The news
Microsoft (MSFT) is pushing three separate deadlines onto corporate IT teams this fall. The price of keeping Windows 10 patched is doubling, Exchange Web Services is being switched off in Exchange Online, and a Windows 11 update changes a default setting for managed devices.
The biggest cost item is Windows 10 Extended Security Updates (ESU), the paid program that keeps delivering security fixes after Windows 10 reached end of support on October 14, 2025. According to The Register, commercial customers paid $61 per device for the first year, which ends in October 2026. The second year costs $122 per device and the third, and last, year costs $244. Windows 365 users are exempt from ESU costs, the outlet reported.
Many companies are still running the old system. Statcounter data cited by The Register put Windows 11 at 71.5% of Windows desktop usage and Windows 10 at 27.77%. Esben Dochy, principal technology evangelist at asset-management firm Lansweeper, told The Register that the doubled second-year price makes the business case for replacing lingering machines "a lot easier."
The second deadline affects software integrations. Exchange Web Services (EWS) is an older programming interface that lets apps read and write mailboxes, calendars and contacts. The Register reported that on October 1, 2026, Microsoft began disabling EWS in Exchange Online tenants in phases, and that the service will be permanently retired on April 1, 2027, with no exceptions. On-premises Exchange Server is not affected. Admins can temporarily re-enable EWS and allow specific apps, but only until the April date.
Microsoft is steering developers to Microsoft Graph, its newer API, though the company has acknowledged that some capability gaps remain, The Register reported. Microsoft said EWS no longer meets today's security, scale and reliability requirements, according to the outlet.
The third change is smaller but touches policy. BleepingComputer reported that after the release of Windows 11 version 26H2 on September 29, 2026, Windows settings backup is enabled by default for devices that are Microsoft Entra-joined or Entra hybrid-joined. The default applies only where admins have not configured the policy, and excludes regions covered by the EU Digital Markets Act and sovereign or restricted clouds. Restore stays off unless admins turn it on.
The numbers
- Windows 10 ESU, year 1
- $61 per device
- Windows 10 ESU, year 2
- $122 per device
- Windows 10 ESU, year 3
- $244 per device
- Windows 10 share (Statcounter)
- 27.77%
- EWS final retirement
- April 1, 2027
Why CEOs should care
For CFOs, the ESU math is now simple to run. A company with 1,000 Windows 10 machines would pay $122,000 for year two and $244,000 for year three at the list prices The Register reported (our calculation). Compare that against the cost of replacing or upgrading those devices, and ask IT for a dated plan to retire each remaining Windows 10 machine rather than renewing by default.
For CIOs and application owners, EWS is the deadline most likely to cause surprises. The Register noted that organizations may first learn of forgotten integrations through failed workflows and help-desk tickets. Ask vendors of CRM, archiving, scheduling and backup tools whether they still call EWS, and get written Graph migration dates. Because Microsoft says some Graph gaps remain, test the specific mailbox and calendar functions your business relies on before the April 1, 2027 cutoff.
For CISOs and compliance teams, the settings backup default is a policy question, not a crisis. If your organization has not set the policy, Windows 11 26H2 devices will start backing up settings automatically. Decide whether that matches your data-handling rules, and set the policy explicitly in Intune or Group Policy so the outcome is a choice rather than a default.
The bigger picture
Taken together, the changes show Microsoft using pricing and hard cutoffs to move customers off older platforms. The doubling ESU schedule raises the cost of waiting each year, and the EWS retirement, announced in 2023 after feature development stopped in 2018, ends a decades-old interface that dates back to Exchange Server 2007, according to The Register.
Lansweeper's Dochy told The Register that the steepest part of the Windows 11 migration curve is likely behind the market, which suggests the remaining Windows 10 fleets are the hardest cases: specialized machines, older hardware and teams that have deferred the work.
What’s next
Watch for the end of the first ESU year in October 2026, when renewals at $122 per device come due, and for Microsoft's phased EWS blocking across tenants ahead of the April 1, 2027 retirement. Organizations that re-enable EWS temporarily should treat that as a short bridge, not a fix.
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