolicyDocument": {
+     "Statement": [
+      {
+       "Action": "sts:AssumeRole",
+       "Effect": "Allow",
+       "Principal": {
+        "Service": {
+         "Fn::Join": [
+          "",
+          [
+           "ec2.",
+           {
+            "Ref": "AWS::URLSuffix"
+           }
+          ]
+         ]
+        }
+       }
+      }
+     ],
+     "Version": "2012-10-17"
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/WindowsInstance"
+     }
+    ]
+   }
+  },
+  "WindowsInstanceInstanceProfile20441977": {
+   "Type": "AWS::IAM::InstanceProfile",
+   "Properties": {
+    "Roles": [
+     {
+      "Ref": "WindowsInstanceInstanceRoleB7D73766"
+     }
+    ]
+   }
+  },
+  "WindowsInstance4ABA347A": {
+   "Type": "AWS::EC2::Instance",
+   "Properties": {
+    "AvailabilityZone": {
+     "Fn::Select": [
+      0,
+      {
+       "Fn::GetAZs": ""
+      }
+     ]
+    },
+    "IamInstanceProfile": {
+     "Ref": "WindowsInstanceInstanceProfile20441977"
+    },
+    "ImageId": {
+     "Ref": "SsmParameterValueawsserviceamiwindowslatestWindowsServer2022EnglishFullBaseC96584B6F00A464EAD1953AFF4B05118Parameter"
+    },
+    "InstanceType": "t2.micro",
+    "SecurityGroupIds": [
+     {
+      "Fn::GetAtt": [
+       "WindowsInstanceInstanceSecurityGroup3B6692A8",
+       "GroupId"
+      ]
+     }
+    ],
+    "SubnetId": {
+     "Ref": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+    },
+    "Tags": [
+     {
+      "Key": "Name",
+      "Value": "integ-userdata/WindowsInstance"
+     }
+    ],
+    "UserData": {
+     "Fn::Base64": "<powershell></powershell><persist>true</persist>"
+    }
+   },
+   "DependsOn": [
+    "WindowsInstanceInstanceRoleB7D73766"
+   ]
+  }
+ },
+ "Parameters": {
+  "SsmParameterValueawsserviceamiwindowslatestWindowsServer2022EnglishFullBaseC96584B6F00A464EAD1953AFF4B05118Parameter": {
+   "Type": "AWS::SSM::Parameter::Value<AWS::EC2::Image::Id>",
+   "Default": "/aws/service/ami-windows-latest/Windows_Server-2022-English-Full-Base"
+  },
+  "BootstrapVersion": {
+   "Type": "AWS::SSM::Parameter::Value<String>",
+   "Default": "/cdk-bootstrap/hnb659fds/version",
+   "Description": "Version of the CDK Bootstrap resources in this environment, automatically retrieved from SSM Parameter Store. [cdk:skip]"
+  }
+ },
+ "Rules": {
+  "CheckBootstrapVersion": {
+   "Assertions": [
+    {
+     "Assert": {
+      "Fn::Not": [
+       {
+        "Fn::Contains": [
+         [
+          "1",
+          "2",
+          "3",
+          "4",
+          "5"
+         ],
+         {
+          "Ref": "BootstrapVersion"
+         }
+        ]
+       }
+      ]
+     },
+     "AssertDescription": "CDK bootstrap stack version 6 required. Please run 'cdk bootstrap' with a recent version of the CDK CLI."
+    }
+   ]
+  }
+ }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/manifest.json b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/manifest.json
new file mode 100644
index 0000000000000..c6246f95e2ec1
--- /dev/null
+++ b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/manifest.json
@@ -0,0 +1,226 @@
+{
+  "version": "21.0.0",
+  "artifacts": {
+    "Tree": {
+      "type": "cdk:tree",
+      "properties": {
+        "file": "tree.json"
+      }
+    },
+    "integ-userdata.assets": {
+      "type": "cdk:asset-manifest",
+      "properties": {
+        "file": "integ-userdata.assets.json",
+        "requiresBootstrapStackVersion": 6,
+        "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version"
+      }
+    },
+    "integ-userdata": {
+      "type": "aws:cloudformation:stack",
+      "environment": "aws://unknown-account/unknown-region",
+      "properties": {
+        "templateFile": "integ-userdata.template.json",
+        "validateOnSynth": false,
+        "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-deploy-role-${AWS::AccountId}-${AWS::Region}",
+        "cloudFormationExecutionRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-cfn-exec-role-${AWS::AccountId}-${AWS::Region}",
+        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/9f2c5f7def4ad32c13627dff08f2be0273546384a8fe510e265cc6a7083274e1.json",
+        "requiresBootstrapStackVersion": 6,
+        "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version",
+        "additionalDependencies": [
+          "integ-userdata.assets"
+        ],
+        "lookupRole": {
+          "arn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-lookup-role-${AWS::AccountId}-${AWS::Region}",
+          "requiresBootstrapStackVersion": 8,
+          "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version"
+        }
+      },
+      "dependencies": [
+        "integ-userdata.assets"
+      ],
+      "metadata": {
+        "/integ-userdata/IntegUserdataVpc/Resource": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcDE2938ED"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet1/Subnet": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet1/RouteTable": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet1RouteTable7B342D96"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet1/RouteTableAssociation": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet1RouteTableAssociation724A6375"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet1/DefaultRoute": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet1DefaultRoute8F93CC39"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet1/EIP": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet1EIP41DE8CA6"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet1/NATGateway": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet1NATGatewayC9F60940"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet2/Subnet": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet2Subnet7EC040B5"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet2/RouteTable": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet2RouteTable98BA8E97"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet2/RouteTableAssociation": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet2RouteTableAssociationBA5DC07F"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet2/DefaultRoute": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet2DefaultRoute90FCB645"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet2/EIP": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet2EIP662D51E3"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PublicSubnet2/NATGateway": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPublicSubnet2NATGatewayB25F84D3"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet1/Subnet": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet1Subnet4EFBF430"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet1/RouteTable": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet1RouteTable63E39754"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet1/RouteTableAssociation": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet1RouteTableAssociation176A5EB9"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet1/DefaultRoute": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet1DefaultRoute03370EF2"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet2/Subnet": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet2SubnetAFD1E5B4"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet2/RouteTable": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet2RouteTable7944CD08"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet2/RouteTableAssociation": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet2RouteTableAssociation3B0C1389"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/PrivateSubnet2/DefaultRoute": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcPrivateSubnet2DefaultRouteA120F4F4"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/IGW": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcIGWB657C40E"
+          }
+        ],
+        "/integ-userdata/IntegUserdataVpc/VPCGW": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "IntegUserdataVpcVPCGWFA86AC6A"
+          }
+        ],
+        "/integ-userdata/WindowsInstance/InstanceSecurityGroup/Resource": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "WindowsInstanceInstanceSecurityGroup3B6692A8"
+          }
+        ],
+        "/integ-userdata/WindowsInstance/InstanceRole/Resource": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "WindowsInstanceInstanceRoleB7D73766"
+          }
+        ],
+        "/integ-userdata/WindowsInstance/InstanceProfile": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "WindowsInstanceInstanceProfile20441977"
+          }
+        ],
+        "/integ-userdata/WindowsInstance/Resource": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "WindowsInstance4ABA347A"
+          }
+        ],
+        "/integ-userdata/SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118.Parameter": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "SsmParameterValueawsserviceamiwindowslatestWindowsServer2022EnglishFullBaseC96584B6F00A464EAD1953AFF4B05118Parameter"
+          }
+        ],
+        "/integ-userdata/BootstrapVersion": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "BootstrapVersion"
+          }
+        ],
+        "/integ-userdata/CheckBootstrapVersion": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "CheckBootstrapVersion"
+          }
+        ]
+      },
+      "displayName": "integ-userdata"
+    }
+  }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/tree.json b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/tree.json
new file mode 100644
index 0000000000000..b4e8cb0d210a0
--- /dev/null
+++ b/packages/@aws-cdk/aws-ec2/test/userdata.integ.snapshot/tree.json
@@ -0,0 +1,857 @@
+{
+  "version": "tree-0.1",
+  "tree": {
+    "id": "App",
+    "path": "",
+    "children": {
+      "Tree": {
+        "id": "Tree",
+        "path": "Tree",
+        "constructInfo": {
+          "fqn": "constructs.Construct",
+          "version": "10.1.108"
+        }
+      },
+      "integ-userdata": {
+        "id": "integ-userdata",
+        "path": "integ-userdata",
+        "children": {
+          "IntegUserdataVpc": {
+            "id": "IntegUserdataVpc",
+            "path": "integ-userdata/IntegUserdataVpc",
+            "children": {
+              "Resource": {
+                "id": "Resource",
+                "path": "integ-userdata/IntegUserdataVpc/Resource",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::EC2::VPC",
+                  "aws:cdk:cloudformation:props": {
+                    "cidrBlock": "10.0.0.0/16",
+                    "enableDnsHostnames": true,
+                    "enableDnsSupport": true,
+                    "instanceTenancy": "default",
+                    "tags": [
+                      {
+                        "key": "Name",
+                        "value": "integ-userdata/IntegUserdataVpc"
+                      }
+                    ]
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.CfnVPC",
+                  "version": "0.0.0"
+                }
+              },
+              "PublicSubnet1": {
+                "id": "PublicSubnet1",
+                "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1",
+                "children": {
+                  "Subnet": {
+                    "id": "Subnet",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/Subnet",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Subnet",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "availabilityZone": {
+                          "Fn::Select": [
+                            0,
+                            {
+                              "Fn::GetAZs": ""
+                            }
+                          ]
+                        },
+                        "cidrBlock": "10.0.0.0/18",
+                        "mapPublicIpOnLaunch": true,
+                        "tags": [
+                          {
+                            "key": "aws-cdk:subnet-name",
+                            "value": "Public"
+                          },
+                          {
+                            "key": "aws-cdk:subnet-type",
+                            "value": "Public"
+                          },
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnet",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "Acl": {
+                    "id": "Acl",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/Acl",
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTable": {
+                    "id": "RouteTable",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/RouteTable",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::RouteTable",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRouteTable",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTableAssociation": {
+                    "id": "RouteTableAssociation",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/RouteTableAssociation",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::SubnetRouteTableAssociation",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet1RouteTable7B342D96"
+                        },
+                        "subnetId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnetRouteTableAssociation",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "DefaultRoute": {
+                    "id": "DefaultRoute",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/DefaultRoute",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Route",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet1RouteTable7B342D96"
+                        },
+                        "destinationCidrBlock": "0.0.0.0/0",
+                        "gatewayId": {
+                          "Ref": "IntegUserdataVpcIGWB657C40E"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRoute",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "EIP": {
+                    "id": "EIP",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/EIP",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::EIP",
+                      "aws:cdk:cloudformation:props": {
+                        "domain": "vpc",
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnEIP",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "NATGateway": {
+                    "id": "NATGateway",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet1/NATGateway",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::NatGateway",
+                      "aws:cdk:cloudformation:props": {
+                        "subnetId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+                        },
+                        "allocationId": {
+                          "Fn::GetAtt": [
+                            "IntegUserdataVpcPublicSubnet1EIP41DE8CA6",
+                            "AllocationId"
+                          ]
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet1"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnNatGateway",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.PublicSubnet",
+                  "version": "0.0.0"
+                }
+              },
+              "PublicSubnet2": {
+                "id": "PublicSubnet2",
+                "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2",
+                "children": {
+                  "Subnet": {
+                    "id": "Subnet",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/Subnet",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Subnet",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "availabilityZone": {
+                          "Fn::Select": [
+                            1,
+                            {
+                              "Fn::GetAZs": ""
+                            }
+                          ]
+                        },
+                        "cidrBlock": "10.0.64.0/18",
+                        "mapPublicIpOnLaunch": true,
+                        "tags": [
+                          {
+                            "key": "aws-cdk:subnet-name",
+                            "value": "Public"
+                          },
+                          {
+                            "key": "aws-cdk:subnet-type",
+                            "value": "Public"
+                          },
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnet",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "Acl": {
+                    "id": "Acl",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/Acl",
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTable": {
+                    "id": "RouteTable",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/RouteTable",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::RouteTable",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRouteTable",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTableAssociation": {
+                    "id": "RouteTableAssociation",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/RouteTableAssociation",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::SubnetRouteTableAssociation",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet2RouteTable98BA8E97"
+                        },
+                        "subnetId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet2Subnet7EC040B5"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnetRouteTableAssociation",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "DefaultRoute": {
+                    "id": "DefaultRoute",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/DefaultRoute",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Route",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet2RouteTable98BA8E97"
+                        },
+                        "destinationCidrBlock": "0.0.0.0/0",
+                        "gatewayId": {
+                          "Ref": "IntegUserdataVpcIGWB657C40E"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRoute",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "EIP": {
+                    "id": "EIP",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/EIP",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::EIP",
+                      "aws:cdk:cloudformation:props": {
+                        "domain": "vpc",
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnEIP",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "NATGateway": {
+                    "id": "NATGateway",
+                    "path": "integ-userdata/IntegUserdataVpc/PublicSubnet2/NATGateway",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::NatGateway",
+                      "aws:cdk:cloudformation:props": {
+                        "subnetId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet2Subnet7EC040B5"
+                        },
+                        "allocationId": {
+                          "Fn::GetAtt": [
+                            "IntegUserdataVpcPublicSubnet2EIP662D51E3",
+                            "AllocationId"
+                          ]
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PublicSubnet2"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnNatGateway",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.PublicSubnet",
+                  "version": "0.0.0"
+                }
+              },
+              "PrivateSubnet1": {
+                "id": "PrivateSubnet1",
+                "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet1",
+                "children": {
+                  "Subnet": {
+                    "id": "Subnet",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet1/Subnet",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Subnet",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "availabilityZone": {
+                          "Fn::Select": [
+                            0,
+                            {
+                              "Fn::GetAZs": ""
+                            }
+                          ]
+                        },
+                        "cidrBlock": "10.0.128.0/18",
+                        "mapPublicIpOnLaunch": false,
+                        "tags": [
+                          {
+                            "key": "aws-cdk:subnet-name",
+                            "value": "Private"
+                          },
+                          {
+                            "key": "aws-cdk:subnet-type",
+                            "value": "Private"
+                          },
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PrivateSubnet1"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnet",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "Acl": {
+                    "id": "Acl",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet1/Acl",
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTable": {
+                    "id": "RouteTable",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet1/RouteTable",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::RouteTable",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PrivateSubnet1"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRouteTable",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTableAssociation": {
+                    "id": "RouteTableAssociation",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet1/RouteTableAssociation",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::SubnetRouteTableAssociation",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPrivateSubnet1RouteTable63E39754"
+                        },
+                        "subnetId": {
+                          "Ref": "IntegUserdataVpcPrivateSubnet1Subnet4EFBF430"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnetRouteTableAssociation",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "DefaultRoute": {
+                    "id": "DefaultRoute",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet1/DefaultRoute",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Route",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPrivateSubnet1RouteTable63E39754"
+                        },
+                        "destinationCidrBlock": "0.0.0.0/0",
+                        "natGatewayId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet1NATGatewayC9F60940"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRoute",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.PrivateSubnet",
+                  "version": "0.0.0"
+                }
+              },
+              "PrivateSubnet2": {
+                "id": "PrivateSubnet2",
+                "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet2",
+                "children": {
+                  "Subnet": {
+                    "id": "Subnet",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet2/Subnet",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Subnet",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "availabilityZone": {
+                          "Fn::Select": [
+                            1,
+                            {
+                              "Fn::GetAZs": ""
+                            }
+                          ]
+                        },
+                        "cidrBlock": "10.0.192.0/18",
+                        "mapPublicIpOnLaunch": false,
+                        "tags": [
+                          {
+                            "key": "aws-cdk:subnet-name",
+                            "value": "Private"
+                          },
+                          {
+                            "key": "aws-cdk:subnet-type",
+                            "value": "Private"
+                          },
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PrivateSubnet2"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnet",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "Acl": {
+                    "id": "Acl",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet2/Acl",
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/core.Resource",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTable": {
+                    "id": "RouteTable",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet2/RouteTable",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::RouteTable",
+                      "aws:cdk:cloudformation:props": {
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/IntegUserdataVpc/PrivateSubnet2"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRouteTable",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "RouteTableAssociation": {
+                    "id": "RouteTableAssociation",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet2/RouteTableAssociation",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::SubnetRouteTableAssociation",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPrivateSubnet2RouteTable7944CD08"
+                        },
+                        "subnetId": {
+                          "Ref": "IntegUserdataVpcPrivateSubnet2SubnetAFD1E5B4"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSubnetRouteTableAssociation",
+                      "version": "0.0.0"
+                    }
+                  },
+                  "DefaultRoute": {
+                    "id": "DefaultRoute",
+                    "path": "integ-userdata/IntegUserdataVpc/PrivateSubnet2/DefaultRoute",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::Route",
+                      "aws:cdk:cloudformation:props": {
+                        "routeTableId": {
+                          "Ref": "IntegUserdataVpcPrivateSubnet2RouteTable7944CD08"
+                        },
+                        "destinationCidrBlock": "0.0.0.0/0",
+                        "natGatewayId": {
+                          "Ref": "IntegUserdataVpcPublicSubnet2NATGatewayB25F84D3"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnRoute",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.PrivateSubnet",
+                  "version": "0.0.0"
+                }
+              },
+              "IGW": {
+                "id": "IGW",
+                "path": "integ-userdata/IntegUserdataVpc/IGW",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::EC2::InternetGateway",
+                  "aws:cdk:cloudformation:props": {
+                    "tags": [
+                      {
+                        "key": "Name",
+                        "value": "integ-userdata/IntegUserdataVpc"
+                      }
+                    ]
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.CfnInternetGateway",
+                  "version": "0.0.0"
+                }
+              },
+              "VPCGW": {
+                "id": "VPCGW",
+                "path": "integ-userdata/IntegUserdataVpc/VPCGW",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::EC2::VPCGatewayAttachment",
+                  "aws:cdk:cloudformation:props": {
+                    "vpcId": {
+                      "Ref": "IntegUserdataVpcDE2938ED"
+                    },
+                    "internetGatewayId": {
+                      "Ref": "IntegUserdataVpcIGWB657C40E"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.CfnVPCGatewayAttachment",
+                  "version": "0.0.0"
+                }
+              }
+            },
+            "constructInfo": {
+              "fqn": "@aws-cdk/aws-ec2.Vpc",
+              "version": "0.0.0"
+            }
+          },
+          "WindowsInstance": {
+            "id": "WindowsInstance",
+            "path": "integ-userdata/WindowsInstance",
+            "children": {
+              "InstanceSecurityGroup": {
+                "id": "InstanceSecurityGroup",
+                "path": "integ-userdata/WindowsInstance/InstanceSecurityGroup",
+                "children": {
+                  "Resource": {
+                    "id": "Resource",
+                    "path": "integ-userdata/WindowsInstance/InstanceSecurityGroup/Resource",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::EC2::SecurityGroup",
+                      "aws:cdk:cloudformation:props": {
+                        "groupDescription": "integ-userdata/WindowsInstance/InstanceSecurityGroup",
+                        "securityGroupEgress": [
+                          {
+                            "cidrIp": "0.0.0.0/0",
+                            "description": "Allow all outbound traffic by default",
+                            "ipProtocol": "-1"
+                          }
+                        ],
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/WindowsInstance"
+                          }
+                        ],
+                        "vpcId": {
+                          "Ref": "IntegUserdataVpcDE2938ED"
+                        }
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-ec2.CfnSecurityGroup",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.SecurityGroup",
+                  "version": "0.0.0"
+                }
+              },
+              "InstanceRole": {
+                "id": "InstanceRole",
+                "path": "integ-userdata/WindowsInstance/InstanceRole",
+                "children": {
+                  "Resource": {
+                    "id": "Resource",
+                    "path": "integ-userdata/WindowsInstance/InstanceRole/Resource",
+                    "attributes": {
+                      "aws:cdk:cloudformation:type": "AWS::IAM::Role",
+                      "aws:cdk:cloudformation:props": {
+                        "assumeRolePolicyDocument": {
+                          "Statement": [
+                            {
+                              "Action": "sts:AssumeRole",
+                              "Effect": "Allow",
+                              "Principal": {
+                                "Service": {
+                                  "Fn::Join": [
+                                    "",
+                                    [
+                                      "ec2.",
+                                      {
+                                        "Ref": "AWS::URLSuffix"
+                                      }
+                                    ]
+                                  ]
+                                }
+                              }
+                            }
+                          ],
+                          "Version": "2012-10-17"
+                        },
+                        "tags": [
+                          {
+                            "key": "Name",
+                            "value": "integ-userdata/WindowsInstance"
+                          }
+                        ]
+                      }
+                    },
+                    "constructInfo": {
+                      "fqn": "@aws-cdk/aws-iam.CfnRole",
+                      "version": "0.0.0"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-iam.Role",
+                  "version": "0.0.0"
+                }
+              },
+              "InstanceProfile": {
+                "id": "InstanceProfile",
+                "path": "integ-userdata/WindowsInstance/InstanceProfile",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::IAM::InstanceProfile",
+                  "aws:cdk:cloudformation:props": {
+                    "roles": [
+                      {
+                        "Ref": "WindowsInstanceInstanceRoleB7D73766"
+                      }
+                    ]
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-iam.CfnInstanceProfile",
+                  "version": "0.0.0"
+                }
+              },
+              "Resource": {
+                "id": "Resource",
+                "path": "integ-userdata/WindowsInstance/Resource",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::EC2::Instance",
+                  "aws:cdk:cloudformation:props": {
+                    "availabilityZone": {
+                      "Fn::Select": [
+                        0,
+                        {
+                          "Fn::GetAZs": ""
+                        }
+                      ]
+                    },
+                    "iamInstanceProfile": {
+                      "Ref": "WindowsInstanceInstanceProfile20441977"
+                    },
+                    "imageId": {
+                      "Ref": "SsmParameterValueawsserviceamiwindowslatestWindowsServer2022EnglishFullBaseC96584B6F00A464EAD1953AFF4B05118Parameter"
+                    },
+                    "instanceType": "t2.micro",
+                    "securityGroupIds": [
+                      {
+                        "Fn::GetAtt": [
+                          "WindowsInstanceInstanceSecurityGroup3B6692A8",
+                          "GroupId"
+                        ]
+                      }
+                    ],
+                    "subnetId": {
+                      "Ref": "IntegUserdataVpcPublicSubnet1Subnet9AE7FE85"
+                    },
+                    "tags": [
+                      {
+                        "key": "Name",
+                        "value": "integ-userdata/WindowsInstance"
+                      }
+                    ],
+                    "userData": {
+                      "Fn::Base64": "<powershell></powershell><persist>true</persist>"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-ec2.CfnInstance",
+                  "version": "0.0.0"
+                }
+              }
+            },
+            "constructInfo": {
+              "fqn": "@aws-cdk/aws-ec2.Instance",
+              "version": "0.0.0"
+            }
+          },
+          "SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118.Parameter": {
+            "id": "SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118.Parameter",
+            "path": "integ-userdata/SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118.Parameter",
+            "constructInfo": {
+              "fqn": "@aws-cdk/core.CfnParameter",
+              "version": "0.0.0"
+            }
+          },
+          "SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118": {
+            "id": "SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118",
+            "path": "integ-userdata/SsmParameterValue:--aws--service--ami-windows-latest--Windows_Server-2022-English-Full-Base:C96584B6-F00A-464E-AD19-53AFF4B05118",
+            "constructInfo": {
+              "fqn": "@aws-cdk/core.Resource",
+              "version": "0.0.0"
+            }
+          }
+        },
+        "constructInfo": {
+          "fqn": "@aws-cdk/core.Stack",
+          "version": "0.0.0"
+        }
+      }
+    },
+    "constructInfo": {
+      "fqn": "@aws-cdk/core.App",
+      "version": "0.0.0"
+    }
+  }
+}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-ec2/test/userdata.test.ts b/packages/@aws-cdk/aws-ec2/test/userdata.test.ts
index fc877cbb2c7c9..4a29db3ea45c9 100644
--- a/packages/@aws-cdk/aws-ec2/test/userdata.test.ts
+++ b/packages/@aws-cdk/aws-ec2/test/userdata.test.ts
@@ -178,6 +178,14 @@ describe('user data', () => {
     );
 
   });
+  test('can persist windows userdata', () => {
+    // WHEN
+    const userData = ec2.UserData.forWindows({ persist: true });
+
+    // THEN
+    const rendered = userData.render();
+    expect(rendered).toEqual('<powershell></powershell><persist>true</persist>');
+  });
   test('can create Linux user data', () => {
     // GIVEN