Category: Windows 11

Smart App Control vs Application Control in a cloud-native world

Smart App Control is a new feature in Windows 11 22H2 that allows only certain trusted, verified and reputable executables, DLL files and MSI installers to run. Anything not trusted will be blocked from running. This leaves us with a very high security posture.

Microsoft says this feature is intended for consumers and small businesses – and recommends larger organizations and enterprises to use Defender Application Control, which uses the same technology in the background, and has been available since the launch of Windows 10.

This blog post covers Smart App Control versus Defender Application Control in a cloud-native world, where Windows devices are connected only to Azure AD and Intune.

Background

One thing to start with – forget AppLocker as it is too weak and has too many flaws. We need something more secure that also includes anything running on the machine, regardless of user space vs kernel space and also applies to local administrators. At the same time, it must be hard to circumvent which is true for both Smart App Control and Application Control. AppLocker is too easy to circumvent, for instance by using a trusted process by AppLocker to load a malicious DLL file. See a number of examples on AppLocker bypasses here.

High-level overview

Smart App ControlApplication Control
Target audienceConsumers and small businesses.Organizations and enterprises.
ModesOn (Block), Evaluation (Audit), Off.Audit or Block mode.
ExceptionsNo exceptions possible – you are 100% in hands of Microsoft control and deciding what is trusted and reputable.You can create exceptions; however, it involves a certain amount of administration and manual work.
EnablementOnly for fresh deployment/installations, or resets of Windows 11 22H2.Any given time – whenever you choose to deploy it.

Goal is to set On (Block) mode, but first Evaluation (Audit) mode

Whenever enabling a technology that will effectively block stuff, it is highly recommended to first assess the situation obtaining intel about what would happen if we set a feature like this in On or Block mode.

So, our goal is without a doubt to first audit and collect information that we can use to evaluate how enabling either Smart App Control or Application Control in block would work. This is the focus to come, when we look at options on enabling audit/evaluation mode.

At the same time, we need to weigh in that running in audit mode gives us no raised security, it will only collect information. The sooner we can enable Block or On mode, the better.

Options to enable via Intune

Smart App ControlApplication Control (AppLocker CSP)Application Control (ApplicationControl CSP)
TechnologyRegistry value1.Endpoint Protection configuration profile (uses AppLocker CSP in background).Using Custom OMA-URI configuration profile using ApplicationControl CSP.
Mode of allow control featuresDefault Allow Microsoft binaries + Intelligent Security Graph (reputable binaries) + Microsoft recommended driver block rules + Microsoft recommended block rules (with exception of what is noted here)Default Allow policy in Audit or Block mode. “Optional” to use Intelligent Security Graph (reputable binaries), but if you want it to work and not block you from working you MUST use Intelligent Security Graph. Custom policy which might contain any number and type of rules, including Intelligent Security Graph.
Managed installerNo, not available.No, not available.Yes, this is possible. You can set Intune agent as Managed Installer to trust everything that comes through Intune. However, Managed Installer can only be applied via a custom created AppLocker XML file which must be applied with an AppLocker PowerShell command, plus the Application Control must use option 13 which is the “Managed Installer” enable switch.
RebootNo, not when applied but requires a reboot to take effect.When applied it forces a reboot of the computer, both in audit and block mode. This breaks ESP (Enrollment Status Page) when using Autopilot. No, not when applied, but needs a restart to take effect (unless you specify option 16 when creating the policy).

1 Registry value to configure Smart App Control is found in HKLM\SYSTEM\CurrentControlSet\Control\CI\Policy. The DWORD value named VerifiedAndReputablePolicyState can be set to 0 = Off, 1 = On or 2 = Evaluation.

AppLocker CSP vs ApplicationControl CSP

The big difference is that the AppLocker CSP always requires a forced reboot, which means we cannot use it in practice when doing Autopilot and using the Enrollment Status Page. That leaves us with manual configuration of Application Control via ApplicationControl CSP, which is the most secure option where you are in total control. The only problem is that this involves many manual steps, and this surely needs a user interface (in Intune).

“WDAC policy deployment via the AppLocker CSP will continue to be supported, all new feature work will be done in the ApplicationControl CSP only”

https://learn.microsoft.com/en-us/windows/client-management/mdm/applicationcontrol-csp?source=recommendations

Example policies and check if policy is applied

You can check what policies are applied, if any on your computers, by looking at two places in the file system. If only one single policy is applied, which is the case if using Application Control with AppLocker CSP, it will be found in the below directory and names SIPolicy.p7b:

C:\Windows\System32\CodeIntegrity\CIPolicies

However, if multiple policies are applied, which is the case if you applied Smart App Control or using ApplicationControl CSP with base and supplemental policies, they will be found in:

C:\Windows\System32\CodeIntegrity\CIPolicies\Active

You can also start msinfo32.exe and see the current configuration.

Caption from msinfo32.exe

Analyzing potential impact of Smart App Control or Application Control

Regardless of if you enable Smart App Control in Evaluation mode or Application Control in audit mode, you can and must follow-up in Microsoft 365 Defender portal (https://security.microsoft.com). This is where you find everything you need to get an overview of the current situation.

Timeline

If you go to a specific device in the Defender portal (https://security.microsoft.com), you can explicitly see the actions by Application Control (and Smart App Control).

Device timeline showing block actions for this particular device.

KQL – Advanced hunting

To be able to get the big picture in a larger organization we need to use advanced hunting to get all the information we can about the audit events.

Smart App Control or Application Control in Evaluation / Audit mode

Use the following KQL query to list everything that would be blocked if switching the Smart App Control to On or Application Control policy to Block mode.

DeviceEvents
| where ActionType == "AppControlCodeIntegrityPolicyAudited"

Smart App Control or Application Control in On / Block mode

Use the following KQL query to list everything that is noticed by users that is blocked when running in On or Block mode.

DeviceEvents
| where ActionType == "AppControlCodeIntegrityPolicyBlocked"

To execute these KQL queries, head over to security.microsoft.com and go to Hunting > Advanced hunting and run the query and note the results, see below example:

Blocked actions, i.e. files that were prevented from being executed.

Getting from audit / evaluation mode to Block / On

Getting from Evaluation mode to On when using Smart App Control is technically easy – but the limitation is that you cannot create any exceptions if necessary. This basically means that you will be forced to live with some things being blocked, provide other means of delivering that app such as via Cloud PC, or simply disabling Smart App Control. In the best of worlds, having Smart App Control in On mode from day 1, let it be only for some or almost all devices is a huge security gain.

Getting from Audit mode to Block for Application Control requires some work as you will have to create the baseline policies and test, test and test before deploying full scale.

Something to note here as well is that when using Application Control, it is a strong recommendation to have the policies signed with a code signing certificate to provide the best security, i.e. protect the policy or policies from tampering by users or administrators. The code signing recommendation also adds some complexity to the process and routines around handling the signing itself.

Summary

I agree with Microsoft that Smart App Control is limited when it comes to exceptions and that Application Control is the superior technology to use. However, as it looks right now, there are no shortcuts to using Application Control and for most organizations, the threshold to pass to get to a block mode today is extensive and very time-consuming. At the same time, there are technical implementations that break most Autopilot scenarios which is not OK to step aside from.

What I really like about Smart App Control is that you get it for free when fresh installing or obtaining Windows 11 22H2 machines, having the ability to easily turn on the protection mechanism that will truly protect your devices. And you can start monitoring from day 1, and with minimum effort easily enable the protection mechanism.

The big drawback of Smart App Control is that you cannot make any exceptions if something is blocked and you want to allow it, that is very obvious. In this scenario you would have to disable Smart App Control or present the application to the users in another way, via for instance Azure Virtual Desktop where you could publish the application as a remote application.

So, what Microsoft should provide are the tools that will help IT departments to enable Application Control. There must be an easy way via Intune to 1) making sure we have an easy way of defining the Intune agent to become a managed installer and 2) making it easy to create a great baseline policy, and 3) making it easy to create supplemental policies whenever something needs to be allowed (as an option to deploying the binary via the Intune agent).

Enrolling shared Hybrid Azure AD Joined Windows devices to Intune

I think this is a really interesting case and although Hybrid Azure AD Join is something I am not recommending over Azure AD Join, sometimes there are circumstances that leads to no other choice but to adjust and make the best out of the situation and plan for a better solution more long-term.

Current situation and scenario goal

The mission is to enroll all Windows devices (shared and Hybrid Azure AD Joined) to Intune and the specifications are as below:

  • Windows 10 and 11 Enterprise 21H2 (or 22H2) computers which are Hybrid Azure AD Joined.
  • The devices are used as shared computers, so there are no primary users of these devices.
  • Intune licenses are device based, not user based which is the typical and most common scenario.
  • Microsoft Endpoint Manager Configuration Manager is NOT used.

The million-dollar question is how these shared computers can be enrolled into Intune automatically? The scenario must cover both enrolling newly deployed computers as well as existing computers. The solution must be fully automated i.e., no manual steps must exist in the process.

Note: The typical GPO to enable MDM automatic enrollment via user credential cannot be used as the users do not have Intune licenses.

Potential solutions

My thoughts on how to come to a solution came pretty much in this order, and turns out to be a real challenge

1. Use “Device Credential” in the GPO “Enable automatic MDM enrollment…”

The GPO “Enable automatic MDM enrollment using default Azure AD credentials” got a new option some years ago and can be set to “device credential” instead of the default “user credential”. Sounds like the perfect solution!

Problem: Error code 0x80180001 in the event logs “Device based token is not supported to enrollment type OnPremiseGroup PolicyCoManaged”. It turns out that this setting is only supported using MEMCM/SCCM or Azure Virtual Desktop, and obviously blocked or not meeting the technical requirements on other machines.

2. Autopilot self-deploying mode profile

That was a good idea although self-deploying profiles cannot be used as it supports only Azure AD Join and not Hybrid Azure AD Join.

3. Provisioning package – Only enrollment

Using a provisioning package (PPKG) you could potentially enroll into an MDM solution (such as Intune) using Workplace/Enrollment settings as noted in Bulk enrollment – Windows Client Management | Microsoft Docs. However, “username and password security type not supported”. However, this enrollment seems to primarily be targeted and intended for third party MDM solutions or the now long gong feature to enroll into on-premises MDM in Configuration Manager, not Intune. Or did anyone succeed in enrolling into Intune this way? If so, please ping me!

4. Provisioning package – Using bulk enrollment token

Although this way is typically used for performing Azure AD Join + automatic Intune enrollment using a Device Enrollment Manager (DEM) account, I thought I’d try it out to see what happens as I never tried this on a Hybrid Azure AD Joined computer.

Well after obtaining the bulk enrollment token through the simple wizard in Windows Imaging and Configuration Designer, I switched to advanced mode and got rid of everything from the provisioning package apart from the Azure/bulk enrollment token parts.

I then ran the provisioning package on my target test machine and the enrollment seem to have worked. Although, it resulted in another device object in Azure AD, and it successfully enrolled into Intune.

Running a PPKG using Bulk Enrollment token on an already Hybrid Azure AD Joined Windows device – this is the result in Azure AD!

Hmm, not ideal but a big step in the right direction. Another question or thought is that even though this works technically, how far from being a supported is this scenario? Intune-device based licensing supports DEM accounts as enrollment type as per Licenses available for Microsoft Intune | Microsoft Docs, and the bulk enrollment is supported as well as per Enroll devices using a device enrollment manager account – Microsoft Intune | Microsoft Docs.

Next steps and summary

Well, automating the application of PPKG from step 4 above as part of the deployment process is easy, it needs some additional checks though as the provisioning package must only be run after the successful Hybrid Azure AD Join has taken place, otherwise I see this will fail. Not optimal and requires more testing, and even if this would work the scenario is a true corner-case!

Going back to Autopilot self-deploying mode seems a lot easier, so let’s evaluate what needs to be in place for this to become reality, overcoming the hurdles!

A modern Windows client platform connected to Azure AD and Intune only is the future – here is why you should start testing today!

By connecting your Windows devices solely to Azure AD and Intune you will improve the work lives of for your users and make it easier for you in IT to manage the platform during the device lifecycle.

Windows devices in the future are no longer connected to a traditional Active Directory, and they are not managed by Configuration Manager or other on-premises management tools, and not with Group Policies. The Windows devices of the future are independent of your datacenter which means IT can focus on improving availability of the resources the end users are dependent on in their daily work, which are applications, tools, and information.

End user experience and challenges today

Are you and your end users sick and tired of the fact that starting and logging into Windows takes several minutes? One common cause for this is a legacy of many years of GPOs and scripts that are executed at start and logon.

Do your end users still need to come into the office network to get all updates, configuration or changing password? This is something that becomes a non-issue in the cloud-only world. Even though these types of needs have decreased because of the pandemic I still see and hear about this too often.

Improving end user experience and simplifying are the keywords

The reasons of going cloud-only on your Windows devices are very much about significantly improving your end user experience, and at the same time making it easier to manage for you in IT. To continue doing what many organizations are doing today, i.e., managing Windows with existing on-premises AD and GPOs, running devices in Hybrid Azure AD Join state plus adding co-management and Intune just makes your life in IT more complex and harder, and give your end-users very few benefits to be honest. Everyone would gain from letting go of on-prem AD and traditional managing software such as Configuration Manager.

Microsoft recommends going cloud-only and not staying in hybrid mode

The fact is that Microsoft is recommending the hybrid scenario only as an interim solution for existing devices. For new devices Microsoft are very clear that they recommend cloud-only devices.

Keep in mind that while Microsoft fully supports hybrid Azure AD join, we designed this capability as an interim solution for existing endpoints. We strongly encourage customers to begin their planning and implementation of full Azure AD-joined systems as soon as possible.

Source(s): Success with remote Windows Autopilot and hybrid Azure Active Directory join – Microsoft Tech Community and Planning for cloud-native Windows endpoints and modern management – Microsoft Tech Community

The most common myth killed once and for all – access to on-premises resources

The fact is that most organizations still have, and will have for many years to come, user resources in their datacenter on-premises. How do users get access to file share, printers, and applications on-premises when the Windows device is only in the cloud? With Windows Hello for Business Cloud Trust or FIDO2 security keys, this has never been easier to setup and enable!

Pros for cloud-only Windows devices

  • Performance and user experience. Microsoft’s former corporate vice president for Microsoft 365, Brad Anderson, compared his iPhone to a cloud-only Windows device s few years ago. The Windows device started and became usable faster than an iPhone. That is a notable example that still is valid. Mobility, speed, and battery life is something the users really appreciate.
  • Reduced complexity. What I see is that customers that are running in the hybrid scenario has a complex day-to-day life in IT, in terms of managing and troubleshooting. You have two environments to take into consideration all the time which makes things sometimes twice as hard or take more time than it should to achieve the goal at hand.
  • More time for valuable work. How much time do IT spend on keeping the basic infrastructure working? By that I mean specially Configuration Manager which always have had problems with agents, driver packages becoming corrupt after working for years etc. I have through my years spent too much time on just keeping things at a working level, it is time to bury Configuration Manager and spend this time on more valuable work such as follow-up and proactiveness.
  • Get rid of your legacy. Most organizations have over the years migrated to a number of Windows client platforms, from Windows 2000, XP, Windows 7, to Windows 10 and soon Windows 11. What most organizations have in common is that the same GPOs and scripts are still being applied although first configured 15 years ago, even though some policies have been cleaned out through all migrations. Switching to cloud-only is the perfect fresh start of getting rid of all your legacy stuff and start building on something new!

Cons for cloud-only Windows devices

  • Not for everyone. Being able to utilize Microsoft cloud services is a pre-req of course. To be honest, there are more challenges that could block an organization from going cloud-only. Things such as 802.1x can be a challenge and specific requirements around security another. The point is, if you do not even try you will not know what to solve or what Microsoft will eventually deliver in their product and services to solve your blocker. Adding cloud-only Windows devices to your roadmap and work on dependencies is essential in making progress.

How to get started?

So how do you get started? In its simplest form, start with Autopiloting (Azure AD Join + Intune) the device and then perform all your day-to-day work on a cloud-only Windows PC. After that start solving the challenges that you face, creating a configuration baseline and deploying applications that you need. Some challenges will be harder to pass than others, and some might be blockers. The point is, without starting your journey toward a future cloud-only future Windows device you will not know what to fix and what to talk to for instance the network team about.

Microsoft has a good starting point at Get started with cloud native Windows endpoints – Microsoft Endpoint Manager | Microsoft Docs.

Summary

To summarize, the future is to have your Windows devices connected cloud-only Azure AD and Intune. That has great advantages for end-users as well as IT. The fact that Microsoft themselves are living by this already, and the fact that they point customers towards this direction and in combination with all benefits should make this decision easy.

Profile management overview in Windows – how to get back to a working state after a reinstall or reset (or renewal of device)

This is a high-level summary of the specific needs, business impact and listing of current profile management options for your physical and virtual Windows 10 and 11 devices. The focus is how to get back to a state which can make you productive as soon as possible after a device reinstall or reset. This scenario of course also covers when you get a new device that replaces an older one.

Business impact

Most organizations have a policy that “we will troubleshoot a problem on a Windows device for X number of minutes, if we can’t solve it, let’s do a reinstall or reset”.

This might seem like a great policy that saves time for the service desk. But the numbers the management do not see is how much time have service desk have to spend on helping the user get back on track after the reinstall or reset? The same goes when user needs help transferring from one device to another as part of regular renewal of device. The potential time-saver here is enormous. If the user can get to a state that has everything the user needs available instantly, the user can become productive much quicker.

A consequence of having everything brought back quickly is that not only can the user be productive quicker, but the user will much more likely agree to a reinstall or reset when knowing the user can start working without hazzle again. It might also mean that you can reduce troubleshooting time from say 60 minutes down to 15 before you do a reinstall or reset. Overall a real time-saver and money-saver!

Needs and goals

High-level goals:

  • Getting back to a state where a user can start working as soon as possible after re-install or reset of the device, or even when switching device as part of hardware renewal.
  • “Everything back as it was” (more details on this below). I.e., the time the user needs to spend on getting back to a state that just works as before needs to be minimized.

Expanded description of goals:

  • All files and documents back as they were and accessible by user.
  • All required applications back as they were. (This is out of scope for this blog post as most organizations use ConfigMgr, Intune or a third-party software to deploy applications).
  • All relevant settings back:
    • Specific settings for line of business applications.
    • Outlook signatures and calendar settings etc.
    • Printers and printer settings.
    • Browser related settings, favorites, and history, including saved passwords.
    • Mapped SharePoint sites (Teams files) in File Explorer.
    • Settings for apps.

Solutions

Let’s have a look at what Microsoft technologies are available to solve the needs.

Personal files and documents

  • OneDrive for Business with Known Folder Move.
    If you have the possibility to use OneDrive for Business this is the best solution out there. Make sure to set the GPO or MDM setting to silently configure OneDrive to automatically have your OneDrive folder available after re-install or reset. Also set the policy setting “Enable Known Folder Move” to make sure that Desktop, Documents and Pictures folders are redirected to your OneDrive Folder. Reality check, do you know anyone who do NOT save stuff they need on the desktop? :)
  • Work Folders (which I typically call the internal OneDrive).
    Setting up Work Folders is easy, the role has existed in Windows Server since 2012 R2, thus requires a Windows File Server to setup and enable. Once you’ve setup Work Folders, use good old redirection of Documents and Desktop folders (and maybe Pictures as well) pointing to the local Work Folders directory just like it is done with Known Folder Move for OneDrive for Business.
  • Folder Redirection + offline files.
    Only two words: Stay away! (And migrate as soon as possible to OneDrive for Business or Work Folders if you are already using it). For some organizations I have worked with I have made it opt-in to use offline files, clearly stating the potential risks when opting in. Offline files cause user problems and have very high risk of user data loss.

Common or shared files and documents

  • SharePoint Sites (Teams files directories).
    Many users prefer to work with SharePoint sites and Teams files by syncing them to work with the files in File Explorer. There is no official way of having these remapped automatically after a reinstall or reset of a Windows device.

Settings

  • User Experience Virtualization (UE-V).
    I have many times referred to UE-V as the best thing since sliced bread. It is a technology that was released for about 10 years ago, with the intent to provide roaming of settings for Windows and applications (both Microsoft and any third party), using on-premises file shares. It also roams printers if you are not deploying those through other means.

    Since Windows 10 version 1607 UE-V is integrated in the operating system. I’ve used UE-V quite a lot and this is a really good technology to get many settings back after a reinstall. In one case I could do a F12 reinstall of a Windows 10 device before going to lunch and after lunch I logged in and started working instantly, with all settings back. Those were the days!

    Over time as applications are moving to the app’s world, UE-V has basically become less effective in its job. Also, after adding UE-V to Windows version 1607, UE-V has not gotten much love from Microsoft and as no development has been made for almost six years this is still something that most will benefit from, but sad to see that Microsoft do not care for this.
  • Enterprise State Roaming.
    About the same time that UE-V was integrated into Windows 10 we also saw the introduction of Enterprise State Roaming. This is a technology that use the cloud (a private protected and untouchable area) in Azure to store profile settings that roams with the user. For instance, background image, Windows theme settings and some other stuff is being roamed when enabling this through Azure AD. Sad to say, this feature is facing the same destiny as UE-V, with no new features or changes for the last six years or so.

    Actually with Windows 11 the number of settings that roam using Enterprise State Roaming have decreased, now only roaming passwords, some Windows settings, and language preferences.
  • FSLogix profiles.
    Microsoft bought FSLogix and with that obtained their profile technology. This is a container-based profile solution used primarily in remote Windows solutions, such as Azure Virtual Desktop. Although the technology should be possible to use on physical machines as well, I haven’t many details regarding this and haven’t tried it our myself. One reason for this is that FSLogix profiles requires an Active Directory and is not yet (per January 2022) supported for Azure Active Directory, although this is announced in the future.
  • Edge profile sync.
    The new and lovely Edge has profile sync with roaming built-in which is very much appreciated. Sign in with your school or work account and off you go! You’ll also find some additional information on Configure Microsoft Edge enterprise sync | Microsoft Docs.
  • Outlook settings roaming.
    Finally you can roam your email signature and a bunch of other settings to the cloud – without doing anything other than making sure this option is enabled. Take a look at Outlook roaming options to get more information about this one.

Note 1: Roaming profiles take care of both files and settings but like with folder redirection and offline files: Stay away from roaming profiles to make your life happier.

Note 2: As apps in Windows always store their configuration and user specific data in a standardized location. That is C:\Users\%username%\AppData\Local\Packages\%AppName%\ which means Microsoft should be able to provide a supported way of roaming these settings.

What settings can you use?

Depending on how your Windows devices are managed you can use some or all these technologies. This is applicable for Windows 10, Windows 11, Windows 365 as well as Azure Virtual Desktop. Note: All technologies below are not necessarily supported for all physical and virtual use cases.

Active Directory JoinedHybrid Azure AD JoinedAzure AD Joined
User Experience Virtualization (UE-V)Yes, pointing to file shareYes, pointing to file shareYes, pointing to OneDrive
for Business local folder*
Enterprise State RoamingNoYesYes
FSLogix profilesYesYesNo (not supported yet)
Edge profile syncYesYesYes
Outlook settings roamingYesYesYes
Summary of what profile technologies are available for various Windows device join types.

* For configuration, this is a great start: Manage User Experience Virtualization on the Modern Desktop | Aaron Parker (stealthpuppy.com)

Support matrix

Windows 10/11 – PhysicalWindows 10/11 – VDIWindows 365Azure Virtual Desktop
User Experience Virtualization (UE-V)YesYes**
Enterprise State RoamingYesYesYesNot supported**
FSLogix profilesNot supportedYesNot supportedYes***
Edge profile syncYesYesYesYes
Outlook settings roamingYesYesYesYes
Summary of what profile technologies are supported officially by Microsoft.

* Technically it will work, but likely not supported by Microsoft for Windows 365 nor Azure Virtual Desktop.
** Supported only for personal pools – not multi-session Windows 10 or 11, nor Windows Server.
*** For Azure Virtual Desktop, currently there is no support for Azure AD Joined devices.

Summary

With the existing Microsoft tools and technologies, you can reach a state where most of the stuff you want back actually is configured and brought back automatically. Getting the files and documents back is easy. Edge profile sync and Outlook settings roaming are a no-brainer and should be used by everyone.

UE-V and Enterprise State Roaming are not developed anymore but they still fill a purpose and can be very useful to save time, starting today, as they are very easy to get started with and has a very low implementation cost. FSLogix profiles are primarily intended for datacenter hosted solutions.

With those facts, there is a strong need for Microsoft to strengthen profile management to make it the true time-saver it can be. IT management would very much appreciate it I can assure. But the ones that would appreciate this the most are the end users!

Problem with “New User” being the only account on the sign-in screen after reboot

This is one of the most mysterious problems I’ve encountered! Anyone who can provide input is more than welcome to ping me on Twitter or Teams, or help by entering some basic information in this form.

UPDATE September 6, 2022: Update the problem description as the Web sign-in setting is also causing problems using Cloud PC (Windows 365): “Another user is signed in. If you continue, they’ll be disconnected. Do you want to sign in anyway?”. See more below under “Problem #2”.

UPDATE July 6, 2022: A response from Microsoft leads to the root cause being Web sign-in being enabled, which is in preview (and has been for quite a few years) and is also unsupported. Still does not explain the extreme intermittent occurrence of the problem but at least a great indicator and something to validate.

UPDATE July 5, 2022: Added this form to gather and hopefully be able to get to the root cause. Also, I’ve gotten indications on a potential causes leading to the New user state, more below.

Problem #1

You restart your Windows 10 or Windows 11 device (Azure AD Joined + MEM/Intune enrolled) and after the restart, instead of displaying the last logged on user, the only account on the sign-in screen is an account named “New User”.

This happens extremely rarely, but I’ve seen it a few times. The “New User” comes from nowhere and if you click Switch user it just returns to the same view as below.

I have seen the problem a few times for multiple Windows 10 versions back to at least Windows 10 v1909, and on multiple devices from multiple vendors. Unfortunately I’ve seen it once on a Windows 11 device as well. The other day this problem hit a colleague of mine as well so it’s not just me :) .

Problem #2

Cloud PCs established as part of Windows 365, in Azure AD Joined mode, experience the sign-in message that Other user is already logged in, every time when logging in (and even after restart):

Another user is signed in. If you continue, they’ll be disconnected. Do you want to sign in anyway?

Cause

I’ve gotten reports (thanks to the community) with a response from Microsoft leads to the root cause being Web sign-in being enabled, which is in preview (and has been for quite a few years) and is also unsupported.

This is also true for the environments where I have seen this problem occur so this is the most likely cause of the “New user” phenomena causing Problem #1!

For Problem #2 this setting is confirmed to be the problem – as that problem was very easy to reproduce!

Solution

Disable Web sign-in!

Summary

The Web sign-in setting is really treacherous, causing a lof of head ache. I suppose this is the reason Microsoft is not recommending this setting.