Migrating your Microsoft PKI infrastructure to Windows Server 2016 (Part 1)

Migrating your Microsoft PKI infrastructure to Windows Server 2016 (Part 1)
Migrating your Microsoft PKI infrastructure to Windows Server 2016 (Part 2)

As part of my efforts to upgrade my POC lab to Windows Server 2016 I got around to migrating my PKI infrastructure. This consists of an offline root CA and an online issuing CA. In Part 1 of this guide I will be migrating my offline root CA to Windows Server 2016.

This guide is written as a guide to upgrade from a Windows Server 2012 R2 CA to a Windows Server 2016 CA, however very little has changed since the Windows Server 2003 days and this guide is equally valid for moving a CA from any older version of Windows server to Windows Server 2016.

I am a big advocate of the core versions of Windows Server and in this guide I will be migrating from and to Windows Server core. A CA is a perfect example of a server that does not need the overhead of the GUI and additional services that comes with the full GUI edition of Windows Server and if you don’t already use core for your CA, this is a perfect opportunity to migrate to one!


In preparation for the migration build your new Windows Server 2016 server. I recommend that you give it the same name as your current root CA server – it is possible to give it a different name however this will require changing registry keys later on in the migration process. Take this opportunity to patch it with the latest Microsoft patches!

Migration – Backing up your existing root CA server

The first step is to back up the CA using the command certutil -backup C:\RootCABackup KeepLog. Note that the KeepLog part is optional, however without it the backup will truncate the logs. I prefer to bring the whole lot across in case the logs are ever needed in the future for auditing purposes.

You will need to enter a password, remember it and make it complex. This backup contains your root CA private key, do not make it easy for an attacker to obtain.


The next thing to backup is the CA configuration, which is stored in the registry in the following location: HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\CertSvc. Back it up by typing reg export "HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\CertSvc" C:\RootCABackup\CertSvcRegBackup.reg


Additionally it is worth backing up your CAPolicy.inf file which you can do easily enough by copying it into the backup folder, by typing copy C:\Windows\CAPolicy.inf C:\RootCABackup


Finally, copy the RootCABackup folder to your new CA.

Migration – Configuring your new root CA and restoring from the backup

Log on to your new root CA server and start by installing the CA role. The easiest way to do this is with PowerShell, so type powershell into your administrative CMD prompt and enter the following command to install the CA role: Add-WindowsFeature ADCS-Cert-Authority

Now configure this new CA using the backup of the old CA. This can also be done with PowerShell using the following command:

Install-AdcsCertificationAuthority -CAType StandaloneRootCA -CertFile "C:\RootCABackup\LaptopPoc Root CA.p12" -CertFilePassword (Read-Host "Enter password" -AsSecureString)

Replace the value after -CertFile with the path and name of the .p12 file from your root CA backup. When you press enter you will be prompted for the password you used to back up your original root CA.

If this step is successful you will receive ErrorID 0 as your return code.


This restores the root CA private key, however next you need to restore the database and logs. Before you do this the CA service must be stopped. Do that by typing in net stop certsvc and pressing enter. Once it has stopped restore the database and logs using the command certutil -f -restore C:\RootCABackup. The -f forces an overwrite of the data that was configured in the barebones CA setup. Once again you must enter the password you used to backup your original root CA.


Do not start the certificate authority service just yet! Before doing that the registry settings from the previous root CA need to be restored. Do this by typing reg import "C:\RootCABackup\CertSvcRegBackup.reg"

Note: If you chose to change the name of your root CA server you will need to go through the values in this registry file and change any reference to the old server name to your new server name before importing it.

Finally copy the CAPolicy.inf file back into the Windows directory by using the command copy C:\RootCABackup\CAPolicy.inf C:\Windows

Now you can start the root CA by typing net start certsvc. The service should start with out any issues. To verify this you should log on to a management workstation and load the Certificate Authority MMC snap-in, connect to the new server and verify that your issued / revoked certificates are listed (as this is a root CA there should be very few issued certificates!)

Once you are satisfied that the new server is configured correctly and working, make sure that you delete the C:\RootCABackup folder. As previously mentioned, this contains your root CA private key, you do not want to leave that laying around!

Coming soon is Part 2, which will focus on migrating the issuing certificate authority. Thankfully the steps for this are very similar with only small differences due to it being a domain joined server.


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Error 80070057 when attempting to update Windows Server 2012 R2

Once when I was updating some servers running the version of Windows Server 2012 R2 I encountered something odd; no patches appeared in Software Center or in the Windows Update panel, even though the server was several years out of date and definitely had applicable updates!

In WindowsUpdate.log I found the following error message repeating:


The fix for this is to manually download and install KB2919355, which is the April 2014 update rollup for Windows Server 2012 R2. After this has been installed and the server has restarted, re-run your updates scan and updates will show up in Windows Update or Software Center.


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Increasing the maximum run time for Windows 10 and Windows Server 2016 cumulative updates

One of the things I have noticed since starting to deploy Windows Server 2016 is that the cumulative updates can fail to install when deployed from SCCM. It starts to run but then times out due to the maximum run time having been reached. By default this is set to 10 minutes. However due to the updates being larger and taking longer to install than updates prior to the cumulative updates era 10 minutes doesn’t seem to be long enough. The fix for this is to simply increase the maximum run time for cumulative updates for both Windows Server 2016 and Windows 10 from 10 minutes to 30 minutes.

Screen Shot 2017-06-05 at 23.12.35

Screen Shot 2017-06-05 at 23.12.47

This is a bit tedious as you’ll have to do it every month for both Windows Server 2016 and every version of Windows 10 you have in your environment. Hopefully Microsoft soon catches on to this and changes the default run time to 30 minutes so that this ceases to be an issue. There is already a Configuration Manager UserVoice entry for this idea, so if you’re reading this, pop over and vote to increase its visibility!


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ISATAP failing with error 0x490

ISATAP can be very useful if you need to manage out from a machine with an IPv4 address to a machine with an IPv6 address. This is commonly used where DirectAccess has been deployed as all DA clients will be using IPv6. Being able to RDP to them or use the SCCM Remote Control feature from a machine inside your network is very helpful for the IT support staff – it’s as if the user was just working from their desk like usual!

One time I was configuring an ISATAP interface on a server and I got the follow error in the event log:

Unable to update the IP address on ISATAP.yourdomain.com. Update type: 1. Error Code: 0x490

I scratched my head over this for quite a while – setting up an ISATAP interface should be easy! After a while I remembered that there was a history of disabling the IPv6 components on servers via GPO. It turns out that even though the GPO had been removed, the setting to disable IPv6 had been tattooed on the servers it had once been applied to.

To check this I had a look in the following location in the registry:


The value was set to 0xFFFFFFFF (it may instead be set to 0xFF). This disables enough of the IPv6 components to prevent an ISATAP interface from being able to be created.

Simply delete the DisabledComponents key and restart the server. So long as everything else is set up correctly you will have your ISATAP interface when you next log in.
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Automatically enable BitLocker and set a PIN during an SCCM Task Sequence

Getting your operating system deployment one step closer to being zero touch is always a good goal, so with that in mind here is how to automatically enable BitLocker during OSD using a PIN that you define in a variable at the beginning of the Task Sequence.

The first thing to do is add the OSDBitlockerPIN variable to the collection you advertise your OSD Task Sequences too. This is very likely the All Unknown Computers collection. Right click on it and select Properties. Navigate to the Collection Variable tab and click New. The name is OSDBitlockerPIN and you should untick “Do not display this value in the Configuration Manager console”.


Next up open your Task Sequence and add the Enable BitLocker step. This can be placed anywhere after the Setup Windows and ConfigMgr step.1 Make sure Current operating system drive is selected and then select TPM and PIN. You can then enter anything into this field as it will be overwritten by what you enter into the OSDBitlockerPIN variable when you start the Task Sequence.


Finally, go ahead boot your client into the WinPE environment. Select your Task Sequence and click next and you will be presented with the Edit Task Sequence Variables step. You may already use the OSDComputerName variable in which case you will already be familiar with this! Double click on OSDBitlockerPIN and enter the PIN you wish to use for this machine.


Click Next and the Task Sequence will run and complete. BitLocker will be enabled and the PIN will be set. Now you don’t have to configure BitLocker after the operating system has been deployed!

1I would add the Enable BitLocker step at the very end of your Task Sequence, otherwise you will have to enter the PIN each time the machine reboots after applications or updates are installed. You could suspend BitLocker before each reboot, but why go to the extra effort.


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Windows 7 client failing to connect to RD Web resources

Here is an issue you might encounter on Windows 7 if you are trying to connect to Remote Desktop Web Access (RD Web) or use Remote Desktop Connection with a gateway that is hosted by a Windows Server 2012 (R2) server.

You browse to the RD Web URL, log in and click on the application you want to launch. It appears to start connecting, but then prompts you for credentials. You put them in, click OK and wait a while… it appears to be connecting… and then the credentials box appears again. This continues forever in a loop.

Similarly if you try to RDP to a machine inside your corporate network with a RD Gateway server set, you enter the computer name and your username and click Connect. You are prompted for a password, enter it and click OK, but a few moments later the credentials box appears again.

This is likely being caused by the version of the Remote Desktop Protocol you are running being version 7.0 (Windows 7 RTM) or 7.1 (SP1 onwards). To connect to RD Web or use a gateway being hosted by a Windows Server 2012 (R2) server you must be running Remote Desktop Protocol 8.0 or 8.1. This is achieved by installing the following three updates (in order):


To check what version of the Remote Desktop Protocol you are running open up an Remote Desktop Connection window and click on the title bar icon, select About and the version is presented in the last line (mine says “Remote Desktop Protocol 8.1 supported.”)


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Scan failed with error 0x80244021 with WinHTTP proxy configured

While trying to update one particular server using SCCM 2012 R2 I discovered that it was not updating, with the following error was appearing in WindowsUpdate.log and UpdatesHandler.log:

Scan failed with error = 0x80244021

In my case this issue was occurring because a proxy server was configured but no exception was in place for the WSUS / SCCM server. This meant that the server was trying to access the WSUS server through the proxy! To see what my proxy settings were I opened an elevated CMD prompt and entered the following command:

netsh winhttp show proxy

The following information was returned:

Proxy Server(s): ProxyServer.local
Bypass List :

As you can see, the bypass list is empty. In order to create an exception for the WSUS server, enter the following command:

netsh winhttp set proxy ProxyServer.local "https://WSUSServer.local" 1, 2

This sets the proxy and sets the WSUS server as an exception. Re-running netsh winhttp show proxy will now show you the following output:

Proxy Server(s): ProxyServer.local
Bypass List : https://WSUSServer.local

As you can see the WSUS server is now part of the bypass list, meaning that attempts to access this website will not go through the proxy.

Restart the WindowsUpdate service and re-run the Windows Update scan. You should no longer see scan error 0x80244021.

1Whether you use HTTP or HTTPS for your WSUS server depends on your WSUS or SCCM configuration.

2If you need to add multiple exceptions enter the first one, followed by a comma, followed by the next one and so on.


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