Dom Kirby, CISSP, SSCP

Beyond the Helpdesk: Reimagining MSP Value in the Age of AI From the AI bubble pop to the life-or-death reality of cyber hygiene, see why 2026 will force MSPs to pivot or drown.

Empowerment without visibility isn't innovation; it’s just deferred incident response.

We have to reframe our value around business outcomes to win in 2026.

Check out the full breakdown and my 2025 retrospective here: domkirby.com/blog/ms...
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Key shifts to watch: 🛡️ Cyber Realism: Focus on the Risk Register over vanity features. 🔑 Identity Core: Securing the "Agents" and automations in your environment. 🧠 Talent Pivot: Hiring for process mapping, not just engineering.
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Beyond the Helpdesk: Reimagining MSP Value in the Age of AI From the AI bubble pop to the life-or-death reality of cyber hygiene, see why 2026 will force MSPs to pivot or drown.

2026 will be a year of "Managed Intelligence" and deeper advisory. To stay ahead, MSP leaders must navigate some critical shifts.

I’ve laid out my full roadmap for the industry—from the AI bubble to the risk register.

Link: domkirby.com/blog/ms...
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New enhancement to my blog workflow, I now have a workflow in #n8n to automagically convert the Google Doc and start a draft in WordPress!

Original Post/Workflow: domk.pro/zlcbct?utm_...

The basics of securing your clients' environments with #AI or even #Agents onboard haven't changed. It's the same 5 things we've been begging for for YEARS.

If the basics aren't covered, nothing you do specifically for AI protection matters, because it's built on no foundation.

2025 is the first "Year of the AI Agent" I'm told. So, my first 2026 AI prediction, we'll see the first companies post entry level roles demanding ten years of agent implementation experience.

In 2025, tech giants decided smart glasses are the next big thing As we near the end of 2025, it's becoming increasingly apparent that smart glasses are going to be the next "big" thing. Here's why.

Anyone keeping count of how many times "smart glasses" will be the next big thing? Maybe it'll stick this time.

Flock cameras remained active in two cities where officials had asked for them to be turned off Officials in Cambridge, Massachusetts, and Eugene, Oregon, found that some Flock Safety license plate readers were still active after the municipalities asked for services to be terminated.

I would say it sounded like a good idea at first, but it really didn't. Flock is a total disaster and a complete misapplication of good intention...

Nearly 20 million affected by Prosper, 700Credit data breaches Fintech company Prosper Marketplace and car dealership services provider 700Credit are the latest financial institutions to report data breaches affecting millions of Americans.

AI doesn't change cyber fundamentals. At all. The 700Credit breach seems to be the result of shitty supply chain, 5 million records. The breaches will continue until hygiene improves.

Coupang data breach traced to ex-employee who retained system access A data breach at Coupang that exposed the information of 33.7 million customers has been tied to a former employee who retained access to internal systems after leaving the company.

Thou shalt test, test, and retest thou's user termination processes!

Of all the things that for sure did not happen, DNS did not double your speed 🙄

🔥This is either an affirmation or a hot take, but you need to hear it either way...

Azure Files was meant to replace a file server IN AN AZURE NETWORK. It is not meant for direct remote access over a VPN.

That is all.

How I Use AI to Write (Without Losing My Voice) I don't want to just put out 'AI slop.' Here is the N+1 rule I use to write, edit, and validate my content with AI (without losing my voice).

I refuse to post "AI Slop." 🚫

But I do use AI to help. My secret is the N+1 Rule:

Write the draft (me).

Edit with Gemini.

"Blind Judge" with ChatGPT.

AI isn't the writer; it's the editor.

Here is my exact workflow (including the prompts I use): domkirby.com/?p=2019

#AI #Writing #Workflow

Moving a messy S: Drive to SharePoint isn't modernization.

It’s a Tech Debt Balance Transfer. 💳

You didn’t fix the problem; you just moved the interest payments to a new account.

Stop migrating the mess. Start paying down the debt. 👇 domkirby.com/blog/te...

#MSP #TechDebt

Agents vs. Workflow Automation: Stop Over-Engineering Your MSP Many MSPs are overpaying for "AI" when a simple script would do the job. Here is the secret to deciding which one your client actually needs (and can afford).

Read the full breakdown on when to use which (and how to spot the trap): domkirby.com/blog/ai...

#MSP #Automation #AI #BusinessStrategy
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If your client is asking for "AI" just to have it, they are buying vanity, not value . And if they are still running legacy apps like desktop QuickBooks? That fancy Agent is going to fall apart the second you deploy it.


Stop over-engineering. Start asking "Why?"
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I just published a breakdown of the difference, but here is the short version: An Automation is static. It does X, then Y. It’s boring. It works. An Agent thinks. It makes decisions. It’s powerful, but it costs at least twice as much to build and twice as much to operate.
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We’re obsessed with #Agents. Clients are asking for them, and vendors are selling them hard.

But here’s the uncomfortable truth: Many small businesses don’t need an Agent. They need a workflow automation that creates value.
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Yes, Hello For Business Constitutes MFA Is Windows Hello really multi-factor authentication? Short answer: yes. NIST defines it as a multi-factor cryptographic authenticator, combining something you have with something you are or know. Lear...

Yes, Windows Hello is MFA! domkirby.com/blog/hello-m...

Nobody Cares About Your Tech Stack - Dom Kirby The almighty tech stack. The best EDR, rock solid email security. “Enterprise technology for the SMB.” I could go on for a while with all the clichés, and I used many of them. I was a technical buyer,...

Many MSPs make the same mistake: they sell the stack.

But your clients don’t care about your EDR, your email security, or your “enterprise tech for SMB.” They care about outcomes: revenue, efficiency, and risk reduction.

Latest blog post 👉 domkirby.com/blog/msp-bus...

#MSP #AI #BusinessOutcomes

I remember this! So many things about Windows Phone were so good - aside from the strategy to get it in market 😞

We see you've had a heavy lunch. For this next mission (meeting), you'll need to fight the overwhelming urge to take a nap.

I'm leaning towards Mac myself but want to make a slow/methodical decision for once 🤣.

Curious, how are you finding gaming on Ubuntu?

This isn't meant to be an "anti-Microsoft" rant, but as a long time Windows user, I increasingly feel like the product is neglected and being repurposed away from being the natural OS of choice.

Is this a conscious choice by Microsoft, or an unintended consequence of such massive change?

Windows is a Mess - Dom Kirby I’ve been a Windows user for as long as I’ve been a computer user for the most part. I’ve dabbled in Mac, used plenty of Linux distros. But, day-to-day, I still use Windows. Windows XP was the first O...

👀 Is Microsoft quietly moving on from Windows?
Between #AI and Microsoft’s cloud & datacenter pivot, it feels like Windows — the product that made Microsoft into Microsoft — is just a delivery engine for other stuff.
👉 domkirby.com/blog/windows...

Can your MSP Communicate Outages Out of Band? - Dom Kirby Over the weekend (on 3/1 to be exact), there was a significant outage at Microsoft impacting primarily Exchange Online but also some other services. Even though this outage was relatively short, many MSPs reported receiving lots of emergency calls, texts, tickets, etc. With that in mind, have you thought about how you communicate outages to […]

Do you have a way to communicate with clients when the email goes down? Last weekend's Microsoft outage reminded me of the value of the humble status page.

domkirby.com/blog/ou...

#MicrosoftOutage

How to migrate to the Authentication methods policy - Microsoft Entra ID Learn about how to centrally manage multifactor authentication and self-service password reset (SSPR) settings in the Authentication methods policy.

The legacy MFA and SSPR settings are moving to the Authentication Methods policy on 9/30/2025, definitely something you'll want to get ahead of to avoid any potential workflow interruptions: learn.microsoft.com/...

#EntraID

This is why #AdBlockers can be a helpful security tool. This ad for a "PC App Store" was conveniently placed next to the download button for Notepad++

It's a response to an increase in human operated attacks that make small amounts of noise BEFORE the boom. Find the noise.
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Qualified humans making qualified calls about suspicious activity can be the difference between a "boom" and "no boom" incident.

Rapid isolation and eradication are essential. So, when I go out and say, "you need #MDR," it's not a play for money.
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