M365 News Roundup for - May 2026
Why Copilot is Often the Default Choice for SMBs
A frequent point I make about M365 tools is that they might not always be the best of breed, but since you’ve already bought them to use Exchange, they are often good enough given the price point of a different tool.
Not always, but often.
That’s why this comparison of Claude and Microsoft’s Cowork agents made me chuckle:
Claude Cowork vs Copilot Cowork: why the Microsoft answer wins for SMB
Claude Cowork lives on your desktop. You mount a folder, drop your files in, and Claude runs in a sandbox on your machine. It doesn’t see your inbox. It doesn’t see your calendar. It doesn’t see your Teams chats unless you’ve copy-pasted them in. You bring the data to the model.
Copilot Cowork is the inverse. It already lives inside Microsoft 365, grounded in your Outlook, Teams, SharePoint, OneDrive, and calendar through Work IQ. You don’t mount anything. The model is already where your data lives.
I kind of agree, Copilot might not be the first choice of AI tools, but it is already connected to all your stuff, and the interactions live inside the tenant. That’s a lot when you’re trying to just do stuff with AI related to your work, which already lives in your tenant. Is it enough for every small-to-mid-sized business? I don’t know, but it will be enough for many of them.
Copilot News:
More info on Cowork - Copilot Cowork: From conversation to action across skills, integrations, and devices.
I haven’t seen this agent yet, but I’ll be interested to test it out when I do - Microsoft Legal Agent: Why Playbooks Beat Prompts for Real AI Workflows.
Speaking of agents - Microsoft Agent 365 Hits General Availability With Local AI Agent Controls.
More model choice - Available today: GPT-5.5 Instant in Microsoft 365 Copilot
An interesting question:
Finally, some learning material - Microsoft 365 Copilot app learning series: Real‑world scenarios for your workday.
Under the not entirely non-Copilot section:
If You Manage Entra Permissions, Watch This Before Deploying Agents
Operationalising Responsible AI: What Microsoft Purview Actually Enables and How to Use It Well
Non-Copilot News:
Is anyone going to miss this?
Together Mode for Teams Meetings to Retire in June 2026
This has been all over the news recently, and I’ve seen a number of them across our industry, too:
Cross‑tenant helpdesk impersonation to data exfiltration: A human-operated intrusion playbook.
Prepare yourselves.
I’m hopeful that this is as easy for users as Alerts were. We’ll see. - The New SharePoint Workflows Button.
Worth a read - Microsoft Purview Data Loss Prevention Diagnostics Explained
I cannot handle that they named this series of articles about updates to Defender and Security In the Loop, when there’s an actual product called Loop that is not related to this at all.
Please make it stop.
That’s all for this month’s roundup. What new stuff are you most excited about?