Microsoft Customer Update - September

Microsoft has announced a series of updates across Windows, Microsoft 365 Copilot, Cloud Solution Provider licensing, Windows 365 and Azure Reservations. While some are small changes, others could have a bigger impact on how organisations plan migrations, renewals, AI adoption and cloud costs over the coming months.

Windows 10 reached end of support on 14 October 2025, but for many organisations the move to Windows 11 is still a live project. It is not just about replacing an operating system. It can affect security, user experience, device strategy, budget planning and wider digital transformation priorities. Remaining Windows 10 devices should now be reviewed against upgrade readiness, refresh requirements, Extended Security Update needs and whether Windows 365 could offer a practical route to Windows 11 for users who cannot move directly to a new physical device.

Read more: Windows 10 reaching end of support - Microsoft Lifecycle | Microsoft Learn

For customers, the useful starting point is understanding what each remaining device is used for and what the best route forward looks like. Some devices may be ready for Windows 11, some may need replacing, some may be better suited to Cloud PC delivery, and others may need ESU as a short-term bridge while a longer-term plan is completed.

• Identify any remaining Windows 10 devices and confirm whether they can move to Windows 11.

• Review device refresh plans, including where Copilot+ PCs could support performance, security and AI-readiness goals.

• Consider Windows 365 for users or scenarios where cloud-based Windows access is a better fit than immediate hardware replacement.

• Use ESU only as a temporary option while a supported long-term plan is completed.

Taking the time to map this out can help reduce risk, avoid rushed decisions and create a clearer path to a supported, more modern Windows environment.

From 1 October 2026, Microsoft is applying a 5% cost of capital uplift to annual-term Cloud Solution Provider software subscriptions that are billed monthly. This affects software subscriptions such as SQL Server, Windows Server, Client Access Licences and System Centre where customers have committed to an annual term but chosen to spread payments monthly.

This is not a blanket increase across all CSP subscriptions, so customers do not need to assume every agreement will be affected in the same way. Annual billing is not changing, and month-to-month subscriptions are not affected in the same way. The practical impact will depend on how agreements are structured, when renewals fall, and whether monthly billing is still the right choice once the uplift is applied.

For finance and procurement teams, this creates a useful moment to review options before renewal. Some organisations may still prefer the predictability of monthly payments, while others may find annual billing gives them a better total cost position, particularly across larger software estates.

A quick billing review now could help customers make more informed decisions before the change comes into effect.

Extended Security Updates for Windows Server 2012 and 2012 R2 end on 13 October 2026. Windows Server 2016 then reaches end of support on 11 January 2027, creating another important milestone for organisations running older infrastructure.

These dates matter because server modernisation is rarely quick. Older platforms are often connected to legacy applications, dependencies, vendor constraints and wider operational processes. By starting early, organisations can build a clearer view of affected servers, understand workload ownership, assess migration or upgrade routes, and decide whether ESU is needed as a temporary measure.

Planning ahead can help avoid last-minute pressure and make sure older infrastructure is addressed in a way that supports both continuity and longer-term modernisation.

Microsoft is renaming the Windows 365 Frontline family of service plans to Windows 365 Flex from 3 September 2026. This is a branding update rather than a licensing or functionality change, but customers may need to update internal documentation, reports or service desk references once the new name appears.

Read more: Windows 365 Flex | Windows 365

Microsoft has also introduced new Cloud PC configurations for Windows 365 Enterprise and Flex. These include two new 32 vCPU sizes with 128 GB of RAM and either 1 TB or 2 TB of storage, alongside a new GPU option called Select for multimedia-optimised applications. Windows 365 Flex also now supports GPU-enabled Cloud PCs in Shared Mode. Read more: What's new in Windows 365 Enterprise | Microsoft Learn

For customers, this continued development of Windows 365 gives more options when thinking about secure access, hybrid working, specialist users and device refresh planning.

Microsoft continues to release new Copilot capabilities across Microsoft 365, including stronger integration with business systems and third-party data sources, enhanced meeting preparation and summarisation, new Planner Agent features, AI-generated status reports, more advanced SharePoint and OneNote experiences, and improved connector performance for faster access to organisational content.

Read more: Release Notes for Microsoft 365 Copilot | Microsoft Learn

For organisations already using Copilot, the opportunity is to move beyond early adoption and focus on where it can make work easier day to day. That could include reducing manual reporting, improving meeting follow-up, accelerating content creation, supporting knowledge discovery or helping teams work more consistently across Microsoft 365 apps.

Microsoft has also made Microsoft 365 Business Standard with Copilot and Business Premium with Copilot permanent offerings for SMB customers rather than limited promotions. This makes Copilot easier for smaller organisations to adopt without separate licensing complexity.

Read more: New Microsoft 365 Business with Copilot SKUs available July 1

From 18 August 2026, Microsoft is also simplifying the Copilot experience with updated app branding, clearer separation between work and personal accounts, and URL changes from m365.cloud.microsoft to copilot.cloud.microsoft.

Read more: Updates to Copilot and the Microsoft Copilot app | Microsoft Support

As Copilot becomes a more established part of Microsoft 365, it is worth regularly reviewing new capabilities, governance needs and priority use cases so teams can get more value from the tools they already use.

Microsoft has confirmed that from 1 February 2027, Reservations purchased for any service supported by one of the Azure Savings Plans will no longer be eligible to be exchanged. Existing Reservations can be exchanged one more time after 1 February 2027, but the change reduces future flexibility for customers using Reservations as part of their Azure cost management strategy.

Read more: Changes to the Azure reservation exchange policy - Microsoft Cost Management | Microsoft Learn

For workloads that may change, move or scale in different ways, Azure Savings Plans may offer a more flexible alternative to traditional Reservations. Reviewing this ahead of the 2027 deadline can help customers make choices that better match their future cloud strategy.

For customers using Reservations as part of their Azure cost optimisation approach, now is a good time to sense-check reservation coverage, workload stability and future architecture plans before making new commitments.

Keeping on top of Microsoft updates can be time-consuming, especially when licensing, security, infrastructure and user experience decisions all overlap. boxxe can help you understand what these changes mean for your organisation and where you may need to take action.

Whether you are planning a Windows 11 migration, reviewing CSP billing options, assessing older server estates, shaping your Copilot adoption plan or looking again at Azure cost optimisation, our team can help you build a practical route forward that supports your people, priorities and budget.