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Last month, we shared tactical insights and recommendations on how to shift your existing environments to deploy Windows 10 feature updates to remote endpoints using Windows Update for Business in order to roll out updates more consistently and with greater automation.

Today, we want to complement this approach with the introduction of a Windows servicing calendar and by providing you with guidance, whether you use on-premises or cloud-based tooling, on the changes you might want to consider for your environments and when those changes should be rolled out.

The calendar helps you shift your Windows 10 servicing cadence from a project-based effort to a more fluid process that aligns across the release cycles of Windows, Office, and endpoint management tools, such as Configuration Manager. Additionally, it provides recommendations on how to modernize your environment to move to a data-driven servicing model and showcase new capabilities to users. If you are using Windows Update for Business today, our guidance is to maintain that approach and review this article for insights on how to schedule configuration changes and improve the user experience during deployment.

Let’s get started.

To many organizations, applying Windows 10 feature updates requires more than just deploying the feature update to endpoints–common tasks include updating the supporting infrastructure and configurations, validating applications before broad deployment, and assessing new features. For this reason, the calendar template incorporates information on when to update the dependencies most common across commercial  organizations to support Windows feature updates, including Microsoft 365 Apps, Microsoft Endpoint Configuration Manager, and Microsoft Security Baselines.

Microsoft’s strategic guidance around Windows as a service has remained constant:  plan, prepare, and deploy. This article maintains that approach and adds guidance and timing considerations to each of the plan, prepare, and deploy phases. Four additional consistent focus areas can be identified across each of the plan, prepare and deploy phases, which are:

  • Compatibility. Validate application and device compatibility between feature updates.
  • Deployment. Ensure infrastructure, configuration, and operational readiness for feature updates.
  • Capability. Realize value from feature update improvements.
  • Modernization. Reduce time, effort, and cost of servicing through process or tooling improvements.

To get the most value from this article, you should familiarize yourself with the editions of Windows 10 in your environment and read through the entire process. Then, using the recommendations and supporting material in each phase, align to one (or more) calendar cadences aligned to your business need, or integrate the recommendations into your existing servicing process.


Windows delivers innovation with improvements to servicing, security, performance and productivity with every release. While we encourage  organizations to strive towards deploying every release to at least some portion of their estate, we also recognize that  organizations with very high device counts, and the need for no/low disruption environments will choose to update less frequently.

The modern calendar approach can be used for servicing across Microsoft products and services in a way that is flexible for your business needs and accommodates a faster or slower cadence of innovation adoption. Currently,  organizations of all sizes use different cadences for feature updates. Typically,  organizations default to adopting a feature update annually that is serviced for 30 months. As  organizations modernize their environment and update processes, they become more comfortable with accelerating to adopt feature updates as they become available, to an increasing portion of their estate. For further information on how all feature updates are serviced, please see the Windows lifecycle fact sheet.

Performing Windows 10 feature updates less often than once annually has the potential for devices to go out of service and be vulnerable to security threats, as they will stop receiving monthly security updates. Organizations that are typically blocked from updating annually experience slow, fragmented application testing across their business, must wait for a critical ISV to release a support statement, encounter unwillingness from regional IT to “disrupt” users, or have limited endpoint connectivity to perform an update. Organizations that experience these blockers should use this guide to find opportunities to optimize their processes, and use the Enterprise / Education editions of Windows 10 for its extended servicing benefits. Organizations are also encouraged to modify timings as needed across each phase to address resource availability, one-time deployments of infrastructure that support the servicing motion, or deployment duration for larger organizations that have over 50,000 Windows endpoints.  

Choosing the right calendar

This article presents two calendar options for consideration to help commercial  organizations align with Windows. Depending on the volume of endpoints you are updating, deployment timelines will vary and should be stretched based on your business need and the amount of servicing provided by the edition of Windows 10 used in your organization. We recommend reviewing each option and then consider what a default servicing cadence will be for your organization and then what portions of the business can or would benefit from a quicker cadence, based on worker persona type, business function or location.    

Annual – Apply one feature update every calendar year

The calendar below shows an example schedule to apply one Windows 10 feature update to a commercial environment, aligned to Microsoft Endpoint Configuration Manager and Microsoft 365 Apps release cycles:


Figure 1. Annual cadence

The calendar above uses a rolling 12-month update cadence to update all devices, meaning that all devices will receive one feature update annually. For some  organizations, deployment may take longer than the three-month window provided, and will result in an enterprise having two versions of Windows 10 in the estate. By aligning to the Windows 10, version H2 feature update, Enterprise and Education editions of Windows 10 will be serviced for 30 months from the time of availability, giving commercial  organizations with these editions more flexibility when applying future feature updates.

Enterprises who selectively deploy Windows feature updates on this cadence have the following characteristics in common:

  • They are starting their journey with the Windows 10 servicing process – for those unfamiliar with new processes that support Windows 10 servicing, moving from a once every 3-5 year project to a twice per year feature update process can be daunting. Using a once a year approach with new tooling can be the right choice for  organizations that want to learn new approaches and tools to reduce effort and cost.
  • They can’t handle a rapid deployment cadence for all of their endpoints and apply this cadence to all or a portion of their environment.
  • They want to wait and see how successful other companies are at adopting a Windows 10 feature update – some  organizations prefer to have extra assurance before planning to deploy.

Rapid – Apply each feature update as it is released

Once enterprises are familiar with deploying feature updates on an annual cadence, shifting to a rapid cadence is often possible with minor increases in effort, as plan and prepare motions are well established. When coupled with lower update deployment times through improvements in how updates are applied, a rapid cadence is within reach for enterprises of any size. The diagram below shows the update cycle that can be applied to service Windows on a rapid cadence, and the service duration that each feature update provides when implemented.


Figure 2. Rapid cadence

Enterprises that benefit from the rapid servicing process have the following characteristics:

  • Stay evergreen and continuously update supporting infrastructure to unlock new working scenarios
  • Consist of a large information worker persona population that can use the latest features and functionality that Windows and Office Provide
  • Have experience with previous Windows 10 to Windows 10 feature updates
  • Already apply updates annually and have identified opportunities to deploy updates quicker to a portion or all of their environment.
  • Have developed processes that can enable portions of the estate to run on separate cadences – for example, some parts of the business may value innovation more than others, and can adopt at quicker speeds.

Calendar dependencies

Organizations can expect to update infrastructure dependencies on the following schedule for each cadence:


Figure 3. Infrastructure and configuration dependencies

For  organizations that plan to apply one or both Windows feature updates each calendar year, investments should be made across compatibility, deployment, capability, and modernization. For  organizations looking to reduce the amount of effort needed to apply updates by only maintaining supportability, the majority of effort should be focused on compatibility and deployment activities when feature updates are deployed. This approach is explained in detail in the each of the plan, prepare, and deploy phases below:


Duration – Up to 4 weeks


  • Rapid – Every April, October
  • Annual – Every October

A robust planning stage enables commercial  organizations to:

  • Use a common language to describe criticality of applications and severity of issues
  • Have an agreed set of metrics that define success for feature update deployment
  • Determine what applications and device types should be validated ahead of broader deployment
  • Understand what infrastructure and configuration changes are required in their environment to support the Windows 10 feature update
  • Identify new features in the upcoming release that could benefit users and IT
  • Identify improvements to existing infrastructure or configuration to benefit users or reduce time or effort for future deployments
  • Focus on tasks that simplify deployment
  • Review lessons learned from the previous deployment to reduce time or effort for the next feature update

Recommendations on how to achieve the above outcomes are included below. The duration of the plan phase will vary dependent on how many of the processes or tooling recommendations are already adopted.

Compatibility planning

Commercial  organizations must feel confident that a Windows 10 feature update will not cause interruption to their critical line of business applications. Microsoft is committed to ensuring your apps work on the latest versions of our software, and with Microsoft App Assure, commercial  organizations can receive no-cost app compatibility assistance when deploying Windows 10 and Microsoft 365 Apps with an eligible subscription. The following recommendations build on this confidence for application and device compatibility and help commercial  organizations plan for the next Windows 10 feature update.

Determine what applications and device types should be tested ahead of broader deployment

  • Maintain an application and device portfolio – create a list of what applications are used in the company and maintain it for each feature update. Understanding what device types exist in the estate will help to determine the applications that need to be validated and the types of devices to test with.
  • Assign application owners to critical applications – critical applications should be tested ahead of broad deployment of a feature update. Maintain a list of application owners in the business that can validate or assign testers to critical applications and provide compatibility feedback.
  • Use Desktop Analytics to maintain application data – Desktop Analytics provides a way to assign application importance and ownership in your environment and can reduce the time and effort needed to maintain this information between feature updates.
  • Review and confirm the Microsoft 365 Apps servicing channel for your company
    • Semi-Annual Enterprise Channel – Released in January and July. This channel is selected by default for enterprise  organizations. Users will have to wait a longer time to consume new feature updates. For enterprises with compatibility concerns that deploy a Windows feature update once per year, include the January release into your pilot deployment or delay adoption until the feature update is broadly deployed, and test office apps separately.
    • Semi-Annual Enterprise Channel (Preview) – Released in March and September. Use this channel to have users receive feature updates quicker than the Semi-Annual Enterprise Channel. Testing of Microsoft 365 Apps on these releases will occur as a separate motion from Windows 10 feature updates.
    • Monthly Channel – If your environment does not have critical line-of-business applications, add-ins, or macros that need to be validated to determine if they work with an updated version of Microsoft 365 Apps, the Monthly Channel is the best way to provide new features to users in the quickest way. Rapid adopters of Windows are encouraged to use this servicing channel.

Use a common language to describe criticality of applications and severity of issues

  • Define what applications are critical, important, and not important – setting common terminology for critical and important applications helps to make decisions if/how applications should be validated and what course of action to take if the application has a compatibility issue during deployment.

Have an agreed set of metrics that define success for feature update deployment

  • Determine success criteria to move from the prepare phase to pilot deployment and then to broad deployment – Understanding the number of applications that must be validated in the prepare phase, and then understanding what is an acceptable pass rate for critical and important applications, is crucial to determining when to move to a pilot or targeted deployment, and then a broader deployment. Agreeing on these metrics up front in the planning phase ensures that decisions are made based on data, rather than opinion.

Deployment planning

In order to deploy at scale, IT Admins need to ensure their deployment engine is ready. This includes making sure the infrastructure and security applications are up to date with supported versions. Any new training for support teams should also be planned at this stage. The recommendations below help commercial  organizations to be successful during deployment planning:

Understand what infrastructure and configuration changes are required to support the Windows 10 feature update

  • Assess the infrastructure used to deploy and manage Windows 10 – Confirm the support of the new feature update with your infrastructure management tooling, and determine the effort needed to update the infrastructure.
    • The most recent branch release Microsoft Endpoint Configuration Manager will support all in-service versions of Windows 10, and the next Windows 10 feature update.
    • For those  organizations that use cloud-based infrastructure management tooling such as Microsoft Intune with Windows Update for Business, supportability challenges will be reduced as no on-premises or client-side products need to be updated.
  • Plan for updates to Windows 10 administrative templates & security baselines – To navigate the large number of controls, organizations need guidance on configuring windows features and security controls. Microsoft provides this guidance in the form of administrative (ADMX) templates and security baselines, which are updated per release of Windows. It is recommended that administrative templates and security baseline updates are applied per feature update to protect all Windows 10 endpoints in your environment.
  • Review supportability for security agents installed on Windows 10 – For  organizations with non-Microsoft security tooling installed on Windows endpoints, confirm with the 3rd party supplier what updates are required to security agents to be supported on the next Windows 10 feature update.
  • Review how planned changes to infrastructure and configuration will impact support and operations teams – document new features, configurations, or working scenarios provided by the required changes above, and provide a summary to your support and operations teams to ensure they can assess any impact.   

Have an agreed set of metrics that define success for feature update deployment

  • Determine success criteria to move from the prepare phase to deployment phase – ensure tasks such as updating infrastructure and configuration are defined and validated ahead of pilot and broad deployment.

Focus on tasks that simplify deployment

  • Don’t spend time designing deployment rings (at this stage) – often, commercial  organizations spend effort up front to design a deployment ring strategy for all endpoints without understanding what compatibility challenges exist. Save this effort for the deploy phase when more is known about the environment.

Capability planning

The deployment of a Windows 10 feature update alongside updates to infrastructure, and configuration and productivity applications unlock new features and working scenarios for users and IT. Teams should be aware of new features or functionality that help streamline the deployment and make the end user experience better. The constant innovation in the servicing stack of the OS, or with Configuration Manager and Intune may provide added benefits to the deployment that weren’t previously available. Capability planning should be focused on improving user experience, maintaining productivity, and minimizing user interruption during the update process. The following recommendations help to provide structure to these outcomes:

Identify new features in the upcoming release that could benefit users and IT

  • Review IT Pro features of Windows 10 – The what’s new in Windows 10 page lists improvements for IT Pro’s across several areas including but not limited to Servicing, Security, Virtualization, Deployment, and Accessibility. Reviewing these capabilities against your current environment can help to determine where future investments can be made.
  • Review Windows 10 TipsWindows 10 Tips provides new ideas for getting the most out of Windows 10. New features or functionality may help users find simple ways to perform existing tasks, which can help reduce the number of custom applications needed to support functions.
  • Leverage the Windows Insider Program to test proposed features in future releases – In the planning phase, register for the Windows Insider program to review proposed features for upcoming Windows builds.
  • Join the Windows 10 TechCommunity – Learn about technical best practices, tips and tricks, and the latest news and trends related to Windows 10 and the Windows client OS at TechCommunity.

Modernization planning

Windows servicing can be improved through efficiencies in process and adoption of Microsoft cloud tooling. Planning for modernization of the Windows servicing process will be dependent on a commercial customer’s ability to optimize internal deployment and testing processes, and consume cloud services that improve the Windows servicing experience. Often, commercial  organizations see the benefit of tooling to improve the process but may not be able to immediately take advantage it due to technical debt or industry regulation. The following recommendations can assist commercial  organizations understand where to invest effort to improve the process:

Review lessons learned from the previous deployment to reduce time or effort for the next feature update

  • Review lessons learned from previous deployments of Windows 10 to discover bottlenecks in existing processes / tooling – There is no substitute for going through a process to understand where delays to the process can occur. Examples include effort for manual testing of critical applications, creating images for use in new device builds ahead of validated deployment, or delays in obtaining supportability for important (but not critical) applications.


Identify improvements to existing infrastructure or configuration to benefit users or reduce time or effort for future deployments

  • Assess current state capabilities across compatibility and deployment – Reviewing these capabilities against your current environment can help to determine where product benefits can help to address delays.
  • Prioritize investments to that reduce time, cost, or effort – products such as Desktop Analytics, Windows Update for Business and Delivery Optimization can help speed up adoption of Windows for commercial  organizations, but benefits of the tools/features will not be seen if a customer has a limited set of applications, or high-capacity network links that can distribute feature updates to endpoints. In some cases, finding ways to reduce application validation via automation or finding a way to accelerate change control process can provide equal impact to reduce time to adoption.


Duration – Up to 8 weeks


  • Rapid – Every May / June and November / December
  • Annual – Every November / December

Commercial  organizations that succeed at applying feature updates at a rapid cadence have a preparation process that enables them to:

  • Assign an appropriate validation approach for critical and important applications
  • Select appropriate users, devices, and applications to form a pilot deployment group for the Windows 10 feature update
  • Effectively assess application or device incompatibilities and measure readiness for deployment against success metrics defined in the plan phase
  • Update supporting infrastructure, configuration, and security tooling
  • Notify users of upcoming changes to Windows and Office to take advantage of new capabilities
  • Configure and validate new processes and approaches as part of modernization initiatives

Recommendations on how to achieve the above outcomes are included below.

Compatibility preparation

With an application portfolio in place, and application importance/ownership assigned, critical and important applications can be tested. The focus of this section is how to test, what platform to test on, and how to expand testing to a pilot deployment group. Organizations that adopt a rapid approach test fewer applications than more cautious organizations, as they generally have confidence in their application and device compatibility.

Assign an appropriate validation approach for critical and important applications

  • Choose a validation approach for each application importance category – the types of compatibility tests performed should reflect the importance of the application to the business, to ensure any issues can be identified ahead of a broader deployment. One or more of the test approaches below should be defined for each application in the portfolio:
    • Regression testing provides full quality assurance and is performed by personnel familiar with the application
    • Smoke testing checks for install / launch failures, and is often performed by a resource with limited understanding of the application
    • Automated testing through tooling can test applications using the regression or smoke test approach and free up resources to perform other tasks
    • Testing during pilot deployment provides real world validation of applications and devices
    • Reactive response testing is typically performed during pilot and broader deployment, for applications with limited or no business impact.
  • Test on Windows Insider for Business builds to ensure there are no compatibility problems with critical applications – The Windows Insider Program for Business enables commercial  organizations to perform validation of applications ahead of the release of a Windows 10 feature update. This approach is recommended for critical applications with known compatibility issues to ensure any changes to Windows are identified early.

Select appropriate users, devices, and applications to form a pilot deployment group for the Windows 10 feature update

  • Identify users that can validate applications and provide feedback on new features / working scenarios for the next phase – having this mixture will ensure both functionality and usability of the platform will be tested in pilot deployment.

Effectively assess application or device incompatibilities and measure readiness for deployment against success metrics defined in the plan phase

  • Enable Diagnostic Data and use Desktop Analytics to automate the selection of critical / important apps on devices – If Microsoft Endpoint Configuration Manager is present in the customer environment, Desktop Analytics can be used to track application importance / ownership and use that data to automate the selection of devices to test for pilot deployment. This saves administrative time and effort to move to the deploy phase quicker.

Deployment preparation

Not all tooling and configuration that requires an update will be available before the Windows 10 feature update is released. Organizations that move at a rapid cadence update tooling and configuration when available, and document / triage issues that arise after a result of the update. They have shifted their approach from waiting until all tooling and configuration is available, to one where testing is part of daily use, and the production environment is constantly evolving as new updates are applied.

Update supporting infrastructure, configuration, and security tooling

  • Ensure infrastructure tooling is updated ahead of pilot deployment – ensuring infrastructure tooling is up to date ahead of the deploy phase enables an end to end test of the deployment process. For  organizations that use Configuration Manager, ensure the most recently release version of Configuration Manager is applied to the environment to support the new Windows 10 feature update.
  • Do not create, or delay the creation of a Windows 10 base image until after the pilot deployment is completed – Often,  organizations are stuck creating a Windows 10 base image early in the servicing process, delaying adoption of Windows by weeks or months. Windows Autopilot addresses many new and replace scenarios that a Windows 10 base image was created for. If there is a specific need for a customized Windows 10 image that can’t be addressed through the use of ‘vanilla’ OS media or through Windows Autopilot, ensure resource effort is not spent on creating an image until all applications, configuration and tooling is tested.

Capability preparation

Capability initiatives defined in the planning phase are implemented or configured in the prepare phase. The following recommendations can empower users to receive additional value out of Windows 10 and Microsoft 365 Apps:

Notify users of upcoming changes to Windows and Office to take advantage of new capabilities

  • Map new features / scenarios to workforce personas – Creating a draft of workforce personas, mapped to the edition of Windows and Office used in the environment, can create new ‘hero’ scenarios that showcase new or improved ways of working.
  • Provide communications to pilot users to showcase known new features / scenarios – Finding a communication strategy that is part of a broader change management approach helps users realize value from Windows will help reduce confusion about why updates will happen, and how they can be scheduled in a way that minimizes user disruption.

Modernization preparation

Modernization initiatives of the prepare phase can involve the following activities:

Configure and test new processes and approaches as part of modernization initiatives

  • Testing automation – some commercial  organizations utilize automated testing approaches for critical and important applications that enable them to standardize and accelerate validation of apps without the need for specialized resources.
  • Application transformation – Transformation projects that move critical applications from on-premises to the cloud reduce compatibility blockers and speed up adoption of Windows 10 feature updates.
  • Application consolidation – removing duplicate applications from the portfolio that perform the same purpose can reduce cost, supportability concerns, and testing effort.
  • Shifting to modern management – Moving to cloud infrastructure management tools removes the need to update tooling, and moving to update products such as Windows Update for Business places the responsibility for releasing updates to devices on Microsoft.  


Duration – Up to 12 weeks


  • Rapid – Every June, July, December, January
  • Annual – Every January-March

The method used to deploy a Windows 10 feature update depends on the tooling used. Deploying a Windows 10 feature update through Windows Update for Business has a unique shift from traditional methods. Specifically, rather than have “push” controls where IT sends down the update to the next ring using Configuration Manager, Windows Update for Business provides “pull” controls to stop the update that would automatically go to the next ring. This is a mental shift for many IT Admins, as they have little to do if everything is going right. More attention needs to be spent to determine if the update needs to be stopped or slowed in the event that end users have a poor or broken experience. Desktop Analytics provides real time data to help make decisions and increase IT confidence.

Commercial  organizations that succeed at deploying feature updates with no loss in business productivity and minimal user disruption perform the following actions:

  • They have flexible and agile deployment strategies per Windows 10 feature update release
  • They minimize bandwidth usage to reduce corporate network traffic
  • They have and meet success criteria to move to broad deployment
  • They monitor support cases and use data driven insights to troubleshoot or delay adoption if issues arise

These recommendations are expanded and split into pilot and broad deployment stages below:

Pilot deployment

Duration: 1-4 weeks

The pilot deployment begins when the prepare phase is complete with configuration and infrastructure updated. The first-time work to prepare and the results of the pilot provide long-term value for each future deployment by minimizing time to deploy of feature updates. Consider the following recommendations for pilot deployment:

Have and meet success criteria to move to broad deployment

  • Monitor the Windows 10 feature update to pilot devices – If a deployment of the feature update to an endpoint fails, Desktop Analytics can show where the deployment has failed or, if it is stuck, helping administrators isolate deployment problems quickly. If you are not able to use Desktop Analytics, review the log files and / or the SetupDiag tool to troubleshoot deployment with assistance from the remote worker.
  • Review and apply new configuration updates to pilot groups onlyAdministrative templates and Microsoft Security Baselines are available at the time of or shortly after the release of a Windows 10 feature update. New policy settings should be assessed and where possible, default settings should remain in place.
  • Use collaboration tools for pilot users to share their experiences – Effective end user feedback and escalation points are critical to any successful servicing model. Using tools such as Microsoft Teams can provide an effective way to capture compatibility challenges, and screen sharing can help users walk support or an operations teams through any issues experienced.
  • Leverage Windows 10 rollback functionality – By leveraging recovery options, users can return to productivity with the previous version of Windows if the user encounters an issue with the feature update. The ability to manually rollback reduces pressure on support and operations teams to triage issues, enabling them to investigate during scheduled work hours. The rollback process needs to be communicated well in advance for user convenience in case an issue is encountered, and the user needs to manually initiate the recovery.
  • Create a Frequently Asked Questions page – capture learnings from the pilot deployment to minimize calls to support during the deployment phase

Broad deployment

Duration: Up to 8 weeks

Once the pilot configuration is worked out to ensure a consistent predictable end user experience, and deployment rings created, broad deployment is ready to go. Configuration Manager provides granular controls to deploy Windows, and Windows Update for Business settings will continue to update devices unless the IT Admin purposefully stops deployment. The first time broad deployment is conducted, IT should monitor update velocity and consider increasing that speed for the next feature update.

Accelerate the deployment of Windows 10 by considering the following recommendations:

Outcome – Flexible and agile with deployment strategies per feature update release

  • Have a flexible approach to deployment – making one time assignments of devices to deployment rings leads to increased complexity when adopting Windows 10 at a rapid pace. Device compatibility may change per release, and what device assignment worked for one feature update might not work for all. Organizations that go quickly use tools such as Desktop Analytics to create deployment plans for production environments that are dynamic and based on compatibility testing results, which ensures devices that are not compatible at the time of deployment do not receive the update until the issue is resolved. This enables  organizations to deploy to their environment quicker and removes the need to pause deployment while discovered issues are addressed.
  • Enable users to schedule their installation or customize deploy times – Users of endpoints managed by Configuration Manager they can overcome disruption challenges by scheduling their own updates. Consider the use of a push pull model, where users pull down updates for a period of time before adding reminders and finally, forcing an installation. Note that this functionality is different in Windows Update for Business, which provides controls to deploy Windows during specified hours.
  • Use Autopilot to deploy new devices to remote workers Windows Autopilot leverages the OEM-optimized version of Windows 10 that is preinstalled on a new device. Instead of re-imaging the device, the existing Windows 10 installation can be transformed into a “business-ready” state, applying settings and policies, installing apps, and even changing the edition of Windows 10 being used (e.g. from Windows 10 Pro to Windows 10 Enterprise) to support advanced features.
  • (Optional) Create a reference image to support new and replace deployment scenarios – in scenarios where autopilot cannot be used, and there is a mandated requirement to ‘bake’ settings into an image, a reference image can be made once all supporting components and applications are tested and validated. However, it is strongly recommended that a custom reference image is not created, and the OS media or ‘vanilla image’ is used for these custom scenarios, with applications and configuration layered onto the device at deployment time.

Outcome – Monitor support cases and use data driven insights to troubleshoot or delay adoption if issues arise

  • Monitor increases for support requests – spikes in support requests after the deployment of a feature update should be aggregated and reviewed to ensure issues can be isolated and triaged accordingly.
  • Document any lessons learned and use them for continuous improvement – track deployment success, incorporate user and business feedback, understand reasons for delays, determine what worked well and what can be improved across efforts in compatibility, deployment, capability, and modernization. Use these lessons learned to document the time and effort spent servicing Windows as inputs to planning for the next Windows feature update, to focus on where improvements can be made to reduce time, resource effort, or cost.

Outcome – Minimize bandwidth usage to reduce corporate network traffic

  • Use delivery optimization tools for remote offices – not all locations in commercial customer environments are likely to be connected by high speed networks. Delivery Optimization is a peer-to-peer distribution method that can reduce bandwidth issues during updates by significantly reducing the amount of network traffic to Windows Update sources (Windows Update, Windows Update for Business, Windows Server Update Services) as well as the time it takes for clients to retrieve the updates.


This article has provided guidance and recommendations on how those organizations using on-premises tooling can fit Windows feature updates into regular work. By aligning to a plan, prepare, and deploy motion through the use of a calendar based approach, enterprises are able to maintain a serviced version of Windows 10 on a faster cadence, which helps to harden the operating system against malicious intent, simplify OS administration for IT, improve OS performance, add new capabilities, and unlock new working scenarios. As you repeat, refine, and modernize the process, the example timings stated in the article will reduce and the move towards a data driven servicing model will become easier. Examples of a successful transition can be found within our own Core Services Engineering and Operations (CSEO) team. Let us know if you find this article helpful, and what approaches work well with your company to stay current with Windows 10.

Brought to you by Dr. Ware, Microsoft Office 365 Silver Partner, Charleston SC.