Windows 10 End of Life - Are SMB's Ready?

It has been a long time coming but finally, on October 14, 2025, Microsoft will officially end support for Windows 10. What does this mean for small and medium sized businesses (SMB's)?

SMB's can sometimes have difficulty updating systems when Microsoft's long runway for an operating system comes to an end.  Those that have been around for a while will remember the long drawn out Windows XP and Windows 7 end of life (We purposely left out the forgotten Windows 8). The good news is that Windows 10 computers will not stop working October 15th and beyond. However without security updates, running Windows 10 becomes risky, especially for SMB's. Options are to upgrade to Windows 11 or pay Microsoft for their Extended Security Updates (ESU) program, with the latter being very unlikely for SMB's.

Continuing to use Windows 10 pass October 14th may be necessary for several reasons. First, SMB's could be using legacy applications, like old accounting and ERP systems, which already lack support and can no longer be updated. This makes the prospect of updating to Windows 11 difficult if not impossible due to compatibility issues.  Second, SMB's may simply not have the current budget to acquire new hardware and software compatible with Windows 11.

As a company that develops accounting and ERP software for both macOS and Windows desktops, along with the cloud, we understand this update push from the many years of working with macOS. macOS is much quicker to push users/applications forward with new hardware and EOL (end of life) to older operating systems.

If you are a company that continues to use Windows 10, past October 14th, the following risks come with it:

1. Security Risks and Cyber Threats

No updates means no protection against new malware, ransomware, or phishing attacks. Hacker's love targeting unsupported operating systems because they know the flaws will never get fixed. For SMBs, one breach can mean lost data, downtime, and serious damage to customer trust.

2. Compliance and Legal Trouble

If you’re in a regulated industry, running an unsupported OS could cause failed audits, non-compliance fines, or even lost contracts. Cyber insurance providers may also raise rates—or deny coverage—if you’re still on Windows 10.

3. Rising Costs of Staying Behind

Sticking with Windows 10 may seem cheaper, but costs pile up fast: ESUs are expensive, software vendors will drop support, and IT teams will spend more time patching problems. In the long run, upgrading is less costly than dragging things out.

We are an SMB that uses the Connected Accounting and ERP application on Windows 10 - what should we do?

1) Update to Windows 11 and Connected 11.2. You need to be using the current version of Connected 11, because any version of Connected 10 or earlier were created when Windows 11 did not exist. This may be possible on existing hardware or new hardware may need to be purchased. Check out this article comparing Windows 11 to Windows 10  

2) Thinking outside the box, instead of updating to Windows 11, migrating to macOS may be an enticing option. With support for the Connected Accounting and ERP application, this is an option that can be considered.

3) Can't update to Windows 11 or change to macOS? Connected won't stop working but it will become more difficult to support. However, the biggest issues are those we have identified earlier - Security/Cyber Threats and Compliance/Legal Trouble

Can I avoid the risks of using Windows 10 by subscribing to the Connected on Demand cloud service?

Unfortunately, using our cloud service will not remove the risks of using Windows 10.  Again, the access and application will all work. However, the workstation used to access Connected on Demand will be still subject to the same risks as continuing to use the Connected Desktop application with Windows 10.

Can our business avoid the risks of using Windows 10 by subscribing to Microsoft's ESU program?  The short answer is yes for a temporary period of time.  This is just avoiding the inevitable. Additionally, as an SMB, this is adding costs that could be better used to upgrade vs maintain.  The costs get steeper each year, as outlined in the this KB article by Microsoft (https://learn.microsoft.com/en-us/windows/whats-new/extended-security-updates)

When being forced to update operating systems, nothing is comfortable, and it can be very disruptive for SMB's.  SMB's that use the Connected Accounting and ERP application have several options to move forward or stay put.  Our recommendation is to strongly consider updating to Windows 11 or macOS.  If Windows 10 is to be used after October 14th, without Microsofts costly ESU program, your business may want to consider removing these workstations from access to the Internet to avoid the potential threats.