diff --git a/enos/enos-scenario-e2e-aws-windows.hcl b/enos/enos-scenario-e2e-aws-rdp-base.hcl
similarity index 92%
rename from enos/enos-scenario-e2e-aws-windows.hcl
rename to enos/enos-scenario-e2e-aws-rdp-base.hcl
index eed9b49c23..5cc974d759 100644
--- a/enos/enos-scenario-e2e-aws-windows.hcl
+++ b/enos/enos-scenario-e2e-aws-rdp-base.hcl
@@ -1,7 +1,11 @@
 # Copyright (c) HashiCorp, Inc.
 # SPDX-License-Identifier: BUSL-1.1
 
-scenario "e2e_aws_windows" {
+# This scenario creates a complete end-to-end test environment for Boundary to
+# test RDP functionality. It includes a Windows client, a Boundary controller
+# and worker, a domain controller, a member server, and another member server
+# with a worker running on it.
+scenario "e2e_aws_rdp_base" {
   terraform_cli = terraform_cli.default
   terraform     = terraform.default
   providers = [
@@ -10,8 +14,11 @@ scenario "e2e_aws_windows" {
   ]
 
   matrix {
-    builder    = ["local", "crt"]
-    client     = ["win10", "win11"]
+    builder = ["local", "crt"]
+    client  = ["win10", "win11"]
+    # Windows Server 2016 does not support OpenSSH, but it's relied on for some
+    # parts of setup. If 2016 is selected, the member server will be created as
+    # 2016, but the domain controller and worker will be 2019.
     rdp_server = ["2016", "2019", "2022", "2025"]
   }
 
@@ -150,7 +157,7 @@ scenario "e2e_aws_windows" {
 
     variables {
       vpc_id         = step.create_base_infra.vpc_id
-      server_version = matrix.rdp_server
+      server_version = matrix.rdp_server == "2016" ? "2019" : matrix.rdp_server
     }
   }
 
@@ -233,7 +240,7 @@ scenario "e2e_aws_windows" {
 
     variables {
       vpc_id                              = step.create_base_infra.vpc_id
-      server_version                      = matrix.rdp_server
+      server_version                      = matrix.rdp_server == "2016" ? "2019" : matrix.rdp_server
       boundary_cli_zip_path               = step.build_boundary_windows.artifact_path
       kms_key_arn                         = step.create_base_infra.kms_key_arn
       controller_ip                       = step.create_boundary_cluster.public_controller_addresses[0]
@@ -245,6 +252,7 @@ scenario "e2e_aws_windows" {
       domain_admin_password               = step.create_rdp_domain_controller.password
       domain_controller_private_key       = step.create_rdp_domain_controller.ssh_private_key
       domain_controller_sec_group_id_list = step.create_rdp_domain_controller.security_group_id_list
+      aws_region                          = var.aws_region
     }
   }
 
@@ -303,6 +311,9 @@ scenario "e2e_aws_windows" {
       client_username                          = step.create_windows_client.test_username
       client_password                          = step.create_windows_client.test_password
       client_test_dir                          = step.create_windows_client.test_dir
+      vault_addr_public                        = step.create_vault_cluster.instance_public_ips_ipv4[0]
+      vault_addr_private                       = step.create_vault_cluster.instance_private_ips[0]
+      vault_root_token                         = step.create_vault_cluster.vault_root_token
     }
   }
 
@@ -389,4 +400,4 @@ scenario "e2e_aws_windows" {
   output "windows_worker_private_ip" {
     value = step.create_windows_worker.private_ip
   }
-}
\ No newline at end of file
+}
diff --git a/enos/enos-scenario-e2e-aws-rdp-target.hcl b/enos/enos-scenario-e2e-aws-rdp-target.hcl
index 04fbf3f531..1393329c61 100644
--- a/enos/enos-scenario-e2e-aws-rdp-target.hcl
+++ b/enos/enos-scenario-e2e-aws-rdp-target.hcl
@@ -1,6 +1,8 @@
 # Copyright (c) HashiCorp, Inc.
 # SPDX-License-Identifier: BUSL-1.1
 
+# This scenario creates a single Windows ec2 instance that acts as a domain
+# controller. This can be used as an RDP target for boundary.
 scenario "e2e_aws_rdp_target" {
   terraform_cli = terraform_cli.default
   terraform     = terraform.default
diff --git a/enos/modules/aws_rdp_member_server/main.tf b/enos/modules/aws_rdp_member_server/main.tf
index d231460c56..128b7883f8 100644
--- a/enos/modules/aws_rdp_member_server/main.tf
+++ b/enos/modules/aws_rdp_member_server/main.tf
@@ -61,14 +61,15 @@ resource "aws_instance" "member_server" {
 
   user_data = <<EOF
                 <powershell>
+                  %{if var.server_version != "2016"~}
                   # set variables for retry loops
                   $timeout = 300
                   $interval = 30
 
                   # Set up SSH so we can remotely manage the instance
                   ## Install OpenSSH Server and Client
-                  # Loop to make sure that SSH installs correctly                       
-                  $elapsed = 0          
+                  # Loop to make sure that SSH installs correctly
+                  $elapsed = 0
                   do {
                     try {
                       Add-WindowsCapability -Online -Name OpenSSH.Server~~~~0.0.1.0
@@ -129,6 +130,7 @@ resource "aws_instance" "member_server" {
 
                   ## Open the firewall for SSH connections
                   New-NetFirewallRule -Name sshd -DisplayName 'OpenSSH Server (sshd)' -Enabled True -Direction Inbound -Protocol TCP -Action Allow -LocalPort 22
+                  %{endif~}
 
                   # Adds member server to the domain
                   [int]$intix = Get-NetAdapter | % { Process { If ( $_.Status -eq "up" ) { $_.ifIndex } }}
@@ -160,7 +162,7 @@ ${var.domain_admin_password}
                       Write-Host "Resovling domain after 5 minutes. Exiting."
                       exit 1
                     }
-                  } while ($true) 
+                  } while ($true)
 
                   #logging to troubleshoot domain issues
                   Resolve-DnsName -Name "${var.active_directory_domain}" -Server "${var.domain_controller_ip}" -ErrorAction SilentlyContinue
@@ -222,6 +224,7 @@ resource "time_sleep" "wait_2_minutes" {
 # BatchMode=Yes to prevent SSH from prompting for a password to ensure that we
 # can just SSH using the private key
 resource "enos_local_exec" "wait_for_ssh" {
+  count      = var.server_version != "2016" ? 1 : 0
   depends_on = [time_sleep.wait_2_minutes]
   inline     = ["timeout 600s bash -c 'until ssh -i ${local.private_key} -o BatchMode=Yes -o IdentitiesOnly=yes -o UserKnownHostsFile=/dev/null -o StrictHostKeyChecking=no Administrator@${aws_instance.member_server.public_ip} \"echo ready\"; do sleep 10; done'"]
 }
@@ -229,6 +232,7 @@ resource "enos_local_exec" "wait_for_ssh" {
 # Retrieve the domain hostname of the member server, which will be used in
 # Kerberos
 resource "enos_local_exec" "get_hostname" {
+  count = var.server_version != "2016" ? 1 : 0
   depends_on = [
     enos_local_exec.wait_for_ssh,
   ]
diff --git a/enos/modules/aws_rdp_member_server/outputs.tf b/enos/modules/aws_rdp_member_server/outputs.tf
index b09e4ee836..50e1247d03 100644
--- a/enos/modules/aws_rdp_member_server/outputs.tf
+++ b/enos/modules/aws_rdp_member_server/outputs.tf
@@ -29,6 +29,6 @@ output "password" {
 }
 
 output "domain_hostname" {
-  description = "The hostname of the domain controller"
-  value       = trimspace(enos_local_exec.get_hostname.stdout)
+  description = "The hostname of the member server"
+  value       = var.server_version != "2016" ? trimspace(enos_local_exec.get_hostname[0].stdout) : ""
 }
diff --git a/enos/modules/aws_rdp_member_server_with_worker/main.tf b/enos/modules/aws_rdp_member_server_with_worker/main.tf
index 21f5ad3c35..a1c87f1d39 100644
--- a/enos/modules/aws_rdp_member_server_with_worker/main.tf
+++ b/enos/modules/aws_rdp_member_server_with_worker/main.tf
@@ -93,8 +93,8 @@ resource "aws_instance" "worker" {
 
                   # Set up SSH so we can remotely manage the instance
                   ## Install OpenSSH Server and Client
-                  # Loop to make sure that SSH installs correctly                       
-                  $elapsed = 0          
+                  # Loop to make sure that SSH installs correctly
+                  $elapsed = 0
                   do {
                     try {
                       Add-WindowsCapability -Online -Name OpenSSH.Server~~~~0.0.1.0
@@ -158,14 +158,14 @@ resource "aws_instance" "worker" {
                   New-NetFirewallRule -Name boundary_in -DisplayName 'Boundary inbound' -Enabled True -Direction Inbound -Protocol TCP -Action Allow -LocalPort 9202
                   New-NetFirewallRule -Name boundary_out -DisplayName 'Boundary outbound' -Enabled True -Direction Outbound -Protocol TCP -Action Allow -LocalPort 9202
 
-                  ## Add computer to the domain
+                  # Add computer to the domain
                   [int]$intix = Get-NetAdapter | % { Process { If ( $_.Status -eq "up" ) { $_.ifIndex } }}
                   Set-DNSClientServerAddress -interfaceIndex $intix -ServerAddresses ("${var.domain_controller_ip}","127.0.0.1")
                   $here_string_password = @'
 ${var.domain_admin_password}
 '@
                   $password = ConvertTo-SecureString $here_string_password -AsPlainText -Force
-                  $username = "${local.domain_sld}\Administrator" 
+                  $username = "${local.domain_sld}\Administrator"
                   $credential = New-Object System.Management.Automation.PSCredential($username,$password)
 
                   # check that domain can be reached
@@ -184,7 +184,7 @@ ${var.domain_admin_password}
                       Write-Host "Resolving domain after 5 minutes. Exiting."
                       exit 1
                     }
-                  } while ($true) 
+                  } while ($true)
 
                   #logging to troubleshoot domain issues
                   Resolve-DnsName -Name "${var.active_directory_domain}" -Server "${var.domain_controller_ip}" -ErrorAction SilentlyContinue
diff --git a/enos/modules/aws_rdp_member_server_with_worker/scripts/setup.ps1 b/enos/modules/aws_rdp_member_server_with_worker/scripts/setup.ps1
index 47f734af95..2e36a12187 100644
--- a/enos/modules/aws_rdp_member_server_with_worker/scripts/setup.ps1
+++ b/enos/modules/aws_rdp_member_server_with_worker/scripts/setup.ps1
@@ -26,4 +26,4 @@ $command = "boundary server -config `"$configPath`" *> $jobLog"
 Register-ScheduledJob boundary -ScriptBlock ([ScriptBlock]::Create($command)) -Trigger $trigger
 
 # Restart the computer to apply changes
-shutdown -r -t 10
\ No newline at end of file
+shutdown -r -t 10
diff --git a/enos/modules/aws_vault/outputs.tf b/enos/modules/aws_vault/outputs.tf
index 1947ab1073..525c811ebc 100644
--- a/enos/modules/aws_vault/outputs.tf
+++ b/enos/modules/aws_vault/outputs.tf
@@ -11,6 +11,11 @@ output "instance_public_ips" {
   value       = var.ip_version == "4" ? [for instance in aws_instance.vault_instance : instance.public_ip] : flatten([for instance in aws_instance.vault_instance : instance.ipv6_addresses])
 }
 
+output "instance_public_ips_ipv4" {
+  description = "Public IPv4 addresses of Vault instances"
+  value       = [for instance in aws_instance.vault_instance : instance.public_ip if instance.public_ip != null]
+}
+
 output "instance_private_ips" {
   description = "Private IPs of Vault instances"
   value       = [for instance in aws_instance.vault_instance : instance.private_ip]
diff --git a/enos/modules/aws_vpc_ipv6/main.tf b/enos/modules/aws_vpc_ipv6/main.tf
index 1ba48517eb..f34496f3f3 100644
--- a/enos/modules/aws_vpc_ipv6/main.tf
+++ b/enos/modules/aws_vpc_ipv6/main.tf
@@ -71,6 +71,8 @@ variable "ip_version" {
   }
 }
 
+data "aws_caller_identity" "current" {}
+
 data "enos_environment" "localhost" {}
 
 check "ipv6_connection" {
@@ -174,7 +176,7 @@ resource "aws_vpc" "vpc" {
   tags = merge(
     local.common_tags,
     {
-      "Name" = var.name
+      "Name" = "${var.name}-${split(":", data.aws_caller_identity.current.user_id)[1]}"
     },
   )
 }