The leaves are changing, Halloween decorations are multiplying, and somewhere an office thermostat has officially started its annual war between “why is it 78 degrees in here” and “who turned the heat off?”

October also happens to be a pretty important month in technology history. On October 29, 1969, researchers sent the first message over ARPANET, the precursor to the modern internet. They were trying to send “LOGIN”, but the system crashed after just the first two letters “LO.”

So, the internet basically began with an outage. Fifty-seven years later, we’ve gone from ARPANET struggling to send two letters to AI writing emails, creating software, and occasionally making us wonder whether any of us will still have jobs by the next newsletter.

Let’s dive into October’s updates!

Eight episodes, countless cloud security concepts, and more four-letter acronyms than we ever want to remember.

Our final episode in our Demystifying CSPM series looks at where CSP is headed next, including its evolution into CNAPP and how capabilities like CWPP, CIEM, CASB, and XDR come together to give you a more complete view of cloud risk. We also dig into connecting seemingly isolated security findings into an attack story, automation, integration, and what a mature cloud security program looks like going forward.

Come for the cloud security. Stay because you’ve invested too much time learning these acronyms to quit now.

Watch the final episode and complete your journey through the CSPM alphabet soup!

Apparently even virtual machines eventually start thinking about retirement.

Microsoft has put more of its older Azure VM families on the path toward their golden years, including Dv3/Dsv3 and Ev3/Esv3, which are scheduled to retire on November 14, 2029.

But Microsoft would prefer you not wait until the retirement party. Beginning February 1, 2027, pricing is also changing for several older v1 and v2 VM series, along with VM and Storage pricing in select Azure regions.

Consider it Microsoft’s increasingly subtle way of saying, “Have you thought about modernizing?”

If your Azure environment has been happily running the same VM families since nobody can quite remember when, now is a good time to take inventory. Your VMs may still have some working years left in them, but their retirement planning just became a budget conversation too.

Remember when Copilot was the new intern who helped summarize meetings and write emails? Apparently, it has career aspirations.

Microsoft is rolling out the next evolution of Copilot with Home, Code, Cowork and Autopilot.

In other words, we’re quickly moving from “Copilot, help me do this” to “Copilot, go do this.”

Of course, greater responsibility usually comes with compensation. Microsoft says Cowork, Code, Autopilot, and other long-running agentic capabilities use usage-based billing, so your AI workforce may not demand health insurance, but it has figured out expense reports.

… don’t even get me started on the new personal agent being named Autopilot, cause that doesn’t overlap something entirely different from Microsoft.

Read Microsoft’s announcement

We already had one retirement above with Azure VMs. Last month we had the Windows 10 ESU year-1 retirement notice. And now November is brining even more.

Anybody else noticing a theme as we approach the end of the year?

On November 10, Windows 11 Enterprise and Education 23H2, Windows 11 IoT Enterprise 23H2, .NET 8 LTS, PowerShell 7.4 LTS, and Azure IoT Edge 1.5 LTS all reach end of servicing. The Azure Functions .NET in-process model reaches the end of support that day as well.

Apparently, Microsoft is doing some year-end housekeeping, and your environment may be on the chore list.

Take inventory now, make your upgrade plans, and please just us next month when we presumably announce that Clippy has finally decided to cash in his 401(k).

See Microsoft’s list of farewells in 2026 here.

Remember last month when we confidently told you Copilot Business usage-based billing was coming in November?

Yeah… about that….

Microsoft has moved the rollout to December 1, 2026. So, technically we weren’t wrong, we were just briefly correct.

Starting in December, new Copilot Business licenses obtained through CSP will have usage-based billing enabled by default. If Copilot Business is something you are considering, mark your calendar for this change… but make sure to use pencil 😉.

It’s almost that time of year again. Microsoft Ignite returns November 17-20, which means four days of announcements, demos, new features, new names for things you just learned the old names for, and at least a few moments where everyone collectively asks, “Wait… is that included in my license?”

This year, expect AI and Copilot to be front and center, with a particularly heavy focus on AI agents and what it takes to actually govern and secure them. Microsoft is also putting plenty of attention on cloud and AI platforms, security, data, business applications, and Windows.

The important part isn’t keeping track of every shiny new feature announced on stage, it’s figuring out which announcements will actually affect your employees, security posture, licensing, and technology roadmap.

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!