Category Archives: Security

Security Concerns with Windows 365–aka Cloud PC

Cloud PC (sold as the Windows 365 Product SKU) is the latest Virtual Desktop service hosted by Microsoft in Azure. This post (Part 1) documents some of the security concerns that Infosec Twitter has identified. Part 2 will explore ways to harden CloudPC/Windows 365.

Cloud PC (Announced 7/14/2021 and Generally Available 8/2/2021)

Azure Virtual Desktop (Announced 6/7/2021) 

Windows Virtual Desktop (9/30/2019)

Azure RemoteApp (Retired on 8/31/2017)

Rand Morimoto wrote a nice write-up on Cloud PC (here), and the differences between it and Azure Virtual Desktop (here). Indeed, many have written articles on it, but the reason for this blog post is to examine the security and respond to some of the harsh criticism on Twitter (the InfoSec community on Twitter is probably the best ‘accountability’ buffer to keep Microsoft in check).

Most of what I have written about securing AVD/WVD (Part 1) and (Part 2) applies equally to Cloud PC. But what I love most about the business edition of Cloud PC is it eliminated all the overhead associated with spinning up the AVD/WVD environment (see Part 1 above to appreciate that effort). The Enterprise Edition requires some additional work but not as much as AVD/WVD, as explained in this Mechanics video here. There are already troubleshooting articles on the Hybrid Azure AD requirements here.

When I created my first Cloud PC, the provisioning process failed. I found out that there were issues with provisioning as described in the forums here. Turns out there were multiple issues and so I have published a separate blog post ‘Troubleshooting Windows 365 business’ here].

As an end user, you access your Cloud PC from:

Also, it’s worth noting that on August 15th 2021, Microsoft is making Cloud PC available for end users to purchase on their own credit cards. IT Departments can disable this with PowerShell.

Install-module MSCommerce


W365 Enterprise – update-MSCommerceProductPolicy -PolicyId AllowSelfServicePurchase -ProductId CFQ7TTC0HHS9 -Enabled $false

W365 Business/w Hybrid Benefits – update-MSCommerceProductPolicy -PolicyId AllowSelfServicePurchase -ProductId CFQ7TTC0J203 -Enabled $false

W365 Business – update-MSCommerceProductPolicy -PolicyId AllowSelfServicePurchase -ProductId CFQ7TTC0HX99 -Enabled $false”

Learn More: Use AllowSelfServicePurchase for the MSCommerce PowerShell module | Microsoft Docs

So why has Twitter been so unforgiving?

1. InfoSec Twitter does not like the default configuration of Local Administrator rights being given to the Cloud PC user. They claim this is not “secure by default.” It’s hard to argue with them on this point.
(1) Benjamin Delpy on Twitter: “Windows 365 is expensive and without basic security Did #mimikatz dumped my Azure *cleartext* password here? Or my Primary Refresh Token? It’s funny how you don’t apply best practices you recommend to the customer to avoid securing by default >” / Twitter
It does appear Microsoft is exploring solving this according to this thread here:
Windows 365 Business Cloud PC Local Admin – Microsoft Tech Community

2. Mimikatz has been updated to dump Windows 365 credentials

(1) Benjamin Delpy on Twitter: “After a little bug report from @LawrenceAbrams, I just pushed a #mimikatz fix to dump even more #Windows365 credentials privilege::debug ts::logonpasswords >” / Twitter


(1) Benjamin Delpy on Twitter: “Would you like to try to dump your #Windows365 Azure passwords in the Web Interface too? A new #mimikatz release is here to test! (Remote Desktop client still work, of course!) > cc: @awakecoding @RyMangan” / Twitter

3. Lack of SecureBoot, UEFI, Credential Guard, etc
(1) Benjamin Delpy on Twitter: “Figure 1. VM with hardware enforced security, vTPM, SecureBoot, UEFI, Credential Guard, etc. Figure 2. #Windows365 without basic hardware security, no security feature, BIOS Guess the one running on an old ESXi in basement vs the new 365 revolution from Microsoft in #Azure ?” / Twitter

Disable Exchange Online Remote PowerShell for users as a scheduled task

This PowerShell script can run unattended as a scheduled task and will enumerate the global administrators, then remove remote PowerShell access for any user who is not a global administrator.

#See Prerequisites section below to create these two certificate connection scripts below

Invoke-Expression -Command C:\scripts\connect-certificate.ps1

Invoke-Expression -Command C:\scripts\connect-azureadcertificate.ps1

$GlobalAdmins = Get-AzureADDirectoryRoleMember -ObjectId $(Get-AzureADDirectoryRole -filter “displayname eq ‘Global Administrator'”).ObjectID

$AllUsers = get-user -resultsize unlimited

$UserswithPowerShell = $AllUsers | where {$_.RemotePowerShellEnabled -eq $true}

$UsersWhoAreNotGlobalAdmins = $UserswithPowerShell | where {$_.userprincipalname -notin $GlobalAdmins.userprincipalname}

$counter = ($UsersWhoAreNotGlobalAdmins).count
$current = 1

if ($UsersWhoAreNotGlobalAdmins) {
write-host “Users who currently have remote powershell access” ($UserswithPowerShell).count
foreach ($user in $UsersWhoAreNotGlobalAdmins) {
write-host “Removing PowerShell access from user ” $current ” of ” $counter “(” $user.userprincipalname “)”
set-user -identity $user.userprincipalname -RemotePowerShellEnabled $false

#Optional, the next statement can also apply a authentication policy to block basic auth

#Set-User -identity $user.userprincipalname -AuthenticationPolicy “Block Basic Auth”
$current = $current + 1

write-host “there are no non-global admin users with PowerShell access”

Download the script (here).

Prerequisites: Create two Azure AD Applications (1) Exchange and (2) Azure AD

TIP: When creating the Scheduled Task,  the account must have the Logon as a service right assigned. Then the ‘action’ to start a program points to c:\windows\system32\windowspowershell\v1.0\powershell.exe
then the arguments are: -File “c:\scripts\scriptname.ps1”

Is your Exchange Hybrid Server internet-facing? You have likely already been hacked

– This is twice as big as the SolarWinds breach.

– Patching is not enough! If your Exchange Server was open to the internet via TCP 80 or 443 between February 26 and March 3rd (or later) assume it was compromised.

At least 30,000 organizations have had a backdoor installed on their Microsoft Exchange Server (on-premises).

We know it is at least this many because researchers have built an NMAP script to scan the internet for infected hosts.

There is nothing to indicate that Exchange Online has been impacted, but organizations in O365 could still have been hacked because most of those customers still have an internet-facing Exchange Hybrid server.

How to hunt for the existence of a backdoor known as a web shell.
(A web shell is an internet accessible web page that the hacker places on the Exchange Server that gives the attackers administrative access to the Exchange Server)

Indicators of Compromise 

<random_name>.aspx (often 8 characters)

In these directories:

o c:\inetpub\wwwroot\aspnet_client\

o c:\inetpub\wwwroot\aspnet_client\system_web\

o C:\Exchange\FrontEnd\HttpProxy\owa\auth\

o %PROGRAMFILES%\Microsoft\Exchange Server\V15\FrontEnd\HttpProxy\owa\auth\

– Signs of large amounts of SMB network traffic from the Exchange Server to internal network

– Scheduled Task on Exchange Server named Winnet

– Check for suspicious .zip, .rar, and .7z files in C:\ProgramData\, which may indicate possible data exfiltration.

– Monitor c:\root and c:\windows\temp for LSASS dumps (attackers used procdump64.exe) or rundll32 C:\windows\system32\comsvcs.dll MiniDump lsass.dmp

In some cases, additional dynamic link libraries (DLLs) and compiled aspx files are created shortly after the  webshells are first interacted with via POST requests in the following locations:

  • C:\Windows\Microsoft.NET\Framework64\<version>\Temporary ASP.NET Files\root\
  • C:\Windows\Microsoft.NET\Framework64\<version>\Temporary ASP.NET Files\owa\

Administrator is removed from the “Exchange Organization administrators” group (credit rapid7)

– Scan Exchange Logs for IOCs (manually here) or with the Microsoft script (here)

– You can also use this NMAP script to see if your servers are vulnerable after patching them.

In the attacks observed, the threat actor used these vulnerabilities to access on-premises Exchange servers which enabled access to email accounts and allowed installation of additional malware to facilitate long-term access to victim environments.

On March 6th, a security researcher created a honeypot with these vulnerabilities and found that it was exploited 5 times in less than 24 hours. This indicates several copy-cat threat actors are already targeting these vulnerabilities.

If you find evidence of compromise, activate your incident response procedures. You may have a legal requirement to notify within 72 hours of sensitive data was accessed in your email or network.

What versions are affected?

– Exchange 2013 Versions < 15.00.1497.012

– Exchange 2016 CU18 < 15.01.2106.013

– Exchange 2016 CU19 < 15.01.2176.009

– Exchange 2019 CU7 < 15.02.0721.013

– Exchange 2019 CU8 < 15.02.0792.010

– Microsoft issued CU 31 for Exchange Server 2010 – best to apply that, but it would be better to upgrade your hybrid server since Exchange 2010 normally does not receive security updates (this was a kind gesture on Microsoft’s part).

How do we prevent this from happening again?

– The only reason an Exchange Hybrid Server should still be internet-facing is if there are still on-premises mailboxes. Move those to the cloud and then shut off internet access to your hybrid server after moving the Autodiscover DNS record to point to

– If you have no on-premises mailboxes, you should close TCP 80/443 after moving Autodiscover to cloud

Learn more: Read the announcement, or view the Exchange blog. We also recommend the Volexity post (here) and Rapid7 post (here).

US Agencies and FireEye Were Hacked Using SolarWinds Software Backdoor

Multiple news sources are attributing the recent breaches (FireEye, the U.S. Treasury, and the U.S. Commerce Departments) to the same group: ATP29 Cozy Bear. The type of attack used is called a supply chain attack where a software vendor is targeted in order to breach the end-customer of that software. In this case, it was SolarWinds’ Orion Network Monitoring Software, which said their March and June 2020 software releases were compromised. Microsoft researchers have observed two files in October 2019 with code anomalies in the SolarWinds DLL, so it is possible that the initial access into SolarWinds may have occurred six months or longer before the malicious updates started spreading. The company estimates 18,000 of its 300,000+ customers may have installed the malicious update (this would make it the 2nd largest in history behind Citrix who had a similar attack happen to them with their install base of 400,000 customers – more on that later). SolarWinds is used by all five branches of the U.S. military, the Pentagon, State Department, Justice Department, NASA, the Executive Office of the President, the National Security Agency, the top 10 U.S. telecommunications companies, and 425 of the Fortune 500.
[Update 12/18/2020 So far Microsoft has identified 40 customers who may have been impacted, including Microsoft itself].
[Update 12/20/2020 A Chinese group called RedDrip posted on Twitter that they decoded the dynamically generated domain names that this malware used to communicate with C2, revealing the customer names that were hit. Others have used their code to post the customer lists on Pastebin (here and here).]

An emergency directive issued by the U.S. government agency Cybersecurity and Infrastructure Security Agency (CISA) calls on all federal civilian agencies to disconnect or power down SolarWinds Orion IT management tools because they are being used to facilitate an active exploit. Everyone else would be wise to follow this guidance too. CISA encourages affected organizations to read the SolarWinds and FireEye advisories for more information and FireEye’s GitHub page for detection countermeasures.

The Microsoft advisory from 12/13/2020 adds “if you suspect you are impacted you should assume your [email] communications are accessible to the actor” because the techniques observed including modifications to authentication to give persistence to email in Exchange Online, with clever techniques: “By impersonating existing applications that use permissions like Mail.Read to call the same APIs leveraged by the actor, the access is hidden amongst normal traffic.” Attackers apparently exported the private key from the ADFS token signing certificate and used that to forge SAML to gain access to cloud apps and on-premises resources. Therefore, if you use ADFS, you should consider changing the token signing certificate, or follow NSA’s recommendation to use Azure as the IDP instead of ADFS.

These supply chain attacks are not uncommon. In March of 2019 the FBI informed Citrix that they had been infiltrated for five months, as reported by Brian Krebs. In 2013, the US retailer Target was thought to be breached by a supply chain attack involving their HVAC system. In the Wipro’s data breach, hackers used ScreenConnect (ConnectWise) to gain access to their customer systems. NotPetya gained access through the accounting software M.E.Doc.

Since Microsoft’s Office 365 email may have been “an attack vector” used by the hackers, be sure to watch our best practices webinar series to secure your Office 365 environments. This is especially important if you are a software vendor for now obvious reasons, hackers want to use you to get into your customer installation base.

Always Assume Breach

Supply chain attacks highlight an important security principle: You should always assume that you have already been breached. For most organizations, it is not practical to review software update, nor would you have the original source code anyway. It’s better to just assume you have already been breached and adopt a mindset to always be ‘hunting’ for intruders. The attackers used signed binaries using Symantec certificate with thumbprint: 0fe973752022a606adf2a36e345dc0ed, meaning application control solutions that block unsigned executables would not have blocked the malicious backdoor from executing. According to this SANS video discussing the attack, the SolarWinds backdoor waits 12 to 14 days before sending its first beacon, presumably to avoid anti-malware sandbox detection or network-based behavioral learning periods.

Microsoft provides several tools that detect anomalous behavior, and provide hunting tools, including:  Azure Sentinel, Microsoft Defender for Endpoint, Microsoft Defender for Identity, and Microsoft Cloud App Security.
Note: Microsoft has already updated Microsoft Defender to detect the malicious code in the SolarWinds Orion product as “Trojan:MSIL/Solorigate.B!dha”.  My former colleague Matthew Dowst wrote a few hunting queries to detect the modifications to federation trusts and oAuth. [Update 1/4/2021]  CISA has published a tool to automate the detection (here). The issue is that the audit logs only go back so far (90 days unless Advanced Audit license was enabled).

[Update 12/23/20] For customers who had their Azure logs backing up to a Log Analytics (aka Azure Monitor) workspace then there is a new workbook that can help identify if suspicious activity in the tenant occurred.

  1. Modified application and service principal credentials/authentication methods
  2. Modified federation settings
  3. Azure AD STS Refresh token modifications by service principals and applications other than DirectorySync
  4. New permissions granted to service principals
  5. Directory role and group membership updates for service principals

Reference: Azure AD workbook to help you assess Solorigate risk – Microsoft Tech Community

[Update 12/24/2020] Just stumbled on this new guidance for Incident Responders from Microsoft here:

Advice for incident responders on recovery from systemic identity compromises – Microsoft Security

Includes some very helpful O365 forensic tools such as Hawk.

Need Help?

If you need expert assistance hardening Office 365, send us a request and we would be glad to help. Email us at Secure365 at

Does Defender scan USB drives?

No, not by default. But this isn’t as bad as it sounds! Here is Microsoft’s explanation from ~four years ago:

“Historically, antivirus products had a function to scan all files when a removable device was mounted. However, with the increase in device storage capacity, full scans of removable devices can noticeably and severely impact performance. Today, Windows Defender Antivirus performs quick scans on the contents of removable devices (such as USB drives), before the contents are copied, or executed. This approach both mitigates the risk that a malicious threat can infect the host through a removable device, while maintaining host performance. (A dormant file on a removable drive cannot infect a host). However, if needed, Windows Defender Antivirus can be configured to perform a custom scan on all files when removable devices are mounted. Below is a sample script for achieving this scenario Reference: TechNet Custom scan a USB drive (

And a more recent, albeit abbreviated explanation from November 2020:

“You can optionally run a PowerShell script to perform a custom scan of a USB drive after it is mounted, so that Microsoft Defender Antivirus starts scanning all files on a removable device once the removable device is attached. However, we recommend enabling real-time protection for improved scanning performance, especially for large storage devices. Reference: How to control USB devices and other removable media using Intune (Windows 10) – Windows security | Microsoft Docs

I tested the “scanusb.ps1” script and it failed to detect the sample malware file on a USB Drive.




Also, the CPU spiked to 13% for the duration of the scan on the large drive.


But as soon as you attempt to interact with the file then its immediately caught by the AV engine:


Also, be aware that The default behavior for scheduled scans is to not scan removable media. You can enable it with Group Policy or running this confusing double-negative PowerShell command: set-MpPreference -disableRemovabledrivescanning $false

Therefore, I agree with Microsoft with this design decision and I will be guiding my clients to stick with the defaults which protect the machine from malware while avoiding costly CPU hits. 

Defender for Endpoint (MDATP) for Windows Servers

[Update: 10/7/2021] Microsoft released to public preview a unified installer so that Windows Server 2012 R2 and 2016 now have a single installer for both AV and EDR. The prerequisite is to deploy MS KB5005292 first.
Read the announcement here:

Microsoft Defender for Endpoint (MDE) supports four versions of Windows Server: 2008 R2, 2012 R2, 2016, and 2019*

Windows Server 2016 was the first version of Windows to feature native antivirus protection “for free”. It was then called Windows Defender AV and is now called Microsoft Defender AV. This is not to be confused with what was then called Advanced Threat Protection (WDATP or MDATP), and what was recently renamed Microsoft Defender for Endpoint. Back then the ATP added Endpoint Detection and Response (EDR) on top of the AV/EPP. And it was originally available through a separate “Azure Security Center” (ASC) subscription for approximately $15/server/month. However in 2020, Microsoft began to sell EDR for servers for $4.99/server/month (I believe the minimum QTY is 50 servers, contact a MSFT CSP or License Reseller for an exact quote). Note: At the Ignite 2020 conference, Microsoft rebranded parts of Azure Security Center to “Azure Defender” (reference).

But what if you needed a antivirus for earlier versions of server operating systems such as 2012 R2 or 2008 R2? Back then your option was System Center Endpoint Protection (SCEP), or if it is hosted in Azure you can deploy the free “Microsoft Antimalware for Azure” (MAA) which is the same antimalware platform that SCEP uses. The SCEP AV client is managed  with Group Policy or SCCM. See Yong Rhee’s blog here for more details on down-level client management (I included some details from his blog in the management section below).

There are three unique deployment scenarios for protecting Windows Server Operating Systems:




2008 R2 Yes Yes (N/A)
2012 R2 Yes Yes (N/A)
2016 No Yes Natively Installed
2019 No No Natively Installed

Scenario 1) Windows Server 2008 R2 and 2012 R2.

Separate deployment of SCEP (or MAA) (to get AV and EPP), and then the Microsoft Management Agent (MMA) to get EDR from the Microsoft Defender for Endpoint management console (

System Center Endpoint Protection (SCEP) can either be  distributed using GPO, System Center Configuration Manager (SCCM), or any software distribution tool of choice. SCCM is not a requirement to use SCEP but you must have access to the Endpoint Protection client installation package, scepinstall.exe. Find this package in the Client folder of the Configuration Manager installation folder on the site server.

Microsoft Defender for Endpoint (formerly known as MDATP) provides the EDR agent (aka MMA, or Microsoft Management Agent) and you would distribute this using SCCM, Group Policy, or your software distribution tool of choice.

The MMA agent has a prerequisite hotfix which should be on your servers if you apply all recommended updates. If you have some older servers that are infrequently patched, be sure to install the prerequisite hotfix (here).

MAA for Azure virtual machines offers a lightweight management option when first deploying to servers, with no central management, so its something to consider perhaps for a DMZ.


Scenario 2) Windows Server 2016

No need to deploy SCEP because Defender AV is natively built-in.

But you must deploy MMA either through Azure Defender or Microsoft Defender for Endpoint management console ( > Settings > Onboarding.

Scenario 3) Windows Server 2019

No need to deploy SCEP because Defender AV is natively built-in.

No need to deploy MMA, because EDR is natively built-in.  Since there is no MMA to deploy, Azure Defender (aka Azure Security Center) does not automatically onboard Windows Server 2019, and therefore it is mandatory at the time of this writing to onboard using the instructions in Microsoft Defender for Endpoint management console ( > Settings > Onboarding.

Microsoft Defender AV Management Settings

In Windows 10, Windows Server 2016, and Windows Server 2019, use the Group Policy (GPO) :

Computer Configuration –> Administrative Templates –> Windows Components –> Windows Defender Antivirus

This modifies the following registry key: Hkey_Local_Machine > Software > Policies > Microsoft > Windows Defender

However, in Windows Server 2012 R2, Windows 8.1, Windows Server 2012, Windows 8, Windows Server 2008 R2 SP1, Windows 7 SP1, Windows Server 2008 SP2, Windows Vista, you use a non-existent Group Policy (GPO):

Computer Configuration –> Administrative Templates –> Windows Components –> Endpoint Protection

This modifies the following registry key: Hkey_Local_Machine > Software > Policies > Microsoft > Microsoft Antimalware

So how do you get “Endpoint Protection” to show up? For this, see the procedure here: Manage Endpoint Protection using Group Policies – Configuration Manager | Microsoft Docs

Some IT Departments do not run traditional “AV” or “EPP” on their Windows Servers. They have their reasons, but its typically based on a threat model where if a strong firewall is deployed on server to prevent inbound communications, then the theory is that threats shouldn’t wind up on the server. The issue with this is GPO and other software distribution tools – you want some layered option to block threats from getting distributed via alternate means. So I do recommend SCEP for down-level servers.


*Server 2019 is also known as Long-Term Service Channel (LTSC). While MDE also supports the Semi-Annual Channel (SAC) versions of Windows Server, it is beyond the scope of this blog article to discuss the pros and cons of SAC (instead refer to Comparison of Windows Server Servicing Channels).

Defender for Endpoint on iOS

The public preview of Defender for Endpoint on iOS can be installed by browsing to

Prerequisites: iOS 11.0 or higher, and the mobile device has Intune Company Portal App.

Lesson Learned: If you have the Azure AD Conditional Access policy enabled “Require Compliant App” then you need to exclude the Microsoft Defender app from the policy otherwise you will receive this message:


Smishing is, essentially, phishing via text messages. The word is a combination of “phishing” and “SMS,” the latter being the protocol used by most phone text messaging services.


Microsoft Defender for Endpoint creates a local VPN tunnel that redirects all outbound traffic that originates from the device to be scanned for threats, specifically websites that are malicious.


Here is an example of the block page:


Then Administrators can view these events in the Defender security portal (


You can also block specific websites or even categories of websites such as Shadow IT if you have Microsoft Cloud App Security. See Matt Soseman’s video on Youtube (here) for more information about that integration.

What happened to Defender running in a Sandbox? MP_FORCE_USE_SANDBOX

A colleague asked me today “Does Microsoft Defender run itself in a sandbox by default, or does that need to be manually enabled?”

He was referring to a breakthrough feature first announced (here) two years ago (10/26/2018)

We all know Defender can detonate files in a cloud sandbox – but we are talking about Defender running *itself* (MSMPENG.EXE) inside a sandbox.

This was a big deal at the time it was announced, because Defender was the first Antivirus product to run *itself* in a sandbox. I had read reports that 30% of all malware targeted security software since it runs with such high privileges, so this was and is a very big deal.

Running Windows Defender Antivirus in a sandbox ensures that in the unlikely event that Defender itself has vulnerabilities and becomes compromised, malicious actions are limited to the isolated environment, protecting the rest of the system from harm, since Defender runs with such high system privileges.

This feature is enabled with a machine-wide environment variable (setx /M MP_FORCE_USE_SANDBOX 1) and then restarting the machine (System requirement: Windows 10, version 1703 or later)

How can I tell if Defender is running itself in a Sandbox? Check task scheduler and if you see “CP.exe”


Sysinternals will show “App Container” 


You can also run CMD.exe followed by the SET command by itself to see if the environment variable is present:


So the question is, has Microsoft now built this into the operating system by default?

I created some fresh Win10 VM’s with Defender and did not see the CP.exe tailing process name.

So my big question is: why after two years hasn’t it been turned on by default? Is Microsoft aware of any risks or problems when this is enabled? And why is there no MEM/Intune configuration to enable this setting?

Defending against Pass-the-PRT

[Update: pass-the-PRT (CVE-2021-33779) has been patched in the July 13 2021 Windows 10 cumulative security patch (KB5004237)]

The Azure AD Primary Refresh Token (PRT) can be extracted using ROADtools, written by security researcher Dirk-jan Mollema and recently weaponized into Mimikatz by Benjamin Delpy.

With local Administrator privileges it becomes possible to extract the PRT and the required cryptographic material to sign in on any Azure AD connected resource with the account to which the PRT was issued. The PRT is valid for 14 days and can be used on any device in this time-frame. Any MFA claims that were assigned to the PRT remain valid as well.

It’s important to understand exactly how this attack works so that you can test your defenses against it. You should never assume that your defenses are adequate. Just like a backup is not good unless it is restored, your defenses are not good unless you test them frequently and thoroughly.

A PRT is only issued to native apps (like the full Outlook client) on Azure AD Registered, Azure AD Joined, or Hybrid Azure AD joined devices. A browser session on a workgroup machine will not receive a PRT. To learn more about how PRT’s are issued, see this article:

The attacker runs a few mimikatz commands:



The PRT can then be imported into Chrome as a cookie:


And this allows the attacker to sign in as the user, even if their device is not Intune compliant or Hybrid Azure AD joined.

Defending against Pass-the-PRT

There are ~15 Attack Surface Reduction Rules (ASR) in Windows 10. The following rule can be enabled in Audit or Block mode. We strongly recommend Audit mode first because Block mode may block legitimate processes that you will need to exclude before deploying this in production. On a single test machine you can run this command for audit mode:

Add-MpPreference -AttackSurfaceReductionRules_Ids 9e6c4e1f-7d60-472f-ba1a-a39ef669e4b2 -AttackSurfaceReductionRules_Actions AuditMode

And this command for block mode:

Add-MpPreference -AttackSurfaceReductionRules_Ids 9e6c4e1f-7d60-472f-ba1a-a39ef669e4b2 -AttackSurfaceReductionRules_Actions Enabled

And when this ASR rule is enabled, we can see that Mimikatz is unable to dump the PRT


Normally this should get logged as Event 1121 (Block) or 1122 (Audit) in the Event Viewer: Microsoft-Windows-Windows Defender/Operational

Or if you have Microsoft Defender ATP then in the Timeline view you can filter on ASR Events:



1. Do not grant users local administrator privileges

2. Enable Tamper Protection in Windows Defender. It is more difficult for Mimikatz to run when Defender AV is running.

3. Enable Attack Surface Reduction Rules (ASR)  to block access to LSASS.exe

What is Double Key Encryption (DKE)?

Today Microsoft announced the public preview of Double Key Encryption (DKE).

What does “Double Key” mean? It’s similar to a missile launch where two people must turn their key at the same time. In the case of encryption, it is the combination of two keys held by separate parties that encrypt or decrypt data.


Or to quote Microsoft:

“Double Key Encryption enables you to protect your highly sensitive data while keeping full control of your encryption key. It uses two keys to protect your data—one key in your control, and a second key is stored securely in Microsoft Azure. Viewing data protected with Double Key Encryption requires access to both keys. Since Microsoft can access only one of these keys, your protected data remains inaccessible to Microsoft, ensuring that you have full control over its privacy and security.”

Your Client Key is hosted outside of Microsoft (wherever you want) via a web service that you are responsible for hosting. If your web service goes down (intentionally or unintentionally) then no new data can be encrypted or decrypted.

This is similar to its predecessor, Hold-Your-Own-Key (HYOK) which I assume DKE will eventually replace at some point in the future. Except there is one big advantage: Unlike HYOK, DKE does not depend upon on-premises Active Directory Rights Management Services (AD RMS). So it is a simpler configuration.

Is DKE right for me? Most likely not. It’s intended for some super rare scenarios that very few clients have. There are serious productivity limitations to DKE that are nearly identical to HYOK, where many features inside Office 365 and other services will not function such as SharePoint Search, eDiscovery Search, Data Loss Prevention, Transport Rules, Exchange ActiveSync, Journaling, Malware scanning, Archiving Solutions and any other services that needs to read data such as 3rd party document management systems.

Therefore customers should carefully evaluate all key options before proceeding with DKE (see table below).

What if I lose my key? Your data is inaccessible, and there is no ‘back door’ key like the ‘Availability Key’ feature in BYOK that allows Microsoft to decrypt data if you lose your BYOK key.

Encryption Key Comparison



Double-Key Encryption (NEW) BYOK

Managed Key

Can Microsoft Read the Encrypted Data? No No Yes Yes
AD RMS Required? Yes No No No
100%Cloud Hosted No No Yes Yes
On-Prem or Cloud
DMZ Req?
No Yes No No
HSM Req?
Yes Yes Yes No
ActiveSync Support No No No No
Exchange On-Premises IRM No No Yes Yes
Outlook Mobile No No Yes Yes
OWA No No Yes Yes
Office Mobile


Yes (Consume Only) Yes (Consume Only) Yes Yes
Mac OSX Yes (Consume Only) Yes (Consume Only) Yes Yes
SharePoint Search No No Yes Yes
Key Strength RSA 2048-bit (Key Exchange)

AES 128 (Wrapping)

SHA 256 (Signing)

(FIPS 140-2)

RSA 2048-bit (Key Exchange)

AES 128 (Wrapping)

SHA 256 (Signing)

(FIPS 140-2)

RSA 2048-bit (Key Exchange)

AES 128 (Wrapping)

SHA 256 (Signing)

(FIPS 140-2)

RSA 2048-bit (Key Exchange)

AES 128 (Wrapping)

SHA 256 (Signing)

(FIPS 140-2)

External Collaboration No No Yes Yes
Office Client Support Office 2013 + Office Insider* Office 2013 + Office 2010 +
Auditing Yes Yes Yes Yes

Office Insider is required at the time of this writing (July 2020) but eventually it will roll out to Office versions in mainstream support.

Initially at the time of this writing, the AIP Unified Labeling Client is required to encrypt/decrypt content. It will eventually be available natively in the Office Ribbon.

Additional Resources

Blog Post:
Deployment Docs:
Github Repo:
Update [10/22/2020] Host DKE on IIS, using an on-premises server – Microsoft Tech Community