The final countdown

With Windows 10, Microsoft announced that the days of ten-year support lifecycles were behind us thanks to this, their first evergreen operating system. We might all be better off for it, but if you’re still working with Windows 7, that fact will only hold so much comfort, as you still have one major deployment looming, and at this point, it’s looming large.

Microsoft has set January 14, 2020 – the ultimate Patch Tuesday – as the deadline day for upgrading from Windows 7 to Windows 10. After this date, Microsoft will put it into end of service, which means it will no longer provide support or security updates for users still on Windows 7, at least not without a price tag per device for extended support.

Part of the reason Microsoft ends support is to “encourage customers to move onto the next operating system”, according to Shirley Finnerty, Microsoft 365 business group lead.

“Technology is evolving all the time, and our core priority is to ensure customers have the highest level of security,” she said. “As each evolution of the operating system lands into the marketplace, there are new features that are particular to that operating system and can’t be replicated in the older versions, so our recommendation is for customers to move to the latest operating system as early as they can.”

The security piece is a huge selling point for those looking at upgrading to Windows 10. “The whole ethos around Windows 10 has been built on delivering the most secure platform and operating system for computers around the world. The key thing with Windows 10 is that security is built in rather than bolted on as an additional feature or solution that the customer has to purchase,” said Finnerty.

This version puts security to the forefront and has been designed to address issues in the modern workplace, where many employees now work remotely and take advantage of ‘bring your own device’ policies. This increases the complexity of protecting company data for IT managers, something that Finnerty believes is eased by Windows 10.

It has a whole host of security features, the highlights of which include Windows Hello, which allows companies eliminate passwords on their devices in favour of using biometrics for signing in; Windows Defender Exploit Guard, which scans for and removes malware, and in addition to providing ransomware protection, it includes tools which can be used to block quarantine programs on computers and isolate infected computers on a network; and finally, Windows 10 users can subscribe to Windows Advanced Threat Protection, which is effectively a solution that scans for malware and threats that have infected your infrastructure and will alert you as early as possible so you can remediate any threats in your environment.

“Some of the other benefits of Windows 10 bring feature updates, and some organisations are maybe okay to hold off without those in the short term,” said Finnerty. “But security is such a high risk, particularly at the moment when we’re seeing new attacks every single day. That would be our biggest concern for customers who don’t make that move.”

Depending on the size of your organisation, the number of employees and devices you have and the kinds of applications your business uses, the time it could take for your company to upgrade to Windows 10 could be anywhere between three months and 20 months, according to Martin Patterson, head of digital services at Auxilion, a Microsoft partner. This means the clock for upgrading may have been ticking for you for months now.

“Businesses have to have socialised this January 2020 date within their business and their budget,” Patterson said. “It’s about having an understanding of your IT estate and doing an assessment.

“I always say, let us do your homework, let us build your business case, let us give you a report that’s an enabler for you to walk into the financial officer or decision makers and say, ‘50 per cent of my machines won’t run Windows 10 and I need to buy 50 per cent of the business new hardware, and these applications won’t work so we need to look at that’. There are ways to arm yourself to go back to the people who control the purse strings to help a project move along.”

There is a five-step process for most businesses looking at upgrading, starting with a ‘readiness report’ that assesses how compatible your hardware and infrastructure is with Windows 10, resulting in a traffic light-coded measure of the state of your IT nation. “Everything is red, amber or green, indicating you need to complete this, remediate that or this is perfect. When you look at your report and everything is green, you’re golden and can move to the next stage, but if you have any ambers or reds, you’ll go into a remediation stage,” said Patterson.

The only thing holding you back from the deployment stage then is an application readiness assessment, which Finnerty believes is one of the big blockers for companies when they think about moving. “At the outset, it can appear to be quite a significant piece of work, but now with all the resources available to help customers through that process, it has become a lot more manageable,” she said.

According to Patterson, it doesn’t have to hold up the whole project for many businesses. “You can start with low-hanging fruit, start with the applications that work, and any applications we have challenges with or that need to be fixed or remediated, we can put them to the end of the project to give you a bit more time to actually do that,” he said.

While you won’t have to do a big-bang deployment ever again after Windows 10, it being an evergreen operating system does mean your final stage is a regular maintenance stage, something Patterson believes is the best thing for businesses.

“You have to maintain that image, you have to make sure that your platform is ready for the new update and any applications that need to be repackaged,” he said. “It’s not like Windows 7 where you do it seven years ago and then forget about it. This is going to be a constant cycle of keeping your image maintained, which is key as well, to keep up with your security obligations as a business.”

While implementation times vary by business, one thing Patterson believes is that as the countdown clock ticks, we’ll begin to see a crush later this year – something most businesses will want to get ahead of.

“What’s going to happen in the market is that there’s going to be a big push for a lot of businesses to get this done in the second and third quarter of this year and if they already haven’t started, they’re going to start finding it tight to get not just ourselves, but any other business or IT provider to get the project scheduled and delivered in the dates required.

“You’re going to see high demand for people to deliver these projects and there’s only a certain number of businesses in the country who can do it, so you want to be in front of it and not behind it to get it delivered on time,” he said.