PowerShell remoting (WinRM) over HTTPS using a AD CS PKI (CA) signed client Certificate

This is a guide to show you how to enroll your servers/desktops to allow powershell remoting (WINRM) over HTTPS


  • You have a working Root CA on the ADDS environment – Guide
  • CRL and AIA is configured properly – Guide
  • Root CA cert is pushed out to all Servers/Desktops – This happens by default


  1. Setup CA Certificate template
  2. Deploy Auto-enrolled Certificates via Group Policy
  3. Powershell logon script to set the WinRM listener
  4. Deploy the script as a logon script via Group Policy
  5. Testing
1 – Setup CA Certificate template to allow Client Servers/Desktops to checkout the certificate from the CA

Connect to the The Certification Authority Microsoft Management Console (MMC)

Navigate to Certificate Templates > Manage

On the “Certificate templates Console” window > Select Web Server > Duplicate Template

Under the new Template window Set the following attributes

General – Pick a Name and Validity Period – This is up to you

Compatibility – Set the compatibility attributes (You can leave this on the default values, It up to you)

Subject Name – Set ‘Subject Name’ attributes (Important)

Security – Add “Domain Computers” Security Group and Set the following permissions

  • Read – Allow
  • Enroll – Allow
  • Autoenroll – Allow

Click “OK” to save and close out of “Certificate template console”

Issue to the new template

Go back to the “The Certification Authority Microsoft Management Console” (MMC)

Under templates (Right click the empty space) > Select New > Certificate template to Issue

Under the Enable Certificate template window > Select the Template you just created

Allow few minutes for ADDS to replicate and pick up the changes with in the forest

2 – Deploy Auto-enrolled Certificates via Group Policy

Create a new GPO

Windows Settings > Security Settings > Public Key Policies/Certificate Services Client – Auto-Enrollment Settings

Link the GPO to the relevant OU with in your ADDS environment

Note – You can push out the root CA cert as a trusted root certificate with this same policy if you want to force computers to pick up the CA cert,


If you need to test it gpupdate/force or reboot your test machine, The Server VM/PC will pickup a certificate from ADCS PKI

3 – Powershell logon script to set the WINRM listener

Dry run

  • Setup the log file
  • Check for the Certificate matching the machines FQDN Auto-enrolled from AD CS
  • If exist
    • Set up the HTTPS WInRM listener and bind the certificate
    • Write log
  • else
    • Write log
#Malinda Rathnayake- 2020
$Date = Get-Date -Format "dd_MM_yy"
$SessionRunTime = Get-Date -Format "dd_yyyy_HH-mm"
#Setup Logs folder and log File
$ScriptVersion = '1.0'
$locallogPath = "C:\_Scripts\_Logs\WINRM_HTTPS_ListenerBinding"
$logging_Folder = (New-Item -Path $locallogPath -ItemType Directory -Name $Date -Force)
$ScriptSessionlogFile = New-Item $logging_Folder\ScriptSessionLog_$SessionRunTime.txt -Force
$ScriptSessionlogFilePath = $ScriptSessionlogFile.VersionInfo.FileName
#Check for the the auto-enrolled SSL Cert
$RootCA = "Company-Root-CA" #change This
$hostname = ([System.Net.Dns]::GetHostByName(($env:computerName))).Hostname
$certinfo = (Get-ChildItem -Path Cert:\LocalMachine\My\ |? {($_.Subject -Like "CN=$hostname") -and ($_.Issuer -Like "CN=$RootCA*")})
$certThumbprint = $certinfo.Thumbprint
#Remove the existing WInRM Listener if there is any
Get-ChildItem WSMan:\Localhost\Listener | Where -Property Keys -eq "Transport=HTTPS" | Remove-Item -Recurse -Force
#If the client certificate exists Setup the WinRM HTTPS listener with the cert else Write log
if ($certThumbprint){
New-Item -Path WSMan:\Localhost\Listener -Transport HTTPS -Address * -CertificateThumbprint $certThumbprint -HostName $hostname -Force
netsh advfirewall firewall add rule name="Windows Remote Management (HTTPS-In)" dir=in action=allow protocol=TCP localport=$port
Add-Content -Path $ScriptSessionlogFilePath -Value "Certbinding with the HTTPS WinRM HTTPS Listener Completed"
Add-Content -Path $ScriptSessionlogFilePath -Value "$certinfo.Subject"}
Add-Content -Path $ScriptSessionlogFilePath -Value "No Cert matching the Server FQDN found, Please run gpupdate/force or reboot the system"

Script is commented with Explaining each section (should have done functions but i was pressed for time, never got around to do it, if you do fix it up and improve this please let me know in the comments :D)

5 – Deploy the script as a logon script via Group Policy

Setup a GPO and set this script as a logon Powershell script

Im using a user policy with GPO Loop-back processing set to Merge applied to the server OU


To confirm WinRM is listening on HTTPS, type the following commands:

winrm enumerate winrm/config/listener
Winrm get http://schemas.microsoft.com/wbem/wsman/1/config

Sources that helped me




Vagrant Ansible LAB Guide – Bridged network

Here’s a is a quick guide to get you started with a “Ansible core lab” using Vagrant.

Alright lets get started

TLDR Version

  • Install Vagrant
  • Install Virtual-box
  • Create project folder and CD in to it
Vagrant init
  • Vagrantfile – link
  • Vagrant Provisioning Shell Script to Deploy Ansible – link
  • Install the vagrant-vbguest plugin to deploy missing
vagrant plugin install vagrant-vbguest
  • Bring up the Vagrant environment
Vagrant up

Install Vagrant and Virtual box

For this demo we are using windows 10 1909 but you can use the same guide for MAC OSX


Download Vagrant and virtual box and install it the good ol way –




Install the vagrant-vbguest plugin (We need this with newer versions of Ubuntu)

vagrant plugin install vagrant-vbguest

Or Using chocolatey

choco install vagrant
choco install virtualbox
choco install vagrant-manager

Install the vagrant-vbguest plugin (We need this with newer versions of Ubuntu)

vagrant plugin install vagrant-vbguest

MAC OSX – using Brewcask

Install virtual box

$ brew cask install virtualbox

Now install Vagrant either from the website or use homebrew for installing it.

$ brew cask install vagrant

Vagrant-Manager is a nice way to manage all your virtual machines in one place directly from the menu bar.

$ brew cask install vagrant-manager

Install the vagrant-vbguest plugin (We need this with newer versions of Ubuntu)

vagrant plugin install vagrant-vbguest

Setup the Vagrant Environment

Open Powershell

to get started lets check our environment

vagrant version

Create a project directory and Initialize the environment

for the project directory im using D:\vagrant

Open powershell and run

mkdir D:\vagrant
cd D:\vagrant

Initialize the environment under the project folder

vagrant init

this will create Two Items

.vagrant – Hidden folder holding Base Machines and meta data

Vagrantfile – Vagrant config file

Lets Create the Vagrantfile to deploy the VMs


The syntax of Vagrantfiles is Ruby this gives us a lot of flexibility to program in logic when building your files

Im using Atom to edit the vagrantfile

Vagrant.configure("2") do |config|
     config.vm.define "controller" do |controller|
                  controller.vm.box = "ubuntu/trusty64"
                  controller.vm.hostname = "LAB-Controller"
                  controller.vm.network "public_network", bridge: "Intel(R) I211 Gigabit Network Connection", ip: ""
                    controller.vm.provider "virtualbox" do |vb|
                                 vb.memory = "2048"
                  controller.vm.provision :shell, path: 'Ansible_LAB_setup.sh'
   (1..3).each do |i|
         config.vm.define "vls-node#{i}" do |node|
                       node.vm.box = "ubuntu/trusty64"
                       node.vm.hostname = "vls-node#{i}"
                       node.vm.network "public_network", bridge: "Intel(R) I211 Gigabit Network Connection" ip: "{i}"
                      node.vm.provider "virtualbox" do |vb|
                                                  vb.memory = "1024"

You can grab the code from my Repo


Let’s talk a little bit about this code and unpack this

Vagrant API version

Vagrant uses API versions for its configuration file, this is how it can stay backward compatible. So in every Vagrantfile we need to specify which version to use. The current one is version 2 which works with Vagrant 1.1 and up.

Provisioning the Ansible VM

This will

  • Provision the controller Ubuntu VM
  • Create a bridged network adapter
  • Set the host-name – LAB-Controller
  • Set the static IP –
  • Run the Shell script that installs Ansible using apt-get install (We will get to this below)

Lets start digging in…

Specifying the Controller VM Name, base box and hostname

Vagrant uses a base image to clone a virtual machine quickly. These base images are known as “boxes” in Vagrant, and specifying the box to use for your Vagrant environment is always the first step after creating a new Vagrantfile.

You can find different base boxes from app.vagrantup.com

Or you can create custom base boxes for pretty much anything including “CiscoVIRL(CML)” images – keep an eye out for the next article on this

Network configurations

controller.vm.network "public_network", bridge: "Intel(R) I211 Gigabit Network Connection", ip: "your IP"

in this case, we are asking it to create a bridged adapter using the Intel(R) I211 NIC and set the IP address you defined on under IP attribute

You can the relavant interface name using


You can also create a host-only private network

controller.vm.network :private_network, ip: ""

for more info checkout the network section in the KB


Define the provider and VM resources

We declaring virtualbox(we installed this earlier) as the provider and setting VM memory to 2048

You can get more granular with this, refer to the below KB


Define the shell script to customize the VM config and install the Ansible Package

Now this is where we define the provisioning shell script

this script installs Ansible and set the host file entries to make your life easier

In case you are wondering VLS stands for V=virtual,L – linux S – server.

I use this naming scheme for my VMs. Feel free to use anything you want; make sure it matches what you defined on the Vagrantfile under node.vm.hostname

sudo apt-get update
sudo apt-get install software-propetise-common -y
sudo apt-add-repository ppa:ansible/ansible
sudo apt-get update
sudo apt-get install ansible -y
echo " LAB-controller vls-node1 vls-node2 vls-node3" >> /etc/hosts

create this file and save it as Ansible_LAB_setup.sh in the Project folder

in this case I’m going to save it under D:\vagrant

You can also do this inline with a script block instead of using a separate file


Provisioning the Member servers for the lab

We covered most of the code used above, the only difference here is we are using each method to create 3 VMs with the same template (I’m lazy and it’s more convenient)

This will create three Ubuntu VMs with the following Host-names and IP addresses, you should update these values to match you LAN, or use a private Adapter

vls-node1 –

vls-node2 –

vls-node1 –

So now that we are done with explaining the code, let’s run this

Building the Lab environment using Vagrant

Issue the following command to check your syntax

Vagrant status

Issue the following command to bring up the environment

Vagrant up

If you get this message Reboot in to UEFI and make sure virtualization is enabled

Intel – VT-D

AMD Ryzen – SVM

If everything is kumbaya you will see vagrant firing up the deployment

It will provision 4 VMs as we specified

Notice since we have the “vagrant-vbguest” plugin installed, it will reinstall the relevant guest tools along with the dependencies for the OS

==> vls-node3: Machine booted and ready!
[vls-node3] No Virtualbox Guest Additions installation found.
rmmod: ERROR: Module vboxsf is not currently loaded
rmmod: ERROR: Module vboxguest is not currently loaded
Reading package lists...
Building dependency tree...
Reading state information...
Package 'virtualbox-guest-x11' is not installed, so not removed
The following packages will be REMOVED:
0 upgraded, 0 newly installed, 1 to remove and 0 not upgraded.
After this operation, 5799 kB disk space will be freed.
(Reading database ... 61617 files and directories currently installed.)
Removing virtualbox-guest-utils (6.0.14-dfsg-1) ...
Processing triggers for man-db (2.8.7-3) ...
(Reading database ... 61604 files and directories currently installed.)
Purging configuration files for virtualbox-guest-utils (6.0.14-dfsg-1) ...
Processing triggers for systemd (242-7ubuntu3.7) ...
Reading package lists...
Building dependency tree...
Reading state information...
linux-headers-5.3.0-51-generic is already the newest version (5.3.0-51.44).
linux-headers-5.3.0-51-generic set to manually installed.

Check the status

Vagrant status


Connecting via SSH to your VMs

vagrant ssh controller

“Controller” is the VMname we defined before not the hostname, You can find this by running Vagrant status on posh or your terminal

We are going to connect to our controller and check everything

Little bit more information on the networking side

Vagrant Adds two interfaces, for each VM

NIC 1 – Nat’d in to the host (control plane for Vagrant to manage the VMs)

NIC 2 – Bridged adapter we provisioned in the script with the IP Address

Default route is set via the Private(NAT’d) interface (you cant change it)

Netplan configs

Vagrant creates a custom netplan yaml for interface configs

Destroy/Tear-down the environment

vagrant destroy -f


I hope this helped someone. when I started with Vagrant a few years back it took me a few tries to figure out the system and the logic behind it, this will give you a basic understanding on how things are plugged together.

let me know in the comments if you see any issues or mistakes.

Until Next time…..

Azure AD Sync Connect No-Start-Connection status


Received the following error from the Azure AD stating that Password Synchronization was not working on the tenant.

When i manually initiate a delta sync, i see the following logs

"The Specified Domain either does not exist or could not be contacted"

(click to enlarge)

Checked the following

  • Restarted ADsync Services
  • Resolve the ADDS Domain FQDN and DNS – Working
  • Test required ports for AD-sync using portqry – issues with the Primary ADDS server defined on the DNS values

Root Cause

Turns out the Domain controller Defined as the primary DNS value was pointing was going thorough updates, its responding on the DNS but doesn’t return any data (Brown-out state)


when checking DNS since the DNS server is connecting, Windows doesn’t check the secondary and tertiary servers defined under DNS servers.

This might happen if you are using a ADDS server via a S2S tunnel/MPLS when the latency goes high


Check make sure your ADDS-DNS servers defined on AD-SYNC server are alive and responding

in my case i just updated the “Primary” DNS value with the umbrella Appliance IP (this act as a proxy and handle the fail-over)

Hybrid Exchange mailbox On-boarding : Target user already has a primary mailbox – Fix

During an Office 365 migration on a Hybrid environment with AAD Connectran into the following scenario:

  • Hybrid Co-Existence Environment with AAD-Sync
  • User [email protected] has a mailbox on-premises. Jon is represented as a Mail User in the cloud with an office 365 license
  • [email protected] had a cloud-only mailbox prior to the initial AD-sync was run
  • A user account is registered as a mail-user and has a valid license attached
  • During the office 365 Remote mailbox move, we end up with the following error during validation and removing the immutable ID and remapping to on-premise account won’t fix the issue
Target user 'Sam fisher' already has a primary mailbox.
+ CategoryInfo : InvalidArgument: (tsu:MailboxOrMailUserIdParameter) [New-MoveRequest], RecipientTaskException
+ FullyQualifiedErrorId : [Server=Pl-EX001,RequestId=19e90208-e39d-42bc-bde3-ee0db6375b8a,TimeStamp=11/6/2019 4:10:43 PM] [FailureCategory=Cmdlet-RecipientTaskException] 9418C1E1,Microsoft.Exchange.Management.Migration.MailboxRep
+ PSComputerName : Pl-ex001.Paladin.org

It turns out this happens due to an unclean cloud object on MSOL, This is because Exchange online keeps pointers that indicate that there used to be a mailbox in the cloud for this user

Option 1 (nuclear option)

to fix this problem was to delete *MSOL User Object* for Sam and re-sync it from on-premises. This would delete [email protected] from the cloud – but it will delete him/her from all workloads, not only Exchange. This is problematic because Sam is already using Teams, One-drive, SharePoint.

Option 2

Clean up only the office 365 mailbox pointer information

PS C:\> Set-User [email protected] -PermanentlyClearPreviousMailboxInfo 
Are you sure you want to perform this action?
Delete all existing information about user "[email protected]"?. This operation will clear existing values from
Previous home MDB and Previous Mailbox GUID of the user. After deletion, reconnecting to the previous mailbox that
existed in the cloud will not be possible and any content it had will be unrecoverable PERMANENTLY. Do you want to
[Y] Yes [A] Yes to All [N] No [L] No to All [?] Help (default is "Y"): a

Executing this leaves you with a clean object without the duplicate-mailbox problem,

in some cases when you run this command you will get the following output 

 “Command completed successfully, but no user settings were changed.”

If this happens

Remove the license from the user temporarily and run the command to remove previous mailbox data

then you can re-add the license 


MS Exchange 2016 [ERROR] Cannot find path ‘..\Exchange_Server_V15\UnifiedMessaging\grammars’ because it does not exist.

So recently I ran into this annoying error message with Exchange 2016 CU11 Update.

Environment info-

  • Exchange 2016 upgrade from CU8 to CU11
  • Exchange binaries are installed under D:\Microsoft\Exchange_Server_V15\..
Microsoft.PowerShell.Commands.GetItemCommand.ProcessRecord()". [12/04/2018 16:41:43.0233] [1] [ERROR] Cannot find path 'D:\Microsoft\Exchange_Server_V15\UnifiedMessaging\grammars' because it does not exist. 
[12/04/2018 16:41:43.0233] [1] [ERROR-REFERENCE] Id=UnifiedMessagingComponent___99d8be02cb8d413eafc6ff15e437e13d Component=EXCHANGE14:\Current\Release\Shared\Datacenter\Setup
[12/04/2018 16:41:43.0234] [1] Setup is stopping now because of one or more critical errors. [12/04/2018 16:41:43.0234] [1] Finished executing component tasks.
[12/04/2018 16:41:43.0318] [1] Ending processing Install-UnifiedMessagingRole
[12/04/2018 16:44:51.0116] [0] CurrentResult setupbase.maincore:396: 0 [12/04/2018 16:44:51.0118] [0] End of Setup
[12/04/2018 16:44:51.0118] [0] **********************************************

Root Cause

Ran the Setup again and it failed with the same error
while going though the log files i notice that the setup looks for this file path while configuring the "Mailbox role: Unified Messaging service" (Stage 6 on the GUI installer)

$grammarPath = join-path $RoleInstallPath "UnifiedMessaging\grammars\*";

There was no folder present with the name grammars under the Path specified on the error

just to confirm, i checked another server on CU8 and the grammars folder is there.

Not sure why the folder got removed, it may have happened during the first run of the CU11 setup that failed,


My first thought was to copy the folder from an existing CU8 server. but just to avoid any issues (since exchange is sensitive to file versions)
I created an empty folder with the name "grammars" under D:\Microsoft\Exchange_Server_V15\UnifiedMessaging\

Ran the setup again and it continued the upgrade process and completed without any issues...¯\_(ツ)_/¯

[12/04/2018 18:07:50.0416] [2] Ending processing Set-ServerComponentState
[12/04/2018 18:07:50.0417] [2] Beginning processing Write-ExchangeSetupLog
[12/04/2018 18:07:50.0420] [2] Install is complete. Server state has been set to Active.
[12/04/2018 18:07:50.0421] [2] Ending processing Write-ExchangeSetupLog
[12/04/2018 18:07:50.0422] [1] Finished executing component tasks.
[12/04/2018 18:07:50.0429] [1] Ending processing Start-PostSetup
[12/04/2018 18:07:50.0524] [0] CurrentResult setupbase.maincore:396: 0
[12/04/2018 18:07:50.0525] [0] End of Setup
[12/04/2018 18:07:50.0525] [0] **********************************************

Considering cost of this software M$ really have to be better about error handling IMO, i have run in to silly issues like this way too many times since Exchange 2010.