Blog Archives - Chicago IT Support & Cyber Security

The AI Free Ride Is Starting to End

May 22, 2026 by Edward Silha

The AI subsidy era is ending, and the bills are finally showing up.

Microsoft is reportedly cutting back internal Claude Code licenses and steering developers toward GitHub Copilot CLI instead. It matters because this is Microsoft, not some cash-strapped startup. This is the company that poured billions into OpenAI, owns GitHub, and runs one of the biggest cloud businesses on earth. If even Microsoft is looking at token-based usage and deciding the math does not work, everyone else should probably pay attention. [Read more…]

Hackers Are Now Using Microsoft Teams to Break Into Corporate Networks

May 14, 2026 by Edward Silha

For years, companies drilled one thing into employees’ heads: don’t trust weird emails. Problem is, attackers adapted. Instead of fighting against people’s skepticism around email, they moved to platforms employees already trust without thinking twice about it. One of the biggest targets right now is Microsoft Teams

A threat group called KongTuke has been using Teams chats to get inside corporate networks, and honestly, it’s working disturbingly well. Instead of blasting out phishing emails, they pose as internal IT staff and message employees directly through Teams. Sometimes they’re operating from already-compromised Microsoft 365 accounts. Other times they create fake accounts designed to look close enough to pass a quick glance. Either way, the attack can go from first contact to compromised system in just a few minutes. [Read more…]

AI is increasing the intensity of work rather than reducing it

April 8, 2026 by Edward Silha

There’s a growing argument that AI is increasing the intensity of work instead of reducing it, and honestly, that tracks.

Everyone keeps talking about how AI is supposed to save time. That’s technically true. The problem is what happens next.

You finish something in half the time, and instead of getting breathing room, you get more work. Not later. Immediately. What used to be a full day turns into half a day, and now you’re expected to fill the rest. That’s what people are actually feeling right now. It’s not less work. It’s the same job compressed and then expanded again. [Read more…]

Microsoft Eliminates SharePoint Email Passcodes, Forcing Move to Entra Guest Accounts

March 13, 2026 by Edward Silha

Microsoft is retiring the email passcode system long used to grant temporary access to shared files in SharePoint Online and OneDrive for Business. The company plans to replace it with Microsoft Entra B2B guest accounts, shifting external collaboration toward a fully identity-based model across Microsoft 365.

The change affects both commercial and government cloud environments. Beginning in May 2026, new external sharing invitations will start using Entra B2B instead of the existing one-time passcode system. The transition will accelerate through the summer, with the older authentication method beginning its shutdown in July and disappearing completely by the end of August 2026. [Read more…]

Microsoft Adds Passkey Sign-Ins to Windows, Expanding Phishing-Resistant Authentication

March 11, 2026 by Edward Silha

Microsoft is expanding passwordless security across Windows by introducing passkey authentication through Microsoft Entra. The new capability allows users to sign in to Entra-protected resources using Windows Hello instead of traditional passwords, adding stronger resistance against phishing attacks and credential theft.

The feature will roll out as an opt-in public preview starting in mid-March 2026 and continuing through late April for global Microsoft 365 tenants. Government cloud environments will receive the preview shortly after, with deployments scheduled between mid-April and mid-May. Once enabled, the update allows organizations to adopt passkeys as an authentication method on Windows devices. [Read more…]

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