Windows Servicing: Best Practices and Resources

Windows Servicing

Planning a Windows update? Follow these best practices to reduce the time, cost, and risk of your program.

Moving to Annual Windows Servicing

When Microsoft released Windows 10, it sparked a change in the way Windows Servicing programs are managed. With updates issued semiannually and support for new versions limited to 30 months, it is no longer possible to run these programs every 5-6 years and take 2 years to complete them. To maintain security and ensure users have access to the latest features, you'll need a new approach for managing the ongoing cadence of updates.

Addressing the Challenges of Windows Servicing

By increasing the frequency of updates, Microsoft wanted to simplify the rollout process and provide a consistent user experience with a single operating system for all devices. But no IT infrastructure manager would describe a Windows update program as simple. With a more complex environment, greater workloads, and end users more widely distributed in the wake of the COVID-19 pandemic, even more challenges have arisen.

To help address the challenges – both old and new - we’ve put together a comprehensive list of tools and approaches that IT managers can adopt to alleviate pressure and remove the risks associated with Windows Servicing. We’ve also identified some growing opportunities for service providers.

“IT organizations waste an average of $101 million for every $1 billion spent on projects and programs due to poor project performance.”

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Windows-as-a-Service (WaaS)

In a world where technology evolves at a rapid pace, the introduction of Windows-as-a-Service (WaaS) with Windows 10 meant we no longer had to wait years for new features. Microsoft now issues two types of updates:

Feature updates are delivered twice per year
– in the spring and fall.

Quality updates are delivered monthly and
include both security and non-security fixes.

These are made available via the following channels:

Insider preview allows early adopters to access updates as they are developed and provide feedback to Microsoft on compatibility with existing features and any issues they encounter.

Servicing Channels allow enterprises to decide when to deploy features:

The Semi-Annual channel receives feature updates twice per year.
The Long-Term Servicing Channel is used for specialized devices that have new feature releases every 2-3 years, such as ATMs.

Deploying Windows Updates

The goal for any Windows update is to make sure that the new features and patches don’t adversely affect the tens of thousands of end users, applications, business operations or devices within an enterprise. Microsoft suggests using ‘deployment rings’ or waves to pilot updates with less critical users in the earlier waves, allowing you to correct any issues before deploying to VIPs and other prominent personnel. For industries with a high number of business-critical users, including financial, pharmaceutical, manufacturing, and healthcare, it’s clear that isn’t going to work.

Before you start to deploy, you have to consider the following:

What applications are used in the organization and how are they accessed?

Which applications need to be tested?

What hardware is nearing end-of-life or won’t work with the new OS?

How will the schedule be structured?

How will you handle logistics?

What tools do you need to access?

To do this at scale, you’ll need to adopt some level of automation.

Windows Servicing Tools

There are several Windows deployment tools available to help facilitate your rollout:

Systems Management tools (BigFix, SCCM, InTune), to gain data about hardware and installed applications.
CMDBs to add more granular details about ownership & entitlements.
Access Management Systems (AD, Okta) to identify applications that aren’t installed locally.
You may also be pulling in network information to pinpoint location.
HR Systems to help you identify managers and escalations paths.
Asset management records to identify software and hardware lifecycles.

These tools will probably get you the information you need, but not in real-time or aggregated into a single view. Traditionally this is done by project managers using spreadsheets, and Post-it notes - and this where the errors, delays, and cost overruns start. By the time the data is collected and aggregated, changes to the business mean it’s already out of date. It’s clear you’re going to have to take other factors into consideration before you can begin your program.

To automate Windows Servicing, you need a command and control system that collects and manages information in real time.

Best Practices for Windows Servicing

To reduce the risk of impacting user access or business operations during the update you should:

DECIDE WHICH APPLICATIONS NEED TO BE TESTED Clearly you can’t afford to devote up to 9 months to pre-testing, but you don’t want to blindly roll out the update for fear of crashing access to critical applications. To protect your rollouts, we recommend sorting applications into three levels and adopting new testing strategies, including software pilots, to cut the number of applications you pre-test to around 15% and reduce validation time by months.

COORDINATE WINDOWS UPDATES WITH HARDWARE REFRESH CYCLES Identify which equipment has reached EOL, is incompatible with the new OS, or is due for replacement. Use automation to streamline the logistics of coordinating hardware refreshes with Windows updates.

LEVERAGE A SELF-SERVICE PORTAL TO SCHEDULE USER UPDATES Automatic reboots aren’t well received during customer meetings or when they take out the CEO’s access. If you don’t want to risk this, you need to understand business priorities, blackout dates, and critical working times as well as which users need to be scheduled together and who can give the ok on timing. Remember to factor in a longer time to update remote workers. Use self-scheduling to reduce the risk, cost, and time for Windows 10 Servicing.

AUTOMATE COMMUNICATIONS, SCHEDULING, DEPLOYMENT, AND REPORTING Communicating with users and managers to understand scheduling needs, scheduling, rolling out and rolling back the update, and reporting all take multiple team members many hours of work. Automate these tasks to reduce repetitive tasks.

CONSIDER HOW YOU'LL DEPLOY UPDATES TO REMOTE WORKERS As we’ve already noted, with a more distributed workforce, you’ll need to devote even more time to Windows 10 Servicing programs. Here are 5 tips to help you overcome the new challenges of rolling out updates to remote workers.

"ReadyWorks saved our team at least 1 year of work for a project manager during our Windows migration project – particularly in organizing, managing, and automating the application certification process – and delivered a far better end user experience than previous projects."

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Leveraging the deployment tools already discussed, it’s clear you are still going to have to devote time and budget to continue managing Windows 10 enterprise updates manually.

How to Achieve Hassle-free Windows Servicing

If you want to remove the risk of overrunning your budget and the hassle of manually managing Windows Servicing programs, you have a few options:

Spend: Make Windows Servicing a full-time role or outsource these programs every year.

Build: Custom build a platform in-house by analyzing your tasks and workflows. This is possible, but do you have the time and money to devote to this or to maintain it every year?

Adopt: To really automate Windows servicing, you can adopt a ready-built command and control platform – one which can be customized to all your needs and which will orchestrate your existing tools to collate data in real time and automate workflows – to take the time and hassle out of Windows servicing, as well as many other IT infrastructure programs.

To do this at scale, you’ll need to adopt some level of automation.

Windows Servicing Automation

By automating repetitive chores, you can automate over 50% of your Windows Servicing program. Automate:

Data analysis and collection
Planning
Communications
Scheduling users

Deployment
Rollbacks
Reporting

Download the ReadyWorks eBook: Your Ticket to Faster, Risk-Free, Windows Lifecycle Management

Revenue Opportunities for Service Providers

IT spending is ‘expected to grow by 4% to over one trillion U.S. dollars worldwide’ in 2021, and automation taking on a greater role in service delivery. This means a growing number of opportunities for managed service provides who adopt automation for their Windows Servicing programs.

Using automation to manage repetitive tasks at each stage of your customer’s Window servicing project, you can:

Complete pre-sales activities quickly and easily and provide more accurate customer quotes.
Cut the headcount required to manage the program, increasing profit margins and revenue, and allowing you to serve more customers.
Leverage an agile approach to react quickly to customer needs.
Reduce issues and keep projects on track for a positive customer experience and to improve customer retention.

Gartner sees ‘asset-based consultancy’ – a category of managed services that includes a prebuilt system targeted at a specific multicustomer problem with a multiyear contractual service to deliver business outcomes – as becoming increasingly popular.

It expects that by 2025 more than 69% of service providers will leverage asset-based consultancy solutions for over half of their portfolio. Find out what you need to do to act early and take advantage of this growing market.