Configuring AWS Systems Manager for use with VMware Cloud on AWS

Maintaining tight access control for workloads and ensuring they are on the latest patch revisions is central to running an efficient and secure IT environment. In this post we cover how to heighten security by leveraging the tools which comes with AWS Systems Manager and complementing AWS native services. This way IT administrators will be empowered with tools central to their quest of reaching higher security levels while simultaneously being able to reduce management overhead

This post is also available on AWS Re-post here:–pQSKwWteAIdpktw

Integrating AWS Systems Manager (SSM) with VMware Cloud on AWS

Deploying SSM can help enhance security for both cloud native and VMware Cloud on AWS environments. This post will show how to integrate SSM with VMware Cloud on AWS for secure remote access as well as security patching of VMs.

Detailed configuration steps are covered below, but the main points are:

  • Enabling and performing initial SSM configuration
  • Creating a VPC endpoint for SSM in the VMware Cloud on AWS connected VPC
  • Creating an inbound endpoint for Route 53
  • Install the SSM agent and registering the VMs with SSM

The SSM endpoint gives the VMs a private IP to communicate with SSM and the Route 53 inbound endpoint ensures that the VMs receive that private IP when they resolve the SSM FQDN. Without these two endpoints the VMs would communicate with SSM over the internet.


Integrating AWS Systems Manager with VMware Cloud on AWS is relatively straightforward. While AWS SSM comes with public endpoints for VM-to-SSM communication, the preferred way is to use private IP addressing over the connected VPC Elastic Network Interface (ENI). To accomplish this, create an SSM endpoint in the connected VPC and then set the networks on the VMware Cloud on AWS SDDC CGW to use a Route 53 inbound resolver. That way any communication the SSM agent does to the regional SSM endpoint will go over the ENI rather than the internet. No changes on the VMs are required apart from ensuring they use the correct Route 53 DNS resolver.

Overall network architecture for AWS Systems Manager integration with VMware Cloud on AWS

Integrating AWS Systems Manager for the VMware Cloud on AWS environment involves creating an SSM endpoint in the customer connected VPC and adding a DNS inbound endpoint

Full diagram:

Configuration steps

In this section the practical setup of AWS Systems Manager with VMware Cloud on AWS is covered. General guidelines for getting started with AWS Systems Manager is covered in the SSM User Guide. The steps below are VMware and VMware Cloud on AWS specific and aim to get an environment up and running swiftly.

Overview of steps involved in setting up Systems Manager for use with VMware Cloud on AWS

  1. Setting the systems manager region
  2. Creating an S3 bucket for SSM logs and inventory output
  3. Creating the S3 bucket policy in IAM
  4. Creating the systems manager IAM users
  5. Creating the systems manager VPC endpoints
  6. Creating the R53 DNS inbound endpoint
  7. Pointing CGW DNS to R53
  8. Creating the SDDC firewall rules
  9. Creating a hybrid activation
  10. VM configuration: Installing the SSM agent and registering with SSM

1. Setting the systems manager region and enable Advanced-Tier

AWS Systems Manager is bound to a region of choice when activated the first time. Please pick a region which makes sense to your organization and note that it cannot be changed afterwards. For a VMware Cloud on AWS environment this would usually be the same region as the VMware Cloud on AWS environment is deployed in.

The easiest way to set the region is to go to AWS Systems Manager Quick Start and select your preferred region during the setup. Access AWS Systems Manager Console here: Also refer to the AWS Systems Manager getting started guide here:

To use advanced features of AWS SSM, like patch management of VMware VMs, Advanced-Tier has to be enabled. This will incur an extra charge for instance management. At the time of writing the daily cost for one instance would be $0.1668 USD. Please refer to the SSM pricing structure for more detail and up-to-date pricing.

Once AWS SSM has been set to your preferred region, access “Fleet Manager” and under “Account management” select to modify the settings for Instance tiers.

Under the “Instance tier settings” confirm change from Standard-Tier to Advanced-Tier

2. Creating an S3 bucket for SSM logs and inventory output

Having a designated S3 bucket for SSM logs and other output, like inventory data, makes administration easier. The output can later be accessed for tracking, troubleshooting or even for access via Athena where inventory data can be formatted using SQL queries and used in QuickSight reports.

3. Creating the S3 bucket policy in IAM

The S3 bucket created in step 2 need a policy to allow SSM to access it. This policy will be created in IAM and then attached to the IAM roles used in both cloud native and VMware Cloud on AWS environments. Note that while this is a policy for S3 access, it is created in IAM and not in the S3 console.

The policy is created based on the JSON document below. Please update “YOUR-REGION” and “YOUR-BUCKET-NAME” with the relevant values for your environment.

    "Version": "2012-10-17",
    "Statement": [
            "Effect": "Allow",
            "Action": "s3:GetObject",
            "Resource": [
            "Effect": "Allow",
            "Action": [
            "Resource": [

4. Creating the systems manager IAM roles

AWS Systems Manager can cover the management of both EC2 instances as well as VMware Cloud on AWS VMs. Each of these instance / VM types require a role created for them in IAM. This is to give the instance / VM the ability to interact with SSM and vice-versa. Detailed steps for this is covered in the AWS SSM user guide. In this section we will cover how to quickly get the VMware Cloud on AWS VM role created for use with hybrid activations in SSM.

Navigate to IAM in the AWS Console and create a new role. Select “Trusted entity type” to be “AWS Service” and the “Use Case” to be “Systems Manager”.

Under Permissions, search for and select the following:

  • CloudWatchAgentServerPolicy
  • AmazonSSMDirectoryServiceAccess
  • AmazonSSMManagedInstanceCore
  • The policy previously created for the SSM S3 bucket

5. Creating the systems manager VPC endpoints

Endpoints for AWS SSM can be created in the VMware Cloud on AWS Connected VPC. This is to provide the VMs in VMware Cloud on AWS a path to communicate with AWS SSM via the connected VPC ENI rather than accessing AWS SSM over the internet. This is both secure and as long as the SSM endpoint in the connected VPC is in the same availability zone as the VMware Cloud on AWS SDDC, communication is free of charge.

Create endpoints for the SSM service and, optionally, also KMS, Logs and SSM messages services as per the below:

6. Creating the R53 DNS inbound endpoint

Creating the SSM endpoint is the first step but the VMs in VMware Cloud on AWS must also be directed to that endpoint rather than the public SSM IP addresses. Rather than modifying each VM, a more efficient way is to add a Route 53 inbound endpoint to the Connected VPC. If the CGW DHCP server for the VMware Cloud on AWS VM segments is then updated to point DNS to that Route 53 endpoint, the VMs will automatically resolve the SSM FQDN to the endpoint private IP address.

Make sure that the security group for the inbound R53 endpoints allow DNS on both TCP and UDP from the VMware Cloud on AWS CGW network segments.

7. Pointing CGW DNS to R53

In the VMware Cloud on AWS console, navigate to “Networking & Security” and select “Segments” under Network. Update the network segments for the VMs to use the R53 inbound endpoint IP addresses.

The VMs connected to the CGW network segment may need to be disconnected and then re-connected to the network in vCenter or restart the networking from the OS side for the changes to take effect.

Before changing the DNS to point to the R53 inbound endpoint the VM in VMware Cloud on AWS resolves the regional SSM endpoint to the public IP address. Communication is done via the IGW in the VMware Cloud on AWS environment.

After updating the DNS the VM resolves the SSM endpoint to the private endpoint created earlier. Communication is over the Connected VPC ENI. Note: The ping doesn’t succeed since the security group for SSM blocks ICMP. However, the command shows that the VM correctly resolves the regional SSM endpoint to the private IP address in the Connected VPC.

8. Creating the SDDC firewall rules

The network segments connected to the VMware Cloud on AWS CGW router need access to both SSM and R53 services in the Connected VPC. AWS SSM also need to be able to access the VMware Cloud on AWS VMs over the Connected VPC ENI. Create firewall rules on the CGW to allow this traffic. In the screenshot below the VMware Cloud on AWS VM network “cgw-53” is allowed to communicate anywhere over any uplink while inbound traffic to the same network is allowed over the VPC interface only.

9. Creating a hybrid activation

Virtual machines external to EC2 are added to AWS SSM through a “Hybrid activation”. This is created via the SSM section of the AWS Console and generates an ID and a code for a preset number of VMs. These can be used as credentials in the next step where the SSM agent is installed and the VMs are registered with SSM

10. VM configuration: Installing the SSM agent and registering with SSM

Instances on EC2 normally come with the SSM agent pre-installed. For VMs in VMware Cloud on AWS or on-premises VMware environments the agent needs to be installed. This is both quick and easy to do. The details for agent installation for a multitude of OS types are described in the SSM user guide. In this example the agent will be installed on a Linux VM. Instructions for Windows VMs can be found here.

After downloading and installing the agent, the Hybrid Activation code and ID from step 9 above are used to register the VM with AWS SSM

Verifying that the VM is available in Systems Manager. Note that in contrast from EC2 instances, the VMware Cloud on AWS VM is prefixed with an “mi-” rather than just an “i-”. This is an indication it is a Managed Instance external to EC2. Of course labels and groups can also be used to keep the managed nodes apart, but the Node ID is a quick indicator of where it comes from.

Managing the VMs in Systems Manager

Viewing the VM inventory

Once the AWS SSM agent is installed it will start collecting the software inventory of the VM. This data is available through the SSM Inventory console but can also be exported to S3 for further processing by Athena. Detailed reports can be created by pointing QuickSight to the Athena data.

Accessing VM registry, logs and filesystem

The VM filesystem, performance metrics, system logs and even registry for Windows VMs is accessible directly through the AWS Console for each VM registered with SSM. Administering the VMs though the AWS Console reduces the need for direct desktop or shell access. For some features, like performance metrics, please be sure to enable KMS encryption in the SSM general settings.

Accessing the VM PowerShell console

While PowerShell or a shell prompt on a VM can be accessed over RDP or SSH, having the ability to quickly connect to a VM console through SSM helps streamline system administration.

Accessing the VM desktop

For Windows VMs it is possible to quickly open an RDP session even though the firewall on the VM is enabled and blocking RDP. The SSM agent creates a loopback connection which enables access from the AWS console. Up to four sessions can be opened in a single SSM Session Manager window. The session window can be maximized to view the VM in full screen

Patching VMs

Through SSM Patch manager, patch baselines and maintenance windows can easily be created and applied to the managed VMware VMs as well as EC2 instances to ensure they are up to date and have the highest level of protection possible


VMware Cloud on AWS is not a standalone solution but integrates well with a variety of AWS native services. In this blog post AWS Systems Manager and related services were leveraged to enhance security of VMs running on VMware Cloud on AWS by centralizing access controls and automating OS patch management.

Further reading

New blog post for migrating from on-premises VMware vSphere to VMware Cloud on AWS using FSx for NetApp ONTAP SnapMirror

Recently published blog post showing the pros and cons for migrating virtual machines using SnapMirror and also some ideas about how to use a similar methodology for disaster recovery purposes

Access the blog on the AWS official web page here:

Tutorial for deploying and configuring VMware HCX in both on-premises and VMware Cloud on AWS with service mesh creation and L2 extension

Deploying HCX (VMware Hybrid Cloud Extensions) is considered to be complex and difficult by most. It doesn’t help that it’s usually one of those things you’d only do once so it doesn’t pay to spend a lot of effort to learn. However, as with everything it’s not hard once you know how to do it. This video aims to show how to deploy HCX both in VMC (VMware Cloud on AWS) and in the on-premises DC or lab.

It uses both the method of creating the service mesh over the internet as well as how to create it over a private connection, like DX (AWS Direct Connect) or a VPN.

A VPN cannot be used for L2 Extension if it is terminated on the VMC SDDC. In this tutorial I’ll use a VPN which is terminated on an AWS TGW which is in turn peered with a VTGW connected to the SDDC we’re attaching to.

Video chapters

  1. Switching vCenter to private IP and deploying HCX Cloud in VMC:
  2. Initial SDDC firewall configuration:
  3. Switching HCX to private IP and adding HCX firewall rules:
  4. Downloading and deploying HCX for the on-prem DC side:
  5. Adding HCX license, linking on-prem HCX with vCenter:
  6. HCX site pairing between HCX Connector and HCX Cloud:
  7. Creating HCX Network and Compute profiles:
  8. Choice: Deploy service mesh over public IP or private IP:
  9. Deploy service mesh over public IP:
  10. Live migrating a VM to AWS:
  11. Deploy service mesh over private IP (DX, VPN to TGW):

Some architecture diagrams for reference

Connecting all over the public internet is one method
The best performance may be had over a dedicated DX Private VIF to the SDDC
Separating the management traffic over a VPN while doing the L2 Extension over the internet is a bit of a hybrid
For the setup used in the tutorial I use a VPN to a TGW which is peered with a VTGW

Migrate VMware VMs from an on-prem DC to VMware Cloud on AWS (VMC) using Veeam Backup and Replication

When migrating from an on-premises DC to VMware Cloud on AWS it is usually recommended to use Hybrid Cloud Extension (HCX) from VMware. However, in some cases the IT team managing the on-prem DC is already using Veeam for backup and want to use their solution also for the migration.

They may also prefer Veeam over HCX as HCX often requires professional services assistance for setup and migration planning. In addition, since HCX is primarily a tool for migrations, the customer is unlikely to have had experience setting it up in the past and while it is an excellent tool there is a learning curve to get started.

Migrating with Veeam vs. Migrating with HCX

Veeam Backup & RecoveryVMware Hybrid Cloud Extension (HCX)
Licensed (non-free) solutionFree with VMware Cloud on AWS
Arguably easy to set up and configureArguably challenging to set up and configure
Can do offline migrations of VMs, single or in bulkCan do online migrations (no downtime), offline migrations, bulk migrations and online migrations in bulk (RAV), etc.
Can not do L2 extensionCan do L2 extension of VLANs if they are connected to a vDS
Can be used for backup of VMs after they have been migratedIs primarily used for migration. Does not have backup functionality
Support for migrating from older on-prem vSphere environmentsAt time of writing, full support for on-prem vSphere 6.5 or newer. Limited support for vSphere 6.0 up to March 12th 2023

What we are building

This guide covers installing and configuring a single Veeam Backup and Recovery installation in the on-prem VMware environment and linking it to both vCenter on-prem as well as in VMware Cloud on AWS. Finally we do an offline migration of a VM to the cloud to prove it that it works.


The guide assumes the following is already set up and available

  • On-premises vSphere environment with admin access (7.0 used in this example)
  • Windows Server VM to be used for Veeam install
    • Min spec here
    • Windows Server 2019 was used for this guide
    • Note: I initially used 2 vCPU, 4GB RAM and 60 GB HDD for my Veeam VM but during the first migration the entire thing stalled and wouldn’t finish. After changing to 4 vCPU, 32Gb RAM and 170 GB HDD the migration finished quickly and with no errors. Recommend to assign as much resources as is practical to the Veeam VM to facilitate and speed up the migration
  • One VMware Cloud on AWS (VMC) Software Defined Datacenter (SDDC)
  • Private IP connectivity to the VMC SDDC
    • Use Direct Connect (DX) or VPN but it must be private IP connectivity or it won’t work
    • For this setup I used a VPN to a TGW, then a peering to a VMware Transit Connect (VTGW) which had an attachment to the SDDC, but any private connectivity setup will be OK
  • A test VM to use for migration

Downloading and installing Veeam

Unless you already have a licensed copy, sign up for a trial license and then download Veeam Backup and Recovery from here. Version used in this guide.

In your on-premises vSphere environment, create or select a Windows Server VM to use for the Veeam installation. The VM spec used for this install are as follows:

Run the install with default settings (next, next, next, etc.)

Register the on-prem vCenter in Veeam

Navigate to “Inventory” at the bottom left, then “Virtual Infrastructure” and click “Add Server” to register the on-prem vCenter server

Listing VMs in the on-prem vSphere environment after the vCenter server has been registered in the Veeam Backup & Recovery console

Switching on-prem connectivity to VMware Cloud on AWS SDDC to use private IP addresses

For this setup there is a VPN from the on-premises DC to the SDDC (via a TGW and VTGW in this case) but the SDDC FQDN is still configured to return the public IP address. Let’s verify by pinging the FQDN

Switching the SDDC to return the private IP is easy. In the VMware Cloud on AWS web console, navigate to “Settings” and flip the IP to return from public to private

Ping the vCenter FQDN again to verify that private IP is returned by DNS and that we can ping it successfully over the VPN

All looks good. The private IP is returned. Time to register the VMware Cloud on AWS vCenter instance in the Veeam console

Registering the VMC vCenter instance with Veeam

Just use the same method as used when adding the on-premises vCenter server: Navigate to “Inventory” at the bottom left, then “Virtual Infrastructure” and click “Add Server” to register the on-prem vCenter server with Veeam

Note: If the SDDC vCenter had not been switched to use a private IP there will be an error in listing the data stores. Subsequently when migrating a VM the target data store won’t be listed and the migration can’t be started

After adding the VMware Cloud on AWS SDDC vCenter the resource pools will be visible in the Veeam console

Now both vSphere environments are registered. Time to migrate a VM to the cloud!

Migrating a VM to VMware Cloud on AWS

Below is both a video and a series of screenshots describing the migration / replication job creation for the VM.

Creating some test files on the source VM to be migrated

Navigate to “Inventory” using the bottom left menu, click the on-premises vCenter server / Cluster and locate a VM to migrate in the on-premises DC VM inventory. Right-click the VM to migrate and create a replication job

When selecting the target for the replication, be sure to expand the VMware cloud on AWS cluster and select one of the ESXi servers. Selecting the cluster is not enough to list up the required resources, like storage volumes

Since VMC is a managed environment we want to select the customer-side of the storage, folder and resource pools

If you checked the box for remapping the network is even possible to select a target VLAN for the VM to be connected to on the cloud side!

Select to start the “Run the job when I click finish” and move to the “Home” tab to view the “Running jobs”

The migration of the test VM finished in less than 9 minutes

In the vCenter client for VMware Cloud on AWS we can verify that the replicated VM is present

After logging in and listing the files we can verify that the VM is not only working but also have the test files present in the home directory

Thank you for reading! Hopefully this has provided an easy-to-understand summary of the steps required for a successful migration / replication of VMs to VMC using Veeam