The kids are back in school, football is back on TV, and AI is threatening to end humanity on Earth. September has become the season of digital productivity where every platform seems determined to introduce a new assistant, agent, or automation feature. Fortunately, we’re keeping score so you don’t have to.

Let’s dive into our September updates!

All good things must come to an end. But don’t worry, we’re not yet there with our CSPM webinar series. 😁😁

In our newest episode, we tackle CSPM maturity and pitfalls. We’re looking at what separates simply having CSPM tolls from actually having a mature CSPM program by knowing what you have, understanding what matters, prioritizing real risks, automating responsibly, and making sure somebody actually owns the problem.

We’ll also dig into some of CSPM’s greatest hits with alert overloading and treating compliance like a synonym for security. Check out our latest episode and learn to turn a mountain of security findings into something your team can actually do something about.

Better yet, subscribe and don’t miss new episodes on all upcoming series!

Beginning October 1, Microsoft is adding a 5% increase to annual-term, monthly-billed CSP software subscriptions. Before you start profanity-ridden rant to your computer screen, this is NOT a blanket price increase across M365.

In typical Microsoft fashion, their terminology in “software subscription” is completely different than what the rest of us immediately think it means. So, unless you see Microsoft saying there is an increase for “per-user license-based Online services,” M365 and all those other productivity services are not changing.

In this case, Microsoft’s “software subscription” means Modern Software via CSP, which means subscription-based licenses for things like Windows Server, SQL Server, and those other on-prem sounding products that are acquired through the CSP channel. This doesn’t mean that you shouldn’t worry but rather check what Modern Software subscriptions you may have as at their next renewal date post October 1 as you will be seeing an increase then.

Read the official announcement CSP Software Pricing Update Effective October 1, 2026.

Starting November 2, 2026, Microsoft will automatically enable usage-based billing for all new Microsoft 365 Copilot Business subscriptions. That sounds like a small administrative change, but for customer’s it’s actually a big shift.

Think of it this way. Up until now, buying Copilot was like buying an unlimited gym membership. Starting in November, Microsoft is also handing you a smoothie tab and saying, “Don’t worry, we’ll just bill you for whatever extra stuff you use.”

The good news is that customers can immediately take advantage of newer AI capabilities such as Copilot Cowork and Work IQ APIs without having to jump through several setup hoops first. That’s great for accelerating adoption and getting value from AI faster, but terrible if you don’t prepare for employee spending sprees.

There will be some guardrails in place, such as a default $10 per account, per month spending plan as well, but that $10 adds up fast when you have hundreds of employees.

Doesn’t seem like Microsoft is really announcing this directly to end customers, but you can read more from the Microsoft CSP Partner blog here.

Remember when Windows 10 support ended last year and we said, “We’ll just buy Extended Security Updates for a year while we finish moving to Windows 11?” How’s that going so far?

Year 1 of the ESU is up, ending on October 13, 2026 (regardless of when you actually bought it). It was supposed to be a stopgap to give companies a little more time to migrate without leaving Windows 10 devices exposed, but Microsoft actually calls the ESU a last resort and temporary bridge to a supported platform.

Well, if that migration is still going on, you can buy Year 2, but Microsoft doubles the price each consecutive year. At some point, “we need a little more time” cannot turn into “Windows 10 ESU is our retirement home” as there is no Year 4.

AI adoption doesn’t happen all at once. There’s a big difference between experimenting with AI and confidently putting it to work across your business.

We’re developing a new AI service built around our AI adoption model designed to help you move through that journey. Our focus will be getting you from using AI as a glorified Google search to managing AI agentic output that actually produces results for you.

The goal isn’t simply to give you more AI. It’s to help your business become ready for what AI makes possible.

More coming soon. The agents can wait. Your AI strategy probably shouldn’t.

Our monthly checkpoints are your all-access pass to asking all the cloud questions you may have. Whether that is bouncing new ideas off of, looking for guidance on specific solutions, learning more about upcoming capabilities, diving deeper into a technical issue, or simply just being your monthly emotional support human. If you don’t have a monthly team checkpoint already scheduled, don’t be shy, drop us a message and let’s get one scheduled!