How to Ensure a Smooth Windows 11 Migration for Your Enterprise

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How to Ensure a Smooth Windows 11 Migration for Your Enterprise

Whether you’re upgrading your enterprise to Windows 11 or updating to the latest version of Windows10 (hint: Windows 10 1909 is EOL in May 2022), it can be a daunting prospect. Without proper planning and implementation, you risk impeding user access or halting business operations which can cost your enterprise millions of dollars.

To show how you can reduce the risk, time, and effort of your Windows servicing program, we’ve created a step-by-step guide. Along the way we’ll show you how this can be orchestrated and automated using the ReadyWorks Windows servicing module integrated with the Access IT Automation Access CAPTURE platform.


Step 1: Collect Asset Information

To begin your Windows migration, you first need to understand your project scope. Pulling together an inventory of your users, devices and applications and understanding dependencies means accessing and aggregating data from multiple systems and spreadsheets.

ReadyWorks connects to all your COTS and homegrown Systems Management and Access Management Systems, CMDBs, as well as all other relevant tools and repositories, allowing you to quickly unlock the potential of ‘dark data’ held across systems.

Step 2: Rationalize Data & Analyze Risk

Before you can build your migration plan, you’ll need to rationalize all data, identify missing information, and analyze application, hardware, and user readiness to reduce program risk.

Depending on the size of your organization it can take months to complete if done manually. The longer these activities take, the more changes will happen across the company, introducing greater risk as your project information becomes outdated.

ReadyWorks uses AI to clean and normalize critical program data and then uses this data to analyze application, hardware, and user readiness. In doing so ReadyWorks reduces program risk and eliminates the thousands of hours spent manually rationalizing data.


Step 3: Identify Incompatible or EOL Hardware

By coordinating hardware refresh activities with your Windows servicing program you can reduce the number of systems you need to update by approximately 1/3 (based on average 3-year lease cycles). Windows 11 has more stringent hardware requirements, so you’ll also need to replace or update machines that do not meet these requirements ahead of rollout. If your enterprise lease cycles are longer than three years you may want to revisit as Windows 11 is fully supported only on PCs sold in 2019 and later.

ReadyWorks identifies hardware compatibility with Windows 11 requirements. You’ll be able to see:

  • What’s nearing EOL or incompatible with the new OS and needs replacing.
  • Which machines need to be upgraded, including those that need a memory upgrade or BIOS update to be compatible with Windows 11.

Step 4: Automate Hardware Upgrade Workflows

ReadyWorks allows you to bridge the gaps created by these disparate tools to automate at scale and manage Windows servicing alongside the hardware refresh activities that often fall through the cracks.

Hardware Replacement

As hardware is identified for replacement, emails are triggered to end users and managers to notify them of the change and ask them to confirm their hardware requirements via the ReadyWorks self-service portal. Endpoint teams are then automatically assigned tasks relevant to the hardware refresh requirements.

Once engineers mark a new build as ready, an end user receives an email, notifying them of next steps and asking them to use the self-service portal to confirm their address and select a shipping date. Once all data is entered, a notification is sent to the IT engineer so they can ship equipment.

They can leverage pre-defined and custom templates to automate communications with end users, providing information such as tracking number, how to set up their machines, where to get additional help, and how to return old equipment. There’s no need to spend time chasing old equipment via email, as ReadyWorks automatically sends reminders asking for equipment to be returned if it’s not been done by a particular date.

Hardware Updates

If your project data identifies hardware that needs to be updated ahead of the Windows upgrade, you can leverage ReadyWorks automation to manage those workflows too. ReadyWorks allows you to:

  • Trigger automated communications to users explaining the reason for the upgrade and what is required of them, for example in terms of how to get the hardware to IT to update.
  • Automate scheduling via self-service capabilities.
Categorize and Test Apps

Step 5: Categorize and Test Apps

Your next step is to review and test your applications to understand compatibility with the new OS. You don’t want to crash your VP’s access or halt mission-critical operations, but you also can’t afford to spend nearly a year testing all your applications.

Using ReadyWorks in conjunction with Access IT Automation, you don’t have to. We advise that you streamline testing to about 15% of your estate and you can do that by tiering your apps:

Tier 1: Mission-critical apps.

These will likely be approximately 10% of your estate and are the apps used to run essential business operations or accessed by VIPs. These need to be formally pre-tested and certified to mitigate risk of business disruption.

Tier 2: Important applications.

These apps are used by high volumes of people but not mission critical. We advise running software pilots, managed within ReadyWorks, to test these and only roll them out to the wider organization when you get feedback that everything is ok.

Tier 3: : Low risk COTS or home-grown apps.

These are used by small groups of people. They can be rolled out without waiting for feedback, halting rollout only if issues are found.

Using ReadyWorks and Access IT Automation you can streamline the process of grouping and testing applications ahead of rollout.


With a list of applications aggregated at the data discovery phase, you can identify mission-critical applications and mark them as Tier 1 within the ReadyWorks dashboard.

ReadyWorks uses AI and machine learning to make intelligent decisions about which applications should be Tier 2 and Tier 3 based on information such as numbers of users or user types. You can control this by adjusting the number of users per app that define the tiers, and by manually updating the tier in the dashboard.

You can then risk score your apps to determine the number of software pilots you need to complete before rolling them out to the wider organization. ReadyWorks provides a risk score and defines the number of pilots that need to be managed. You can change scores or criteria within the dashboard at any time.

Automate Your App Tracking and Testing

Managing the application and testing process leveraging the capabilities of Access IT Automation’s Access Capture platform, you’ll also be able to cut your packaging and testing workload by around 50%.

Access Capture has been helping enterprises around the globe automate the otherwise labor-intensive, lengthy, and expensive processes, of application packaging and testing, giving them 360-degree visibility into their application estate and helping instantly achieve the scalability and agility required to achieve their goal of utilizing modern applications.

Access Capture provides a clear dashboard of the applications you have identified for pre-testing and uses intelligent workflows, both to minimize the amount of work involved, and to allow non-technical product owners to test and package their own apps. Using Access Capture, you can spin up pools of virtual machines running the latest Windows 11 build within seconds and install existing apps, inviting the appropriate product owners to test as part of the workflow. You can also track and manage the application re-certification process. This enables you to minimize any possible business disruption caused by older applications that do not function in this new environment.

With Tier 1 applications formally certified against the OS, readiness criteria are then automatically updated within ReadyWorks via an ETL connection with Access Capture.

Managing Software Pilots

With a clear view of all your users, and systems that use your tier 2 apps, you can begin defining your software pilots. ReadyWorks suggests computers that fit the criteria, and by selecting friendly users that have been helpful in the past, you can automate a pilot wave workflow. The workflow includes automated email communications to notify them of the pilot program, confirm the user’s willingness to participate, and explain what is required of them.

Once pilot waves have been deployed, users are asked to confirm that the rollout has been issue-free or report any glitches within the self-service portal. If there are no issues within a defined timeline, applications are automatically marked as ready, meaning they are compatible with Windows 11.

If there are issues, applications will be moved into a new group, identifying that they need further investigation and ensuring the update cannot be rolled out to machines that leverage those applications until issues are resolved.

Automate Scheduling and Deployment

Step 6: Automate Scheduling & Deployment

Scheduling deployment rings manually quickly eats up IT resources as you go back and forth with users to understand blackout days, critical working hours, team priorities and, finally the individual’s availability. Leveraging automated communications and the self-service portal within ReadyWorks you can cut the time and effort of these activities.

ReadyWorks allows you to automate communications and survey teams to understand the business requirements so that when it comes to scheduling individuals you already have a head start. Once deployment rings are identified, a notification is sent to each user within that ring to allow them to schedule a time that works for them within that window based on your team’s availability – this means cutting the time you spend on scheduling activities.

If anything changes, users can update their requested time slot. Automated reminders are sent as the scheduling date draws near. When it’s reached, ReadyWorks will automatically add those users to the SCCM ring.

If issues do occur with applications during rollout, you can mark this within ReadyWorks, ensuring that you won’t be able to select machines using those applications for future rollouts until the issue has been rectified. This means you only spend time manually managing the small proportion of issues that can arise, rather than your entire estate.


Step 7: Automate Reporting

As Windows updates are rolled out your project data is automatically updated in ReadyWorks. Rather than spending half a day pulling together that information manually into a PowerPoint or Excel file, you can simply send your project stakeholders links to reports within the ReadyWorks dashboard for them to view at any time.

Lessons Learned

There’s a common misconception outside of IT that managing Windows updates is simple. We know that’s not true, but by using ReadyWorks and Access IT Automation you can take the time, hassle, and risk out of all your future Windows Servicing programs.

Schedule a demo to learn more.


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