This week in Microsoft, security, and AI: what changed and what it means for your business
Week of July 27, 2026 | A plain-English roundup for busy leaders.
Welcome to the first edition of This Week in Microsoft, Security, and AI. Each Monday, we will post a short read on the Covenant blog covering the changes worth knowing about so staying current is something you can do over coffee, not another chore you keep putting off.
Between Microsoft updates, new AI tools, and a steady drip of security headlines, there is more noise than any busy leader can track. Most of it does not matter to you. A few things genuinely do, especially when they affect your invoice, your help desk, your risk, or your next AI decision.
How to read this: no jargon, no scare tactics, and no attempt to turn every headline into a project. Just what changed, why it matters, and what to do next if it applies to your business.
This week’s quick list
Microsoft 365 prices went up on July 1.
If your bill looks higher, you are not imagining it. Microsoft commercial pricing changes are now in effect for select Microsoft 365 plans, including Business Basic and Business Standard. Existing customers remain on current pricing until renewal, which means the most important date is your own renewal date.
Exchange Server 2016 and 2019 are now firmly in migration territory.
If you still run your own email server, this is the one to circle. Microsoft says support for Exchange Server 2016 and 2019 ended on October 14, 2025, and organizations should be planning migration to Microsoft 365, Office 365, or Exchange Server Subscription Edition.
Sources: Microsoft Exchange end-of-support roadmap and BleepingComputer coverage of the ESU reminder.
Windows 10 is already out of standard support.
Windows 10 reached end of support on October 14, 2025. Extended Security Updates can provide a temporary bridge, but they do not include new features or general support. They are a planning tool, not a destination.
Source: Microsoft Windows 10 Extended Security Updates guidance.
The month’s Microsoft patches included flaws already under attack.
July’s Patch Tuesday was unusually large. Tenable reported that Microsoft addressed 569 CVEs, including three zero-days, two of which were exploited in the wild. The affected areas included SharePoint Server and Active Directory Federation Services.
Teams is now part of the phishing conversation.
Email is not the only place people are targeted. Microsoft Teams can also be used for spam, phishing, or impersonation attempts, especially when external chat settings and user verification habits are loose.
Source: Microsoft Teams guidance for external chat phishing and impersonation.
Thinking about Copilot? Get your files in order first.
A new survey reported that many organizations have delayed or cancelled Microsoft Copilot deployments because leaders are worried AI could expose confidential data, especially through old SharePoint sharing links and permissions that were never cleaned up.
Source: Infosecurity Magazine coverage of CoreView’s Microsoft 365 security research.
Your team is probably already using AI with company data.
Recent SMB-focused security commentary highlights the growth of Shadow AI: employees using public AI tools without IT approval. Often, the intent is good. People are trying to move faster. The risk is that company information can leave the business through tools no one is governing.
Source: TNGlobal: Shadow AI for SMBs.
Scammers are disguising malware as popular AI tools.
Attackers follow attention, and right now attention is on AI. Security researchers have reported malware campaigns disguised as popular AI services, including fake downloads that imitate tools people recognize.
Source: TNGlobal: Shadow AI for SMBs.
The bigger picture
Wouldn’t it be better if staying current on Microsoft, security, and AI did not mean doing the homework yourself every week? That is the whole point of this series. We watch the changes so you can spend your attention on the work only you can do.
If any of this raised a question for your business, the simplest next step is a clear baseline: what you own, what you use, what is exposed, and what should be handled before the next renewal, support deadline, or AI rollout.
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Explore FortifySources and further reading
- Microsoft 365 pricing and packaging updates
- Microsoft Exchange Server 2019 and 2016 end-of-support roadmap
- BleepingComputer: Microsoft to stop Exchange 2016 and 2019 security updates in October
- Microsoft Windows 10 Extended Security Updates guidance
- Tenable July 2026 Patch Tuesday analysis
- Microsoft Teams phishing and external chat guidance
- Infosecurity Magazine: Microsoft Copilot deployments delayed over security concerns
- TNGlobal: Shadow AI for SMBs
Want a second set of eyes on your Microsoft and AI readiness?
Book time with Covenant. We will help you understand what changed, what matters, and where to start.
