Beyond Migration: How to Overcome Windows 10 Update Challenges

With just a few months remaining for Windows 7 support, companies around the world are scrambling to get their machines up to date before the January 14, 2020 deadline. For those with a large number of devices and remote employees, it’s been an extremely long and arduous process, and many still have a long way to go.

Are you one of them? In fact, 56% of companies feel their Windows 10 migration isn’t happening fast enoughOpens a new window . It comes as no surprise then that, on average, just 68% of machines have been migrated, with retail, public sector, media, construction and financial services the farthest behind. Despite recognizing the security advantages—82% say security is a motivating factor—there’s still a great deal of work to be done.

For the vast majority, remote work seems to be the biggest issue. With so many devices “out in the wild,” 77% of organizations say it’s just extremely difficult to even reach those machines, let alone keep them up to date and secure. Making matters worse, these remote devices are arguably some of the most vulnerable. Unlike on-premise workers who at least have some perimeter protection inside the firewall, remote workers routinely tap into public Wi-Fi at the local coffee shop or the airport, which increases the risk of compromise.

Even those who’ve crossed the finish line with Windows 10 migration may be disappointed to find that the race is far from over. While its major bi-annual build upgrades and routine bi-weekly smaller updates certainly add to the enhanced security, they can also be a disaster for IT teams who may find themselves in a “Groundhog Day” mini-migration nightmare scenario every six months.

The problem with Windows 10 maintenance after the migration is twofold:

1. Companies lack visibility into their current software estate. Organizations have visibility over just 64% of their total software estate on average, leaving a huge blind spot of 36%. This makes it next to impossible to know what’s already installed on devices and how these applications might interact with—or interfere with—regular Windows 10 updates.
2. Many organizations don’t have control over endpoints. Across every business sector, IT admits having access to and administrative control over fewer than 60% of endpoints on average—only 52% in the financial services and construction industries. This makes it extremely hard to keep up with updates and permissions, especially on remote devices.

Because of this lack of visibly and control, organizations say only 2/3 of the software estate (including OS, patches, device drivers, etc.) is current today. Without some way to resolve this problem, it will only get worse in the future, as Windows 10 updates start to roll in. And, that could leave organizations just as vulnerable as before the migration. Even the most secure OS in the world can’t do its job to protect endpoints if updates and patches aren’t applied.

So, what must organizations do to prepare for and deal with ongoing Windows 10 maintenance?

1. Complete the migration. If you haven’t done so, get it done. Not only is it critical to have the most modern, robust and secure OS running on all of your endpoints, it also helps tremendously to manage all of the devices when you’ve standardized on the same OS. Having a mishmash of machines all on various systems is a nightmare to keep up with. Getting every device on the same level playing field gives you a fighting chance.
2. Rope in remote devices. In many cases, remote workers are on their own, free to maintain or not maintain their machines, and even to install software of their choosing. This can be extremely problematic, introducing rogue applications that may have access to your network or your data. Establish firm policies that forbid users from declining, delaying or ignoring OS updates and from installing unauthorized software without proper IT authorization.
3. Deploy centralized Windows servicing solutions. Gain visibility into every machine by deploying device management platforms that give IT access to every endpoint on the network—even remote ones. These purpose-built Windows servicing solutions augment tools built-in to the OS, giving IT the ability to query any machine, see its current software status, gather system data for troubleshooting and perform other tasks vital to the health of the machine and your organization’s security.
4. Automate OS update deployment and installation. If you thought it was tough to keep endpoints up to date now, it’s going to be nearly impossible with Windows 10, unless you bring in an automated solution. These tools give IT the flexibility and power to manage updates efficiently without overtaxing resources. For example, with automation, IT can queue up large updates and push them to machines during off-hours when bandwidth is more readily available, and it won’t disrupt users’ productivity. The most advanced automation tools can even reach remote machines with limited connectivity and “on time,” and pause and restart updates to account for bandwidth and power availability.

As the deadline for migration draws closer, many organizations are coming to the dreaded realization that migration was only half the battle—maintaining Windows 10 is an equally foreboding challenge.

But with the right approach, the right policies and more flexible, modern, purpose-built tools on your side, Windows 10 can deliver the features, security and device standardization your organization needs, without an overwhelming, never-ending hassle.