Windows 365: Troubleshooting guide
Introduction
This is the seventh part of the Windows 365 series on my blog which is dedicated to troubleshooting of Windows 365. In this post I will walk through different scenarios, where issue could occur and how to solve them accordingly. This is your booklet for Windows 365 troubleshooting 😁

Why Troubleshooting?
It must be said, that Windows 365 is a very simple service and super user-friendly, issues are quite rare. However, if things go wrong, you might want to have an extensive guide on what you should check to restore normal service operation. This post holds a lot of ideas and troubleshooting advice for different situations.
Identifying the source 🔍
First of all, you should identify the source of the issue. Some of the issues are related to each other, however in the end we have 5 main technologies that come to play when accessing and operating Cloud PCs:
- Windows 365 > service, platform, provisioning policy - most provided by Microsofts responsibility
- Intune > endpoint management, policies, apps, compliance signal, feature configuration of Windows
- Windows > operating system base (although it is customized for W365), includes everything the user interacts with
- Entra ID > identity & access perimeter, includes all about authentication both to the services as well as on the OS
- Network > external network, from which the client/user is approaching to connect to the Windows 365 service, as well as the network to which the W365 machine is connected to (Azure network connection or Microsoft hosted network, read more)
At a glance: most common issues ⚠️
- Network connectivity
This is probably always the issue: the network 😉 To check if it is really network and the Microsoft service endpoints for W365 are impacted, make sure you switch to another device and another network and try if you can connect to your Cloud PC from there.
- User has no W365 license assigned
Simple: the user has no Windows 365 license assigned (anymore) and therefore his Cloud PC is set to grace period and the connection to it will not be possible anymore.
- W365 machine was reset or is still provisioning
Patience is key, make sure the Cloud PC was fully provisioned and is not currently resetting. You can check the status of the Cloud PC from the Intune console at the overview.
- Entra ID (Conditional Access) blocks authentication
If connection approaches are blocked, looping or not even processed, this may be due to an Entra ID restriction. Maybe check, if the user is still healthy and enabled and is not blocked by any Conditional Access policy. You can identify this by having a look at the sign-in logs of the user and see if there are any interruptions or failed sign-ins to the Windows 365 service.
- Provisioning policy malfunction
Provisioning policies are the starting point to your Windows 365 machines. Any deletion or manipulation of the policy, or maybe group "unassignment" will have severe impact on the functionality of provisioned and new Cloud PCs.
- Client issues with the connection in Windows App
Maybe there is an issue with the client app that tries to establish a connection to the Cloud PC. To eliminate this, make sure you try to connect from a different source like the browser at https://windows365.microsoft.com/
- Intune policy misconfigurations in security area
This is a hard one. An Intune configuration or endpoint security policy maybe prevents the functionality or even pure connection to the Cloud PC. I would point to security policies that have such a severe impact. To make sure it is not caused by something like this, exclude your Cloud PC from the potential or all Intune policies.
- Any prerequisites not met
Please always ensure, that you meet all the prerequisites - for that please check out my full technical design blog:

Easiest and fastest fixes ✅
The following tasks can be done primarily by an Intune administrator and have high influence to the functionality of Cloud PCs and may result in healthy operation after an issue:
- Reboot the Cloud PC / eliminate OS issues
- Switch device, network and client app from where you are connecting from / eliminate network, device or app issues
- Restore, reprovision or reset the Cloud PC / eliminate OS and platform issues
- Remove and add the Windows 365 license to re-initiate the service for the user / eliminate platform issues or user issues
- Exclude the user from potential blocking identity measures like Conditional Access or require re-register Authentication methods / eliminate issues from the identity
- In case of Azure network connection: switch to Microsoft hosted network / eliminate network issues
- Exclude Cloud PC from Intune policies / eliminate issues with the management plane
As enduser
End user have some management options (if configured in user settings in Intune by an admin). They can restart, reset or restore the Cloud PC. Connection inspection may helps to identify issues with the network and connectivity.

Monitoring 🕵️
When it comes to monitoring, you have quite some options by leveraging Intune. The Cloud PC in Intune shows all applied profiles, apps and more reporting information. Make sure to check the status of the Cloud PC, as well as the object in Intune. You could also collect diagnostics via Intune remote task, however this will only collect logs that are related to the MDM stack.



Performance issues 🏎️
Performance shall also be mentioned within this post as this is maybe also something that users complain and confront you with. Besides the traditional methods to measure metrics (Event viewer, Performance Analyzer, Stopping time, reviewing logs) you can also take advantage of the built-in reports of Cloud PCs in Intune. This is possible per device or at Intune > Reports > Cloud PC overview. Have a look at the following reports:
- Connection quality > How good and healthy was the connection to Cloud PCs, approached by consumers
- Cloud PC utilization > For how long where the users connected to their Cloud PC
- Cloud PC recommendation > Recommendation based on the Cloud PC utilization, where Intune shows you recommendations to switch the SKU and resize the Cloud PC with resources




Cases 🗃️
Network issues
Recently I had a very complex situation (at first look), where somehow no connection to my Cloud PC could established. I was trapped in a service loop and couldn't connect a Cloud PC, neither from the app, nor browser. I tried to reset everything and guess what; in the end my network was somehow blocking service connection and connectivity.
BitLocker or drive encryption
Windows 365 is not compatible with BitLocker or any other drive encryption. Don't approach any encryption.
Authentication loop
When something goes wrong during authentication, or you even end up in a loop while connecting to the Cloud PC, I would recommend to switch to the browser first and try again. If it is still the same issue, I would delete and re-register all MFA methods for that particular user and make sure Conditional Access (token protection) doesn't interferes.
Sign in failed, disconnected
When your issue states "Sign in failed. Please check your username and password and try again." You might check out the Entra SSO feature in the Windows 365 provisioning policy. Enable/disable and apply it again. Also make sure to change your client app and network in this situation.
Last resort: Microsoft support
Sometimes it can occur that there is a bug in the service or software itself, provided by Microsoft. Then a customer can't change whatever is going on in the background. When you are sure that you eliminated all issue sources, you may reach out to the Microsoft support, or 💡 even better: your Microsoft Account team, CCP, CAT or others.
powered by Oceanleaf
