“Looking Out on the Morning Rain,” I See More Tumult and Change Coming

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All IT providers, from the Systems Administrators at Fortune 500 companies to Managed Services Providers (like me) who help small business owners, have a competing set of objectives. One is to satisfy the technological and business requirements of their clients. The other is to work within the constraints (sometimes edicts) of the vendors they use to provide and build those business solutions.

The most significant “elephant in the room” is inevitably Microsoft. Just when everyone took time over the recent year-end holidays to relax after the massive effort to migrate from Windows 10 to 11, the calendar page flipped to 2026, and the meme associated with the phrase, “objects in mirror are closer than they appear,” took on new meaning.

Microsoft identifies dates well in advance for the end of support (or end of life, EOL). In the coming year, several significant events are scheduled for October. The first is that Office 2021 will reach EOL. This stalwart is the one-time installation software that has been available as a long-term license (rather than subscription). It has been superseded by Office 2024.

And within the Office family, Microsoft has also issued a death knell for Publisher. This product is no longer available in the Office 2024 edition, and Microsoft will remove it from all Office 365 subscriptions (in which it still exists) in October 2026. I hate that decision because I create all of my client-facing documents in Publisher, including this newsletter. There are very few alternatives I need to investigate (and learn), but more on that next month.

Also, in October, Microsoft will end support for Windows 11 version 24H2. I will ensure that all clients running this version of the operating system receive the recently released 25H2 update in late August or early September to maintain support and security (including monthly updates).

The subsequent entry on a longer-term calendar is the January 2027 end-of-life for Windows Server 2016. What I learned from a recent event (Windows Server 2012 went EOL in October 2023) is that many organizations — more than I ever expected — held on to ancient hardware for as long as possible, even if it slowed down their entire operations.

I understand trying to wring the last vestige of usefulness out of a hardware device that initially cost thousands of dollars. But the cost was amortized, and the device was fully paid off long ago. And yet, when it comes time now to replace a Windows Server 2016 with a new server, with the rapidly rising price of memory (RAM), business owners are going to be shocked out of their chaise by the prices of new Windows Servers.

While I do not like churn (of either hardware or software) for its own sake, in most cases, new hardware performs significantly better than older hardware — even if the old hardware has not broken. Similarly, newer software — despite the incessant push to include AI — offers features and benefits for anyone interested in taking advantage of them.

If all you use is a web browser to read your email and go to websites, you can use your phone. But if you have a line-of-business application that is still server-based, you will need new hardware. Dell is pricing its Windows Servers at astronomical prices, and things are going wild!

In a recent Reddit post, another MSP stated that on Wednesday, their Dell representative could not honor a Monday quote for a pre-configured server. He was questioning the community to see if this is “real or Memorex.”

The first response came from someone in the industry, who said, “I quoted [a] customer yesterday about 900 USD per 64GB RAM stick. Today, new pricing came in… 1600 USD per stick. Our quotes are valid for a day, it’s so crazy atm” [atm means “at the moment”].

Can you imagine seeing a nearly 80% price increase in something within one or two days? That is the current — and rather unfortunate — state of the world.

Having said that, I am thrilled that I was able to upgrade more than 95% of my clients’ computers to Windows 11 machines last year. Those who must upgrade this year — due to age or lack of warranty — I’m warning you now, you will pay significantly more.

What Not to Do When You Have a Data Breach

Sax LLP (“Sax”), also known as Sax Advisory Group, disclosed a 2024 data breach in December 2025 that affected its systems. Yes, more than a year and a half after the “unusual network activity” in August 2024, the firm notified almost a quarter of a million individuals that their information was exposed. Compromised information included name, date of birth, Social Security number, driver’s license information, and passport number.

I don’t think anyone affected is feeling very good about this. If I were a victim, I’d be screaming to the heavens about why it took so long between identifying the breach and notifying those affected — especially given the range of information that was exfiltrated. This breach is an awful case where identity theft could run rampant for these victims.

Thanks, and safe computing!

Microsoft Ignite – All About Agentic AI for Windows

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Microsoft Ignite is the annual partner conference that the Redmond-based software company hosts. The mid-November 2025 conference exceeded 20,000 attendees, while estimates are that more than 10 times that many registered for online sessions (including yours truly). This event focused on demonstrating how Microsoft is implementing AI and its cloud platforms now.

The central theme with respect to Windows was Microsoft’s push towards an “Agentic OS,” in which it would gradually integrate AI agents into the taskbar and OS for proactive assistance.

Let me take a step back from all that geeky jargon and explain some things. First and foremost, OS stands for operating system – and that is all Windows is: an OS. Other operating systems include Linux and Google Chrome (on specifically built devices). AI stands for artificial intelligence. In this instance, it is the code Microsoft links to for specific questions and answers (basically the rules by which things should happen), based on their LLM (large language model) and a ton of code. Agentic is a trickier word. Most often, it refers to systems that can plan multi-step actions and adapt to changing circumstances independently. The simplest way to explain this is to remember the ESP-like qualities of Radar O’Reilly in the old MAS*H TV episodes, where he would automatically know – and state out loud – what his commander wanted done before it was even uttered.

Let’s put these various fragments together so they make some sense. Having an “agentic OS” means that Windows would know what you want to do and either help you or do it for you. I’ve worked with technology for a very long time, and I’m a child of the 1950s. Let’s go back 30 years (using the WABAC Machine – a Rocky and Bullwinkle reference) to recall that Microsoft gave us Office 97 and Clippy, a verbose (frequently maligned) assistant to help us work with Word and Excel. No one liked it!

Well, now, Microsoft plans to have a Copilot for Windows that will help you navigate settings and Windows updates and attempt to solve problems (some of which you might not even realize you have) to “fix” or “optimize” your computer.

Look, this is all really terrific, and quite frankly amazing, stuff. But most of what Microsoft is building is geared toward business users in large enterprises. When it comes to small- to medium-sized businesses and consumers, they’re implementing this stuff, and it is going to confuse the heck out of the “end users.” After an initial outcry, Microsoft agreed that it would not automatically turn on this AI support tool and would let it be up to the computer’s owner to say, “Yes, I want to let Microsoft know even more about how I use my computer, what files I have on it, who I communicate with over email, and what websites I visit.”

Ah, yes, the privacy issues. If you have an active AI agent running 24/7 on your computer as you do whatever it is you do, looking at all those activities, you’d have to be incredibly naïve to believe that you still retain your privacy. Microsoft will tell you they won’t use the data they are scooping up by the petabytes, but that’s not at all reassuring. I’m still waiting to see all the settings I must turn OFF to ensure client safety in future Windows releases.

Thanks, and safe computing!

Microsoft Is All-In on AI

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I had the opportunity to attend Microsoft’s annual partner conference, Ignite, in mid-November. Microsoft held this event in Chicago’s McCormick Place. According to the trade press, more than 200,000 people attended, of which 14,000 were there in person.

The primary topic at most sessions revolved around artificial intelligence (AI) and Microsoft’s version called Copilot. And in true Redmond fashion, there are copilots for almost everything.

Outlook will have a version that can read through all your emails, view the tasks on your calendar, and learn about your contacts. It will allow you to prioritize which emails you should respond to. In some of the more expensive versions, Microsoft 365 (what used to be known as Office) will have Copilot read through your Word documents, Excel spreadsheets, and PowerPoint presentations to summarize information about a client or business prospect.

Of course, to do this, all your files must reside in Microsoft’s OneDrive cloud environment (not in your Documents folder). Eventually, Copilot will be “smart enough” to read through SharePoint libraries, the equivalent of commonly used document folders. Teams will have a Copilot, allowing you to schedule meetings with your colleagues. It will listen to each speaker and take notes. At the end of the meeting, it will summarize the session for all the participants and send them out.

What is left unspoken is that all these activities require considerable effort from the company that wants to deploy Copilot to engage in data governance. This phrase means deciding who can access what data and when among countless rules and settings. Well, guess what? Microsoft has another product, called Purview, that assists with this effort. Large organizations will hire consultants to take on this challenge. I have a few ideas about what smaller companies will do, but most cannot take on the monumental task – that often takes months of meetings – to set the appropriate rules in place. And that means the likelihood of data exfiltration and users who might access information they would not usually be able to. The net result could be an increased risk of a data breach.

The Large Language Model (LLM) that forms the basis of Copilot is still undergoing rigorous testing to ensure it holds no racist or misogynistic tendencies. Microsoft insists it will not use YOUR data to help build up the model because of privacy rules. Of course, I believe that implicitly. No, I have my doubts.

But here’s the thing. While Copilot can summarize information from disparate sources and help “knowledge workers” (remember that awkward phrase?) speed up mundane tasks, I suspect how things will eventually work out. Everything sent through this AI engine is going to sound plain and soulless. For example: Both John and Mary report to Janice. All of their documents are in OneDrive and SharePoint. Janice asked each one to summarize some information from a recent set of meetings. Now, Microsoft says that sometime next year, John and Mary can collaborate using Copilot to build the resulting work effort for Janice. My questions are: How useful will the presentation be? Will it contain sufficient information for decision-making, or will it be full of the verbal fluff common to business writing?

The implications of using AI for business are fascinating and other-worldly stuff. I was mesmerized by the carefully crafted live presentations of this technology. There were moments when I had to laugh about how intrusive the AI was. Still, I realized Microsoft has this event to evangelize its products and ensure partners sell more products to small, medium, and enterprise businesses.

Oh, and if you want Copilot for Microsoft 365, it will cost $30 per month in addition to your existing Microsoft 365 subscription. I don’t think many of my small business clients will distribute this to all their staff. Yet, I believe a few savvy business owners will invest in this technology to see if it can speed up some manual processes or streamline putting together quotes and proposals.

Thanks, and safe computing!

End of Year Musings About How Things Might Change

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We are coming up to the end of 2023. During the past year, only one product has been released in the computing environment that I think will change our future: ChatGPT, the artificial intelligence (AI) bot released by OpenAI. It is now in its fourth iteration from its original release in November of 2022. Yes, you can prank ChatGPT by asking repetitive questions. Yes, it still has hallucinations and will give incorrect answers. Yes, you are only now getting recent data in responses (rather than the outdated original data set). And yet, people are using it in myriad ways.

Microsoft has already spent $13 billion to provide OpenAI with the resources needed to build the product. I believe that amount will likely double in the next two years. Satya Nadella, CEO of Microsoft, is “all in” on AI because he knows the more you and I use bots to help us operate our computers, the fewer people will be required to do more work. If someone can document a process and then have the AI read all the documentation associated with a topic (e.g., how to fix the problem when your computer can’t print on your wireless printer), then you don’t need a human being at a call center in India or the Philippines.

You can have a computer user open a Windows 11 CoPilot application, type their question, and engage in a question-and-answer session. The cloud-based software will walk that person through all the known steps to fix the problem. Am I worried about my job because of this? No, because despite the computer-provided hand-holding, sometimes you need a human being who has experienced “real world” problems to ask questions no one asked the AI bot. As I have seen in many demonstrations, when ChatGPT doesn’t know an answer, it cannot even say, “I don’t know,” so it provides incorrect or misleading information. That is a significant problem that still consumes the minds of the data scientists who build these models. And it is why I think we are far from having AI “take over” things.

In the same way, businesses will create AI-based products for more and more fields. Do you need an insurance quote? Of course, the preliminary questions and responses you receive will be from an AI bot. You’ve all seen the silly commercials for “Limu Emu and Doug.” After all, Liberty Mutual extols the virtues of customizing insurance so “you only pay for what you need.” How do you think they are going to handle that soon? It is simple: they will develop an AI bot to work with you. For instance, you’re a young married couple in Livingston, NJ. You own an $875,000 house with 25 years on your mortgage. You have two kids (ages 9 and 6) and lease a Tesla Model 3 and a Toyota RAV 4. Liberty Mutual will have loaded all of the ISO (Insurance Services Office) documents into their LLM (large language model) and all the appropriate New Jersey amendments. One, two, three, and you’ll have your quote. I’m not sure you will need an insurance broker until the end of the chat session (and probably only as a matter of law — which the insurance companies will try to change). Of course, a human being may find a different rate structure based on their industry knowledge — but who will you ask to qualify which one is appropriate, correct, or even valid?

Likewise, calls you would make to your primary care physician about your existing health conditions might soon be answered by a “MedChat” AI bot. Need help from Spectrum or Verizon for a problem with your TV, phone, or internet? First stop an AI bot. (I didn’t think anything could be more annoying than the IVR Spectrum has now — but that will change.) Do you need to get a mortgage from your bank? Yes, there’s going to be a bot for that. The list of applications with generalized artificial intelligence will be extensive and pervasive, so much so that some speculate that AI modeling and development will become a $63 billion industry in the next year, growing into the trillions within a decade. And what about those people who looked forward to getting call center jobs to raise themselves out of poverty? They will need to pursue completely different career paths. There is no “next level” for many of these people because building the bots is so complex they won’t have the skills necessary to get hired.

Let’s take a moment to discuss what AI will do in the education field. It isn’t going to be pretty. That’s because what you “feed” the artificial intelligence engine is what provides the basis of responses. Currently, in the United States, high school history textbooks in California contain vastly different explanations of events than those in Texas. This linked article from the New York Times is a few years old but depicts the massive “disconnect” in the study of US history. Guess what? Those same divergent viewpoints will arrive in AI history bots. Will we have a uniformly educated America? No, in fact, it will become even more divergent (and undoubtedly more strident) because some communities will not accept any artificial intelligence software in their educational system.

Two years from now, Windows 10 will go out of service. Microsoft claims that CoPilot applications will be available for Office 365 users for an extra $30 per month. Redmond has designed these apps to help businesses by reading through emails, Word documents, Excel spreadsheets, and PowerPoint presentations. The AI bots will perform data mining of a company’s internal resources to provide additional insight and — they hope — business opportunities and streamline business deals. As an aside, I upgraded my laptop to the latest version of Windows 11 23H2 and saw that CoPilot is in beta mode on my Taskbar. I will report the results of testing in a few months. Having seen this latest change, I realize that all new Windows 11 computers require more memory than I had planned (i.e., 16 GB of RAM instead of 8 GB).

For all we know, Windows 12 will be a cloud-based AI-based agent that allows you to run Windows in any browser on any platform you want. The monthly subscription will probably put off mass adoption — because we know that the folks at Redmond are greedy. But after a while, with appropriate discounts, mass uptake will undoubtedly occur. Then, you can use an AI bot to browse your email, view websites recommended by your reading profile, and work with documents that “understand” who you are.

Yep, that’s pretty freakin’ scary stuff. I’m going to continue to guide you through this huge transition.

Thanks, and safe computing!