How to plan for Windows 10 Feature Update Deployment Remotely

If most of your employees are working from home, then upgrading them to the Windows 10 Feature Update is going to be a challenging task. Those computers won’t be around the IT staff physically to fix the problems. In this unique situation, you need a strategy that can help you deploy Windows 10 Updates smoothly.

Microsoft has offered a strategy that companies can follow to roll out the Windows 10 v2004 May 2004 Update. In fact, it can be followed for any feature update if the time demands.  Let’s take a look at the Microsoft’s suggested Plan for Windows 10 Feature Update Deployment Remotely.

Plan Windows 10 Feature Update Deployment Remotely

Laid out in three phases—Plan, Prepare, and Deploy—Business IT department can follow to deploy Windows Update securely through the internet.  It is rather obvious that one will have to use Configuration Manager or Windows Update for Business to complete this. The calendar below shows a potential timeline for rolling out Windows 10, version 2004, across the organization. Note that it is aligned with Microsoft 365 Apps and Configuration Manager release cycles.

Phase 1: Plan (June)

There are four parts of planning—Modernizing, Compatibility, Deployment, and Capability.

Modernizing should make sure Windows can be deployed securely, VPN configuration changes, Desktop Analytics, Co-management will be needed along with Windows Update for Business.  Followed by this is Compatibility planning where IT will have to make a list of applications used by remote workers, and figure out which of them are critical to be tested with feature update, and which will work just fine.

Next comes Deployment Planning, where the team has to be ready with all minimum requirements for deployment. That includes the latest version of Configuration Manager, InTune, and Windows Update for Business. You will also need to update Administrative templates, security baselines, and so on.

The last part of this phase is  Capability Planning, where everyone should know about the set of new features released with the latest update and should be able to find how to change it using Group Policy, Registry, and even PowerShell Commands.

Phase 2: Prepare (July/August)

It is divided into three preparation parts—Compatibility, Deployment, and Capability. All these are extensions to what was planned in the first Phase.

Starting with Compatibility preparation, it is advised to test all listed applications, especially those which are critical to work. The primary idea is to figure out how to test, and how to expand testing to a pilot group. That’s where the Desktop Analytics will give you insights and prepare for fixes and perform even more testing. There can be multiple approaches to testing, including the use of Desktop Analytics to create a pilot group of devices to validate apps and drivers.

Deployment Preparation is next to where the focus is need of infrastructure upgrade (if necessary), and configuration to support new Windows 10 Feature update and remote workers. It is highly recommended to pilot test to clearly understand how the process will take its shape when finally deployment starts. The steps to be followed are updating Configuration Manager, applying a new configuration to pilot devices, delay creation of Windows 10 base image, and then prepare for Windows Update for Business.

The last section in this phase is about Cabapility preparation. Here you can map new features to worker roles, and provide communications to pilot users to showcase known new features.

Phase 3:  Deploy (August/September)

There are only two phases here—Pilot and Broad Deployment. What is interesting here is the approach to deployment. It does not use any Red button to push updates down to all devices—instead, its a pull approach to preventing the update from automatically going to the next ring.

The Pilot phase is recommended to start in August, where based on the prepared configuration and infrastructure from the Preparation Phase. Using Windows Update for Business, updates are sent out in the smallest update package size, and lowest latency. That is why the VPN configuration was necessary, and a more cloud-based approach was suggested instead of locking those computers to the corporate network.

Pilot Phase is critical, and it is recommended to monitor the pilot devices closely by taking feedback, data from the analytics tool. If things go south, Windows 10 Rollback can be used immediately.

The last part is where you go ahead for Broad Deployment, depending on how successful the pilot deployment. You can use deployment rings, and Windows Update for Business will continue to push updates. To accelerate deployment, Microsoft recommends to expand configuration and policies, enforce compliance deadline for the update, create broad deployment plans, keep a tab on support requests, creation of baseline image, autopilot to deploy new devices to remote works, and document the experience.

Rollout out Windows 10 Feature update is a different ballgame for Businesses. There are a lot of factors that need to be taken care of and carefully planned to make sure there is no massive breakdown. It is essential that IT admins document everything, so it helps the next time one has to do it again.

Make sure to go through the official website for more details on this process.