By Massive IT · September 1, 2026
Microsoft publishes monthly updates to its cloud licensing and services. September 2026 brought several changes that affect how organizations run, secure, and pay for Microsoft. This summary covers what changed, who it affects, and what we recommend.
| Change | Effective | Who is affected | Action needed |
|---|---|---|---|
| Office, Project, and Visio LTSC 2021 reach end of support | October 13, 2026 | Organizations still running Office 2021 perpetual licenses | Plan the move to Microsoft 365 now |
| Microsoft Sentinel moves automatically to the Defender portal | September 2026, about 30 days' notice | Organizations using Microsoft Sentinel | Confirm your primary workspace and move rules and playbooks |
| One Copilot experience with agents and usage-based billing | Rolling out now | Copilot customers and anyone planning AI | Set a spending limit and cost controls before adopting |
| Extended Security Updates for Windows Server 2016 and Windows 10 LTSC 2021 | Available now | Older Windows Server and Windows 10 systems | Treat extended updates as a bridge and schedule the upgrade |
| Larger Microsoft 365 Copilot discounts for nonprofits | Through December 31, 2026 | Eligible nonprofit organizations | Ask us whether your organization qualifies |
1. Office 2021 perpetual licenses lose support on October 13
Support for Office LTSC 2021, Project LTSC 2021, and Visio LTSC 2021 ends on October 13, 2026. After that date these products stop receiving updates, security fixes, and technical support. Continuing to run them leaves you exposed to security vulnerabilities and compliance problems, because nothing new is patched.
Microsoft's recommended paths are straightforward:
- Enterprises: Microsoft 365 E3 is the primary path, with Office 365 E3 or Microsoft 365 Apps for enterprise as alternatives where they fit better.
- Organizations under 300 users: Microsoft 365 Business Premium, Business Standard, or Microsoft 365 Apps for business.
- Project and Visio: Planner and Project Plan 3, and Visio Plan 2, replace the 2021 editions and can be added on top of a Microsoft 365 suite.
Two details worth knowing before you choose. Microsoft 365 Copilot only runs on the cloud-backed apps included in Microsoft 365 suites, so a perpetual Office install cannot use it. And the Azure Information Protection labeling client for perpetual Office has been retired, so if you use sensitivity labels, moving to a cloud-backed suite is the supported route.
Our recommendation
- Tell us which machines still run Office 2021, Project 2021, or Visio 2021 and we will map the right upgrade for each group.
- Where a machine genuinely cannot move yet, budget for extended updates rather than running an unsupported product.
- Sequence the move by risk: internet-facing and regulated systems first.
2. Microsoft Sentinel moves automatically to the Defender portal
Starting in September 2026, Microsoft is moving customers who have not yet switched to the unified Microsoft Sentinel experience in the Microsoft Defender portal. Microsoft handles the scheduling and technical move, and tenant administrators see an in-portal banner and receive an admin email about 30 days before their onboarding date. Existing third-party connectors, content, and data stay in place.
The one thing to check is how many Sentinel workspaces you have. Microsoft selects a single primary workspace for Defender XDR alerts and incidents, and content that depends on XDR in a secondary workspace can stop working once that primary is chosen. Analytics rules, automation rules, playbooks, and workbooks that need to keep running should be moved to the primary workspace.
Related: the Microsoft Sentinel experience in the Azure portal retires on March 31, 2027.
Our recommendation
- If you use Sentinel, let us review your workspaces before the move and consolidate the rules, playbooks, and reports that matter.
- If you do not use Sentinel, no action is needed.
3. One Copilot experience, and a bill that follows usage
Microsoft has introduced a single Copilot experience that brings together three capabilities: Home, where chat and collaborative work sit alongside the full Office apps; Code, which lets non-developers build solutions; and Autopilot, a persistent, proactive, personal agent hosted in the cloud. New capabilities are arriving continuously rather than in one release.
The commercial model matters as much as the features. User subscriptions cover everyday use, while usage-based billing gives access to the advanced capabilities, and a new FinOps for AI layer is aimed at governing that spend and tying it to business outcomes.
Our recommendation
- Decide your monthly spending limit before enabling advanced Copilot capabilities, rather than accepting a default.
- Agree who reviews AI usage each month and who can raise a limit.
- Start with one pilot team and measure value before expanding to agent-driven work.
4. Extended Security Updates are a bridge, not a plan
Microsoft has made three years of Extended Security Updates available for Windows Server 2016 and for Windows 10 Enterprise LTSC 2021, with corrected pricing published in September. If you cannot upgrade those systems yet, extended updates keep security patches flowing.
They are a bridge, not a destination. Extended updates do not bring new features, and they cost money every year. Use the time they buy to schedule the upgrade rather than renewing indefinitely.
5. Better Copilot pricing for nonprofits
Through December 31, 2026, eligible nonprofit organizations can combine a Copilot promotion of 15% to 40% with the existing 15% nonprofit discount on Microsoft 365 Copilot. Previously it was one or the other. If you run a nonprofit that has been waiting on Copilot pricing, this is the window to ask about it.
Also worth knowing
- Microsoft Ignite runs November 17-20, 2026, in person and online, and the session catalog is open. If you would like a briefing on what is relevant to your environment afterwards, tell us and we will attend and summarize.
- Microsoft Dynamics 365 Activate is in limited public preview. It uses AI to assess an existing Salesforce environment and plan a move to Dynamics 365. If a CRM change is on your roadmap, this makes the assessment faster and cheaper than it used to be.
Next steps
If you are still on Office 2021, use Microsoft Sentinel, or are weighing Copilot, call us at (813) 518-5454 or email sales@massiveit.com and we will review what applies to your environment.
Source: Microsoft's September 2026 announcements. Details may change; Microsoft's terms govern eligibility and pricing.