You want to keep running Windows 7? Good luck with that, small businesses

The end of Windows 7 support is days away. Microsoft says small businesses can pay for extended security updates just like their enterprise cousins. My experience says it's challenging to find help, but it's out there if you know where to look.

For small businesses that need Windows 7, it’s time to ask for help

[This post was originally published in December 2019. It was significantly updated and republished January 6, 2020, with contact information for CSPs that can help small businesses acquire ESU licenses.]  

Support for Windows 7 ends in just a few days. After Jan. 14, 2020, Microsoft will no longer provide free security updates and bug fixes for the venerable operating system to the general public.

Those updates will be available, however, to Microsoft customers who are willing to pay for the privilege. The Windows 7 Extended Security Update (ESU) program runs for an additional three years, through January 2023, and it's been officially available since Dec. 2, 2019.

When Microsoft first announced the Windows 7 ESU program, in September 2018, the company said these updates would be available to its most valuable customers: Giant corporations and government agencies with volume licensing subscriptions and medium-sized businesses and educational institutions with Windows 10 Enterprise or Education subscriptions.

Then, in October 2019, Microsoft extended the program to businesses of all sizes. If you run a small business (even a sole proprietorship) and you want to keep using Windows 7, that should be good news. But as I learned this week, Microsoft doesn't seem particularly interested in taking your money if your business is too small.

Anyone who administers Windows PCs in a large organization with an active volume licensing contract has it easy. They can deploy ESU to Windows 7 devices by downloading a Multiple Activation Key (MAK) from the Volume Licensing Service Center and then installing a few servicing stack updates and using a command-line tool to register the new key.

Businesses that aren't big enough for a volume licensing contract, however, are not so lucky: Microsoft says you small fry have to purchase Windows 7 ESUs through one of its partners in the Cloud Solution Provider (CSP) program. Sounds easy, right?

It's not.

In December 2019, a month before the end-of-support date, I went in search of Windows 7 ESUs, figuring it would be a simple task and I could share the step-by-step procedure here. I discovered that unless you already have a relationship with a friendly CSP, the process is far more difficult than it should be.

My starting point was the same one Microsoft expects you to use if you're interested in the ESU option, the comprehensive, official Microsoft FAQ about Extended Security Updates for Windows 7. There, you'll find this Q&A:

Who should I contact for more information about pricing and ordering for Windows 7 ESU?

VL customers: Please contact your Account Team CE for pricing and ordering information that is tailored to specific customer scenarios.

Customers who are interested in purchasing Windows 7 ESU in CSP should reach out to a CSP partner. You can find a qualified partner at this site.

That link takes you to the Microsoft Solution Providers database. I filled in the three blanks, specifying my business location (US) and size (one to nine employees). But the final field, which asks for "products, services, skills, industries, or organizations," is a stumper. I settled on "Cloud Solution Provider," which returned eight results.

After reviewing the capsule description for each provider, I wasn't encouraged. All the recommended firms were large consultancies with broad-based skillsets, targeting companies that will pay them big bucks to do medium- and large-scale deployment and development tasks. None of them seemed like the type of firm that would be interested in a onesy-twosy license deal with a very small business.

I chose the maximum of three providers, entered a description of what I was looking for, provided contact information, and clicked the Send button.

Within 15 minutes, I had a response. Unfortunately, it wasn't exactly what I was hoping. The No. 1 provider on my list, the one Microsoft had assured me, was the best match for my request, was "unavailable."

Twelve hours later, I got another message, apologizing that my second-best match was also "unavailable."

A day later, I got an encouraging notice that my request had been accepted by the third partner. They had my contact information, but nearly three weeks later, no one from that firm has followed up with me. For those keeping score, that's three strikes.

Meanwhile, I contacted the two companies with whom I already have an established reseller relationship and asked if they could help. Both are CSPs, but neither one was willing or able to assist. One said, "Sorry, no." The other seemed stumped but passed the request along to someone who might have more detailed product knowledge. A few hours later, I got this reply:

Unfortunately, you would need to reach out to a reseller to purchase this license. We're not able to sell to an end user directly.

Another reseller that I contacted confirmed that scenario exactly, replying to my request with this note:

Hello,

We received your message regarding Windows 7.

We are Cloud Solution Provider and only provide licenses for customers who have a commercial account.

If you are interested in becoming a commercial customer of Microsoft please let us know. 

A reader who works in IT support for a well-known educational institution contacted me to share his experience. He used Microsoft's contact form, just as I did, and was able to find only one partner willing to help, but that partner required a minimum order of 25 licenses, at a cost of more than $1500, just to begin a conversation. 

That's an awful lot of hoops to jump through to buy a single product key that's good for a year and doesn't require any deployment or support. What's especially galling is that Microsoft long ago allowed customers to skip all those partner hoops and buy Office 365, Microsoft 365, and other cloud-based services directly from the Office 365 portal.

I suppose I could keep trying, but I'm not feeling optimistic; instead, I'm disappointed that Microsoft has chosen to make this option so difficult. I've worked with Microsoft's cloud partners before, and it's not a simple point-click-pay-activate process. Instead, you have to set up an Azure Active Directory tenant, create a reseller relationship with a partner to give them access to your Azure AD portal, and then have them fill your order.

Also: The PC was supposed to die a decade ago. Instead, this happened

It's almost like Microsoft wants people to become discouraged and give up.

It doesn't have to be this way. Microsoft has been serving pop-up notifications about the Windows 7 end-of-support deadline for several months now. After support officially expires on Jan. 14, 2020, Microsoft is going to start delivering a full-screen warning to PCs that are still running Windows 7.

You would think that any of these pop-ups would be an ideal opportunity to help diehard Windows 7 fans access those paid updates. Just add one more option: "Pay for extended security updates." Give people the usual dire warnings about how it's a dead-end and Windows 10 is more secure. Make them click through an ironclad legal waiver. Hell, require that they upload a video of themselves holding today's newspaper to prove they're serious. But if they want those updates, Microsoft, take their money.

Update, January 6, 2020: After publishing the original version of this article, I heard from two Cloud Solution Providers that focus on small businesses and said they're willing to assist, even though this is a money-losing proposition for them.

Alex Stanton, Managing Partner of Exbabylon IT Solutions, noted that Microsoft didn't provide details of this program, including pricing, to its CSP partners until December 1st, the day before it went live to the public, and there's "no incentive for CSPs to promote this because it won't be a moneymaker for them."

Stanton says that the companies who need ESUs the most are those with 50+ employees who have specialized equipment like a CNC milling machine or a medical device that they can't afford to unplug. "If a customer is not a good fit, we will find a good fit for them," he told me. But, he continued, "We want to hear that customer say, 'We are working with the [equipment] vendor on upgrade options. There's a valid business reason for this.'"

I also heard from Amy Babinchak, President of Harbor Computer Services, a CSP that specializes in "giving small businesses access to quality IT services." If you're a small business looking for an ESU license, you can provide your contact details via this online form. Babinchak notes that her firm is willing to help small businesses but can't provide services for other IT firms. "We are not making money from these transactions," she told me. "I'm considering it simply a community activity and the right thing to do."

Finally, Dave Joss of DGJ Network Solutions reached out to say "We are a Microsoft CSP and will be happy to get these licenses for small businesses." You can contact the firm at (469) 675-0989.

if you're the owner of a CSP and you're willing to help out small businesses who are looking for ESU licenses, hit the contact form (the email icon next to my by-line at the top of this article) and send me a message and I will add you to this list.