MSP Summer School 2027: The AI MSP Make the Successful Transition

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For a number of years I’ve run an MSP Summer School during January.

For January 2027, I want to tackle what I believe is one of the biggest changes the MSP industry has faced:

The transition to becoming an AI-enabled MSP.

AI isn’t simply another product that MSPs need to understand so they can sell it to customers.

I think the change is much bigger than that.

For the past 20 years, MSPs have helped customers navigate major technology transitions. We’ve moved customers from servers to cloud, perpetual licensing to subscriptions, on-premises infrastructure to Microsoft 365 and traditional security models towards Zero Trust.

This time, the MSP itself needs to make the transition.

That’s what the 2027 MSP Summer School will be about.


The AI MSP: Make the Successful Transition

The plan is to run four live online sessions during January:

DateTime
Wednesday, 6 January 202710:00 am–12:00 pm AEDT
Wednesday, 13 January 202710:00 am–12:00 pm AEDT
Wednesday, 20 January 202710:00 am–12:00 pm AEDT
Wednesday, 27 January 202710:00 am–12:00 pm AEDT

That’s eight hours across four Wednesday mornings, with a week between sessions to take what we discuss, try it inside your MSP and come back with the results.

The program will follow a simple progression:

Understand → Build → Sell → Operate

This won’t be eight hours of AI theory.

The objective is to help you start building the AI-enabled version of your MSP.


Week 1: The AI MSP

What does an MSP need to become?

We’ll begin with the strategic question.

What does AI actually mean for the MSP business model?

We’ll look at areas including:

  • how AI changes the way an MSP operates
  • where existing MSP revenue may come under pressure
  • what customers will increasingly expect from their technology provider
  • AI-enabled service delivery
  • Microsoft 365 Copilot, agents and automation
  • opportunities for new recurring services
  • moving towards managed business outcomes
  • Shadow AI, security and governance
  • assessing your current AI maturity

The objective will be to start creating an AI MSP Transition Map for your business.


Week 2: Build the AI-enabled MSP

Use it yourself before you try to sell it

I strongly believe MSPs need to start using AI internally before attempting to advise customers on their own AI transformation.

We’ll therefore get practical.

We’ll look at opportunities across:

  • service desk
  • technical documentation
  • sales
  • marketing
  • proposals
  • account management
  • customer reporting
  • project delivery
  • security
  • administration
  • knowledge management
  • business process automation

We’ll also explore technologies such as Microsoft 365 Copilot, Copilot Chat, Copilot Studio, agents, Power Automate, Azure AI, RAG, private/local AI and MCP.

One question will feature heavily:

Would I currently pay an employee to do this manually?

If the answer is yes, we should at least investigate whether AI can assist, accelerate or automate some of that work.

The objective will be for each participant to identify at least 10 processes inside the MSP that could potentially be redesigned using AI.


Week 3: Selling AI

How do we turn this into revenue?

Using AI internally is only half of the opportunity.

The next challenge is turning AI knowledge and experience into something customers will actually buy.

I don’t think simply offering “AI consulting” or “prompt engineering” is enough.

We need packaged outcomes.

For example:

  1. AI Readiness Assessment
  2. AI Governance Foundation
  3. Microsoft 365 Copilot Readiness and Deployment
  4. AI Productivity Workshop
  5. Business Process Automation
  6. Custom AI Agents
  7. Managed AI Services

We’ll work through customer discovery, demonstrations, packaging, pricing, ROI and the increasingly common objection:

“We’re already using ChatGPT.”

The goal will be for every MSP to leave this session with the foundations of three AI services that could be taken to customers.


Week 4: Operating the AI MSP

Turn the ideas into action

The final week brings everything together.

We’ll explore areas including:

  • AI governance
  • customer data protection
  • identity and access
  • Microsoft Purview
  • DLP
  • Shadow AI
  • agent governance
  • human oversight
  • AI acceptable-use policies
  • quality assurance
  • measuring AI ROI
  • developing staff skills
  • internal AI champions
  • continuous improvement

Most importantly, every MSP should finish January with a:

90-Day AI MSP Transition Plan

That could look something like this.

Days 1–30: Adopt

Start internal AI adoption, establish governance, train staff and identify repeatable use cases.

Days 31–60: Build

Package offerings, create demonstrations, establish pricing and identify pilot customers.

Days 61–90: Sell

Deliver pilots, measure results, capture case studies and start converting successful projects into managed services.

The question at the end of Summer School will be very simple:

What is your MSP going to do differently on Monday morning?


Constant Recording. Constant Iteration.

There’s another idea I want to explore throughout Summer School.

Record → Analyse → Improve → Repeat

Subject to appropriate privacy, consent and governance, MSPs generate enormous amounts of useful information every day:

  • customer questions
  • support interactions
  • meetings
  • sales conversations
  • customer objections
  • procedures
  • documentation
  • repetitive tasks
  • successful prompts
  • failed approaches
  • automation opportunities

Historically much of that information disappeared as soon as the conversation or interaction ended.

AI potentially changes that.

Activity can become knowledge.

Knowledge can produce insight.

Insight can drive automation.

Automation can produce better processes.

That leads to a principle I want to explore throughout Summer School:

Constant recording. Constant iteration. Constant improvement.


You’ll be doing, not just watching

I don’t want this to be four webinars where everyone watches presentations for two hours.

Each session will combine:

  • current AI developments
  • key concepts
  • live demonstrations
  • MSP-specific examples
  • practical workshops
  • group discussion
  • take-home challenges

There will also be work between sessions.

After Week 1

Identify 20 repetitive activities inside your MSP.

After Week 2

Select five and experiment with AI.

After Week 3

Have an AI-focused conversation with three customers.

After Week 4

Choose one AI service to launch.

The goal isn’t simply to attend Summer School.

It’s to start building your AI MSP during Summer School.


What will it cost?

I’m proposing to price Summer School per MSP rather than per person.

That’s deliberate.

I’d much rather an MSP owner bring a technical lead, service manager or salesperson along so that multiple people inside the business understand what needs to change.

Each registration will therefore cover up to three people from the same MSP.

Proposed pricing
RegistrationPrice + GSTSaving
StandardA$895–
Patron memberA$795A$100
AI Dojo memberA$745A$150
Patron + AI Dojo memberA$645A$250

For those who are members of both Patron and AI Dojo, you’ll receive the special combined-member price rather than having to work out multiple overlapping discounts.

Member prices won’t stack with other promotional offers.

I’m also considering an additional post-Summer School implementation clinic for people who are members of both Patron and AI Dojo.


What’s included?

My current plan is for registration to include:

  • four live two-hour sessions
  • up to three participants from the same MSP
  • session recordings
  • practical worksheets
  • templates
  • AI MSP planning resources
  • AI service development frameworks
  • exercises to complete inside your MSP
  • your own 90-Day AI MSP Transition Plan

The emphasis throughout will be firmly on practical outcomes rather than AI theory.


Who is Summer School for?

I’m designing this primarily for:

  • MSP owners and principals
  • practice managers
  • technical leaders
  • service managers
  • sales and business development leaders

You certainly don’t need to be an AI expert.

In fact, that’s rather the point.

If you’re asking questions such as:

What does AI actually mean for my MSP?

Where should I start?

How should we use AI internally?

What AI services should I take to customers?

How can we make money from this?

How do we manage the security and governance risks?

How do I stop AI becoming another technology distraction?

then this is exactly the sort of program I’m planning.


Interested? Register your interest now

At this stage I’m asking MSPs to register their interest.

There’s no commitment simply from expressing interest. It will help me gauge demand for the January program and keep interested people informed as the final agenda, registration arrangements and supporting material are confirmed.

Register your interest in MSP Summer School 2027

If you’re considering joining me in January, register your interest now so I can keep you updated as the program takes shape.


The goal

I’m not going to promise that eight hours of Summer School will magically transform an MSP.

I think there’s a much more useful objective.

By the end of January, I want participating MSPs to understand:

Where they are now.

Where AI could take their business.

What they should use internally.

What they could sell to customers.

What they shouldn’t do.

And, most importantly:

What they are going to do next.

Because the basic premise behind Summer School 2027 is straightforward:

MSPs have spent the last 20 years helping customers make successful technology transitions.

Now it’s our turn.

MSP Summer School 2027

The AI MSP: Make the Successful Transition

6, 13, 20 and 27 January 2027
10:00 am–12:00 pm AEDT
Live online

Standard: A$895 + GST per MSP
Patron: A$795 + GST
AI Dojo: A$745 + GST
Patron + AI Dojo: A$645 + GST

Up to three attendees from the same MSP.

Register your interest

Your Market Needs a Mayor. Why Not You?

A professional standing confidently in a busy town square at golden hour as people turn to them for guidance

Most MSPs I talk to want to be seen as the leader in their patch. They want the referrals, the respect and the clients who call them first. Then they try to get there by being louder. More ads, more logos on more slides, more posts about how great they are. I think that misses the point. Leading a market isn’t a title you claim. It’s a job you do. Think of it as being the mayor of your town, and the mayor’s real job has never been prestige. It’s service. Whoever is most useful gets the role.

Usefulness beats volume

Your clients are drowning in noise right now. Copilot keeps changing. Every week brings a new security scare. Microsoft licensing still confuses people who have bought it for a decade. Nobody needs another voice shouting. They need someone calm who makes sense of it all.

I wrote earlier about how to make your business easier to buy. This is the same idea seen from the other side. When you’re consistently the person who explains things clearly, buying from you stops feeling like a risk. People already trust your judgement before they ever see a quote.

Three jobs every mayor takes on

The way I see it, the work comes down to three habits.

  • Turn fear into confidence. When a scary phishing story hits the news, don’t wait for panicked emails. Send clients a short note covering what it means for them, what you’ve already checked in Entra and Defender, and the one thing they should do.
  • Turn uncertainty into clarity. Picture running a twenty-minute monthly Copilot briefing in Teams. Show what changed, what’s worth trying in Outlook or Word, and what to ignore. No pitch, just clarity.
  • Answer before they ask. If Microsoft is about to change something in Teams or Outlook, you already know the question your clients will raise. Put a plain-English explainer in their inbox first. When licensing shifts again, give them a one-page summary in SharePoint showing what it means for their seats and their budget.

None of this needs a marketing department. It needs attention and a willingness to share what you already know. Copilot can even help you draft these updates faster, as long as the judgement in them is yours.

The rewards follow the service

Here’s what I’ve seen over many years. Status, influence and revenue rarely go to the loudest operator in town. They drift towards the person everyone already relies on. When people know you’ll tell them the truth, they bring you their problems. That’s a far stronger position than any campaign can buy.

It also changes how you sell, or rather how little you need to. In Stop Selling. Start Letting People Decide. I argued that pressure drives good clients away. Being genuinely useful is the opposite of pressure. You give first, consistently, and let people come to you when they’re ready.

Being useful also compounds. Every clear explanation makes the next one more trusted. Every early warning makes clients a little more likely to forward your notes to a colleague. Over time you’re no longer one provider among many. You’re the person the town turns to.

Take the job

So here’s my challenge. Pick your market, whether that’s a suburb, an industry or a niche within Microsoft 365. Then commit to being the most useful person in it. Start this month with one briefing, one explainer or one early warning. Nobody is going to hand you the mayor’s chain. You earn it by showing up and serving. The job is open. Take it today.

Need to Know podcast – Episode 373

In this episode, I look ahead to Microsoft Ignite and the continuing evolution of Copilot, Work IQ, AI agents and cybersecurity, before exploring a bigger question: is AI actually making businesses better, or simply helping them do more things faster? AI isn’t magic pixie dust that can fix broken processes. Before automating, businesses need to identify bottlenecks, simplify and document processes, establish measurable outcomes and decide where AI genuinely adds value. The real opportunity isn’t generating more emails, documents and automation, but using AI to create better outcomes, reclaim valuable time and continuously improve the way the business operates.

Brought to you by www.ciaopspatron.com

you can listen directly to this episode at:

https://ciaops.podbean.com/e/episode-373-effectiveness/

Subscribe via iTunes at:

https://itunes.apple.com/au/podcast/ciaops-need-to-know-podcasts/id406891445?mt=2

or Spotify:

https://open.spotify.com/show/7ejj00cOuw8977GnnE2lPb

Don’t forget to give the show a rating as well as send me any feedback or suggestions you may have for the show

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Copilot & AI

Security

Microsoft 365 & Partners

From CIAOPS

Who Owns the Agent When the Employee Walks Out the Door?

A professional leaving an office tower at dusk, glowing threads trailing from her briefcase back to the building

Here’s a question I don’t think many businesses have asked yet. When you hire your next person, will they be allowed to bring their own agents with them? And when someone leaves, will you let the agents they built in your business walk out the door too?

For years we’ve treated a worker’s toolkit as personal. Their know-how, their shortcuts, their way of working. Agents blur that line badly. An agent can hold skill, but it can also hold memory, data and relationships. That makes the answer far less obvious than it first appears.

The toolkit versus the tenant

I think the cleanest way to start is to split an agent into two parts.

The first part is the pattern. The prompts, the instructions, the way someone has learned to break a job down and hand it to AI. That’s skill. It lives in their head as much as anywhere, and I don’t believe a business can or should claim it. A good tech who has learned how to direct agents well will carry that ability to their next role, the same way they carry their troubleshooting instincts.

The second part is the data. An agent built in Copilot Studio inside your Microsoft 365 tenant, grounded on your SharePoint libraries and connected to your systems, belongs to the tenant. So does what Copilot remembers about how a person works. Microsoft stores Copilot memory in a hidden folder in the user’s Exchange mailbox, inside your tenant, and admins can find it with Purview eDiscovery. That’s a pretty strong hint about where ownership sits.

I wrote recently about the mystery of personal SharePoint skills, which end up stored in a user’s OneDrive. Personal in name, but still sitting in the company’s tenant. Expect a lot more of that.

Memory is where it gets messy

Picture a consultant who has spent two years working with an agent. It knows her clients, their quirks, which contracts are touchy and which projects ran late. Now she moves to a competitor. Should that memory go with her?

My view is no, and not because the business is being greedy. That memory is tangled up with client data, confidentiality obligations and, in many cases, data residency requirements. You can’t neatly pull “how she works” out of “what she knows about our customers”. Until the tools can genuinely separate the two, the memory has to stay.

Treat BYO agents like BYOD

Bringing your own agent in the other direction feels a lot like the early days of bring-your-own-device. The answer then wasn’t a flat yes or no. It was policy, identity and control. Agents need the same treatment. Whose identity does it run under? What data can it reach? Where does what it learns end up? If you can’t answer those, the agent shouldn’t touch your tenant.

What I’d do now

None of this is legal advice, and your lawyer will have views. But there are practical steps any SMB or MSP can take today:

  • Write a simple agent policy covering who can build, bring and share agents.
  • Keep an inventory of every agent, with a named human owner.
  • Add agents and AI memory to your offboarding checklist, right next to mailbox and device handover.
  • Update employment contracts to say what’s portable and what stays.
  • Decide upfront that skills and prompt patterns travel, while data and memory stay put.

The people who learn to work well with agents will be worth more wherever they go. That’s fine. Let them take the skill. Keep the data. Just make sure you’ve written down which is which before someone hands in their notice.

CIA Brief 20261107

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Security

  • Threat actors use agentic AI tooling to find and abuse exposed secrets
    Microsoft has seen attackers use the ARTEX agentic framework to scan public GitHub repos for credentials and API keys, then act on them, in one case going from a GitHub scan to exfiltrating Azure Key Vault data in five minutes. Since 28 October it has also seen service principal sign-ins from 199.19.77[.]84 using stolen multi-tenant app credentials to reach downstream tenants. Hunt service principal and non-interactive sign-ins for the listed IPs in every tenant you manage, and rotate any secret that has ever touched a repo.
    https://www.microsoft.com/en-us/security/blog/2026/11/05/threat-actors-use-agentic-ai-tooling-to-find-and-abuse-exposed-secrets/
  • Inside a malicious Claude Code-branded extension and its persistent SSH backdoor
    A tampered copy of the Claude Code extension (versions 2.1.312 and 2.1.313) sat in the Cursor extension marketplace for about 11 hours on 29 October, adding an attacker SSH key, enabling SSH, opening a reverse tunnel and setting up persistence. The Visual Studio Marketplace and npm packages weren’t affected. If your team or clients use Cursor, check for those versions and remember the keys and persistence can be left behind even when the tunnel failed.
    https://www.microsoft.com/en-us/security/blog/2026/10/30/inside-malicious-claude-code-branded-cursor-extension-persistent-ssh-backdoor/
  • Email threat landscape: Q3 2026 trends and insights
    Microsoft detected about 7.3 billion email phishing threats in Q3, with September up 41% on August, and CAPTCHA-gated phishing coming back via SVG attachments. The standout finding is that around 129 million spoofed messages were delivered because org or user exceptions overrode protection even after they failed authentication. Good reminder to go and audit those “just allow this sender” exceptions in every tenant.
    https://www.microsoft.com/en-us/security/blog/2026/11/05/email-threat-landscape-q3-2026-trends-and-insights/
  • What exploited vulnerabilities have in common: A data-driven analysis of real-world attacks
    Of roughly 383,000 CVEs disclosed since 1999, only about 2,000 (around 0.5%) have been exploited in the wild, and attackers overwhelmingly go after remote code execution, privilege escalation and authentication bypass. Patching is slow while exploitation is fast, and AI will only shorten that window. Worth a look for prioritising patching by impact and exposure rather than just CVSS score.
    https://www.microsoft.com/en-us/security/blog/2026/11/02/exploited-vulnerabilities-common-data-driven-analysis-real-world-attacks/
  • Fake-download campaign uses trojanized installers to deliver monetization payloads
    People searching for cracked software, free games and activators are getting trojanised installers that silently turn their machines into proxy nodes, distributed-computing workers or hosts for bundled “offers”. Nothing groundbreaking, but it’s exactly the stuff that turns up on staff laptops. Turn on potentially unwanted application protection in Defender and block untrusted software sources.
    https://www.microsoft.com/en-us/security/blog/2026/11/03/fake-download-campaign-uses-trojanized-installers-deliver-monetization-payloads/
  • What’s new in Microsoft Security: November 2026
    This month’s Intune and Defender roundup is heavy on agent security: Dynamic Permissions that scope an agent’s authority to its task, Dynamic Agent Risk and Dynamic Conditional Access, plus Microsoft Execution Containers (MXC), now generally available, to contain what agents can touch at the OS level. There are also endpoint elevation and Exposure Management updates. Still early for most SMBs, but this is the toolkit you’ll need once clients start running agents.
    https://www.microsoft.com/en-us/security/blog/2026/11/05/whats-new-in-microsoft-security-november-2026/

Microsoft 365 & Windows

  • Introducing SharePoint tools in Work IQ
    More than 60 native SharePoint operations are now in public preview through the Work IQ MCP server, so Copilot, Copilot Studio and other agents can find, create, organise and share SharePoint content directly. Microsoft says task pass rates went from 70.1% to 84.6% while using 16% fewer tokens. Worth a look if you’re building agents for clients, but remember they’ll be acting on SharePoint with whatever permissions you give them, so tidy up oversharing first.
    https://techcommunity.microsoft.com/blog/SPBlog/introducing-sharepoint-tools-in-work-iq/4569917
  • How Outlook Search is changing: ranking, resilience, and the feedback loop
    Outlook now shows up to seven relevance-ranked results before falling back to date order, across classic Outlook (Current and Monthly Enterprise Channel), new Outlook, the web and mobile, with Mac following in November. Classic Outlook also leans on the local Windows index when the network is flaky. Good to know when users ring the help desk saying “search is broken” and it’s really just ranking differently.
    https://techcommunity.microsoft.com/blog/outlook/how-outlook-search-is-changing-ranking-resilience-and-the-feedback-loop/4568760

Cloud & AI

  • Gemini 4 Carbon: our next frontier model
    Google’s new frontier model leads on cybersecurity benchmarks for finding, exploiting and patching vulnerabilities, and is built for agentic tasks that run for days. Access is starting with a subset of cyber defenders and trusted partners, with wider release later at $2 per million input tokens and $10 per million output tokens. Still early, but models this good at exploitation are exactly why patch windows keep shrinking.
    https://blog.google/innovation-and-ai/models-and-research/gemini-models/introducing-gemini-4-carbon/
  • Humanist AI in practice: A public consultation on our Code of Conduct for MAI Models
    Microsoft AI has published a first draft of the code of conduct that governs how its MAI models are trained and how they should behave once deployed, and is asking for public feedback. It’s built around Mustafa Suleyman’s idea of AI that is “subordinate, aligned, and contained”. Nothing groundbreaking for day-to-day work, but it’s useful context when clients ask how Microsoft’s own models are governed.
    https://microsoft.ai/news/mai-code-of-conduct/
  • Fair use benefits everyone
    OpenAI has rounded up the amicus briefs filed in support of fair use in the New York Times lawsuit, from library groups, the EFF and law professors through to the US Government. The outcome will shape whether AI training on copyrighted content stays lawful. Still early, and it’s one side’s argument, but it’s a case worth following because it affects the tools every client is adopting.
    https://openai.com/index/fair-use-benefits-everyone/
  • Giving every team a data scientist with Grok Bot
    SpaceXSI’s data science team built Data Bot, a shared Team Bot that it teaches through skills covering metrics, experiments and query logic, so anyone can query the warehouse and get answers the way a data scientist would. Experts improve the skills once and everyone benefits. Worth a look as a model for MSPs: package your team’s know-how into a shared bot instead of being the bottleneck.
    https://x.ai/news/data-bot
  • Elon Musk throttles Grok Bot limits due to ‘unsustainably high’ costs
    Over Halloween weekend some Grok Bot users found their weekly usage limits suddenly maxed out, and Musk confirmed it was deliberate because the cost of serving it was “unsustainably high relative to revenue”. No word yet on what the limits will be going forward. Good reminder that AI pricing and quotas are still moving targets, so don’t build client services that assume today’s limits.
    https://techcrunch.com/2026/11/02/elon-musk-throttles-grok-bot-limits-due-to-unsustainably-high-costs/
  • How AI agents run insurance’s back office
    Harper describes always-on ambient agents that wake on events, work on their own cloud computer and drive carrier websites that have no API, the way a broker would. Since September an agent has helped bring more than 200 small businesses current with their premium-finance lender, with a person still signing off before money moves. Swap “carrier portal” for “vendor portal” and you can see how much MSP back-office work this could take on.
    https://www.harperinsure.com/engineering/ambient-agents/

Other

  • What Happens to MSPs When Grok Bot Can Do the Work?
    My latest post takes Harper’s account of running its back office on ambient agents and asks what that means for MSPs when ticket triage, remote repair, tenant checks and reporting can be packaged up and shared. If the instructions become a template anyone can download, the value has to sit somewhere else. I look at what’s left for the MSP, the vendor and the customer.
    https://blog.ciaops.com/2026/11/06/what-happens-to-msps-when-grok-bot-can-do-the-work/
  • How Grok Bot Can Resolve Help Desk Issues Through Remote Desktop
    My latest post walks through having Grok Bot open a remote-support tool like TeamViewer or AnyDesk on its own computer, connect to an approved attended session and fix a user’s Outlook problem itself, then retest and write up the ticket. I also cover the guardrails: identity and consent checks, and treating inbound email as untrusted. It’s a workflow you configure and test, not something that happens just because the bot has an inbox.
    https://blog.ciaops.com/2026/11/06/how-grok-bot-can-resolve-help-desk-issues-through-remote-desktop/
  • One Prompt, Three Tenants: The Benefits of Grok Bot Group Chat
    My latest post shows how I put three tenant bots into one Grok Bot group chat and ran Microsoft’s exposed-secrets hunting guidance across all of them with a single prompt. Each bot checked its own tenant and the answers came back side by side. I also explain why an invalid or expired secret error on its own doesn’t prove compromise.
    https://blog.ciaops.com/2026/11/06/one-prompt-three-tenants-the-benefits-of-grok-bot-group-chat/

After hours

SpaceX – “GO FOR ORBIT” Documentary – https://www.youtube.com/watch?v=wlWF7kJokvk

Editorial

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Watch out for the next CIA Brief next week

Your Agents Will Outnumber Your People

An IT administrator facing a vast glowing wall of identity nodes multiplying outward from a few people

Most of the businesses I work with know roughly how many user accounts they have. They know who joined last month and, if they’re doing it right, who left. Ask the same people how many AI agents are working in their tenant and the room goes quiet. That silence is the problem I want to talk about, because I think agents are about to become the fastest growing identity population in every business.

Agents are identities, not features

An agent that reads mail, files documents in SharePoint, updates a Planner board or posts into Teams is acting inside your environment. It needs access, and that access has to be granted, scoped, watched and eventually removed. In other words, it needs to be managed like a user.

Microsoft has made this explicit. Microsoft Entra Agent ID, now generally available, gives AI agents their own identities in Entra. Each agent identity is created from an agent identity blueprint, and that blueprint must have a sponsor: a person or group who is accountable for the agent. Conditional Access and Entra ID Governance are being extended to cover agent identities too. I like that design, because it forces the question every business should be asking anyway: who owns this thing?

I’ve been living this myself. I recently wrote about running Microsoft 365 connections headless for autonomous agents, and the first thing you realise is how much power a non-human identity can hold.

The maths changes everything

Here’s the bit that worries me. Picture a 20-person firm. Today that’s 20 accounts to look after. Now imagine each person runs three to five agents: one triaging their inbox in Outlook, one building reports in Excel, one built in Copilot Studio to answer client questions, another chasing approvals in Power Automate. That’s potentially 60 to 100 agents, with no new hires. The headcount stays flat while the identity count multiplies.

We already struggle with user sprawl. Agent sprawl will arrive faster and quieter, because creating an agent feels like a productivity win rather than an IT event.

Where it goes wrong

The failure modes are predictable:

  • Orphaned agents. A staff member leaves, their account is disabled, but the agents they spun up keep running with nobody watching.
  • Over-permissioned agents. It’s easier to grant broad access to get something working than to work out the least privilege it actually needs.
  • No inventory. Nobody can list what exists, what it touches or why.
  • Hidden cost. Agents consume licences and capacity, and the bill grows without a clear owner.

These are the same identity hygiene issues we’ve fought for years, just bigger and faster.

What I’d do now

For SMBs, and especially for MSPs looking after them, I’d treat agents exactly like people from day one:

  • Every agent has a named human owner. No owner, no agent.
  • Use a consistent naming convention so you can tell what an agent does at a glance.
  • Keep an inventory and review it, just like an access review for staff.
  • Grant least privilege and apply Conditional Access where you can.
  • Add agents to your offboarding checklist. When someone leaves, their agents get reassigned or retired.
  • Monitor activity, and use tools like Purview and Defender to keep an eye on what data agents touch.

MSPs have a real opportunity here. Customers will need someone to count, govern and tidy up their agents, and that’s work that fits neatly beside the identity management we already do.

The businesses that win with AI won’t be the ones with the most agents. They’ll be the ones who still know what every agent is doing and who answers for it. Start counting now, while the number is still small.

What Happens to MSPs When Grok Bot Can Do the Work?

MSP leader reflecting on industry change while a team works in the background

Harper Insurance’s engineering team published a detailed account of how they run much of their brokerage back office with ambient agents on Grok Bot. That is insurance, not managed services. Still, if you run an MSP, you should read it carefully. Not because their results automatically transfer to your business, but because the operating model they describe is coming for work that looks a lot like ours.

The uncomfortable question is simple. If tools like Grok Bot can take care of a large slice of MSP work, and if the instructions for that work can be packaged and shared, what is left for the MSP, for the vendors that sell us tools, and for the customer who can download the same template?

What Harper says they built

In How AI agents run insurance’s back office, Harper describes ambient agents that do not wait for someone to type a prompt. Events wake them: an email lands, a customer replies, a deadline gets close. The agent works on its own cloud computer, with a real browser, and can act through websites that have no public API the way a broker would click through a portal.

They also describe an agentic harness around those agents: exploration of portals, typed copies of portal data, an abstraction layer that hides whether a carrier has an API or only a login, and mirroring so agents plan from a trusted copy and act on the live page. On premium-finance rescues, Harper’s account is that since September 2026 an ambient agent helped bring more than 200 small businesses current with their lender, covering over half a million dollars in annual premium, with none cancelled by the lender, and that a person still signs off before money moves.

That is Harper’s account of Harper’s business. It is not independent proof that every agentic workflow is reliable, cheap or transferable. It is evidence that at least one company is already treating Grok Bot as the place where back-office work gets done, not just discussed.

Map that onto an MSP

Now put the same pattern next to managed services. Ticket intake and triage. Remote desktop repair. Tenant checks across Entra, Intune, Defender and Outlook. Monthly reporting. Chasing renewals and missing approvals. Much of that work is event-driven. It spans documented Microsoft 365 APIs, scripts and some portal-only steps. Agents can coordinate those paths and, when needed, use approved desktop control. None of that removes licensing, service permissions or the need for authorised access.

I have already been writing about pieces of this. The How Grok Bot Can Resolve Help Desk Issues Through Remote Desktop guide describes how a bot can operate a compatible, approved remote-support session from its own computer. The screenshot and walkthrough in One Prompt, Three Tenants: The Benefits of Grok Bot Group Chat show one prompt producing separately scoped replies from tenant bots in a shared room. Those posts are about emerging workflows and deployment design. Publishing them is not proof that a production fix was executed end to end, and they are not independent validation that every ticket or hunt already runs unattended. They do show where technician work can start to move into the bot.

If that keeps expanding, I expect labour-per-device and labour-per-seat to stop being comfortable planning assumptions. Repetitive click-work erodes first. Undocumented know-how erodes next, because once a workflow is written as skills and tests, it can be repeated without the original person in the chair. Customers can self-serve common tasks, or need fewer people for them. Some work you currently outsource may come back in-house as a bot you operate. None of that means every MSP disappears, or that every task is already autonomous. It does mean the billable centre of gravity can move.

What happens when MSP bot templates get shared widely

Templates make the shift sharper. A Grok Bot template can package generalised memories, skills, routines and plugins into a shareable copy another business can import. Sharing a workflow does not confer the original owner’s account access. The recipient has to connect and authorise their own accounts, answer setup questions and earn the rights the workflow needs. Anyone creating or importing a template should review what is shared and make sure secrets, credentials and client-specific data are not packed in. Template access is still not the same as tenant access, vetted deployment, ongoing reliability, business context, tests or accountability.

I am not claiming a mature MSP template marketplace already exists, or that every useful MSP capability is cleanly exportable. The scenario we have to face is still real: when a method that used to live only in a senior technician’s head, or only inside a vendor’s product UI, becomes a downloadable bot template, then competitors and customers can acquire the same starting point. The scarce asset stops being “I know which buttons to press” and becomes “I can prove this runs safely in your environment, recovers when it fails, and someone accountable owns the outcome.”

Ask yourself the blunt version. If your client can download the bot instructions for password resets, mailbox restores, Intune compliance chasing or Entra sign-in hunts, what are they still buying from you?

Pressure on third-party MSP tools

Professional services automation (PSA), remote monitoring and management (RMM), documentation and reporting products have spent years encoding workflow into screens. An agent that can use those screens, or reach some of the same outcomes through documented APIs and scripts, exposes how much of the paid value was navigation and repetition. Seat-based economics can feel that pressure if fewer technicians need to live in the console all day. Automation layers that only saved clicks become less special when the bot is the one clicking.

That is not the same as saying Grok Bot replaces RMM agents, backup platforms or endpoint detection and response (EDR). It does not magically erase MFA, licensing, connectors, service permissions or approvals. Distinguish an agent taking over the use of a tool from replacing the tool’s underlying service. Endpoint presence, durable records, audit trails, rollback, security controls and legal obligations still matter. Vendors that offer reliable, agent-ready execution and evidence may stay valuable. Vendors that only sell a nicer sequence of forms may not. Some will bundle agent capabilities themselves. I would plan for fewer technician seats and pressure on per-seat or per-workflow pricing, rather than pretend those shifts are already measured facts about any named product.

What an MSP can do now

Here is where I would start.

  • Map services by automatable outcome. Separate work that is mostly sequence and evidence from work that is judgment, relationship or regulated accountability.
  • Pilot in an approved test environment. Baseline quality, cost, latency, error rate and rollback before you promise a client anything.
  • Version the templates and the tests. If the workflow is worth running, it is worth knowing which revision ran and what proved it.
  • Sell measured service levels, risk handling and outcomes, not keystrokes. AI efficiency does not automatically preserve the old price.
  • Keep the hard parts close: business-specific integration, recovery and security responsibility, exceptional cases, and human approval where money, identity or destructive change is involved.
  • Offer operated and customer-operated configurations deliberately. Some clients will want you to run the bots. Some will want the template and their own operators. Pretending only one model exists is how you get surprised.

Be honest about the economics. Some revenue can shrink even if you adopt AI well, because customer power rises when the instructions are portable. The MSP that survives is not the one that denies that. It is the one that still has something worth buying after the clicks are gone.

My take

Harper’s post is a glimpse of a back office that wakes when work arrives and only interrupts people for the decisions that matter. MSPs are not insurance brokerages, and Grok Bot will not swallow Microsoft 365, endpoint security or compliance overnight. But if ambient agents can work portals, email and desktops, and if MSP templates travel, then undifferentiated technician labour and tool-navigation value can get cheaper for everyone, including your customer. Plan for that world now: prove outcomes, keep accountability, and stop pricing as if the rare skill is knowing which menu to open.

One Prompt, Three Tenants: The Benefits of Grok Bot Group Chat

Security professionals comparing investigation results across multiple screens

Microsoft published a Threat Intelligence post on threat actors using agentic AI tooling to find and abuse exposed secrets. Buried in the mitigation guidance is a concrete hunting ask: review Entra service principal and non-interactive sign-in logs for two campaign IPs, include failed attempts, and pay attention to certain secret-related sign-in errors. For an MSP with several tenants, that usually means opening a separate chat for each tenant, pasting the same ask again and again, and then trying to compare answers that arrived with different context. In the example below I used three tenant bots; the number simply matches that screenshot.

I did something simpler. I put my separate tenant bots into one Grok Bot group chat and pasted a single investigation request. CIAOPS AU, CIAOPS Labs and CIAOPS 365 each replied for the tenant they already know how to query. One prompt. Three independently scoped investigations. Comparable replies in one thread.

What the group chat screenshot shows

In the example shown below, I pasted this prompt, based on Microsoft’s detection and hunting guidance from the 5 November 2026 Microsoft Security blog:

Review Entra service principal and non-interactive sign-in logs for 199.19.77[.]84 and 199.19.77[.]18 including failed attempts. Sign-in errors AADSTS7000215 (invalid secret) or AADSTS7000222 (expired secret) indicate someone holds a credential for your app; a failure followed by a success is urgent.

That last sentence is how the Microsoft article phrases the hunting tip. It is useful as an escalation cue, but it is also easy to over-read. An invalid-secret failure means an invalid secret was presented. It does not, on its own, prove that someone holds a valid working credential. An expired-secret failure means the presented secret was rejected as expired. Microsoft Learn documents AADSTS7000215 as an invalid client secret and AADSTS7000222 as expired client secret keys; see client secret troubleshooting. Successful authentications from these IPs deserve urgent assessment even without a preceding failure. A failure followed by a success for the same relevant identity and context is also urgent. Neither pattern, and neither IP alone, proves compromise. Microsoft notes that 199.19.77[.]18 is a Tor exit node and may include unrelated activity, so an IP match is an investigation lead rather than conclusive maliciousness. Failed attempts remain reportable; they are not automatically benign.

The valuable part of the screenshot is that the bots did not just search. They qualified the prompt as they worked.

Screenshot of a Grok Bot group chat where CIAOPS AU, CIAOPS Labs and CIAOPS 365 each reply to one shared Entra sign-in investigation prompt
One shared investigation prompt in a Grok Bot group chat. CIAOPS AU, CIAOPS Labs and CIAOPS 365 each reply for their own tenant. Click for the full-resolution original.

In the example shown, reported around 6 November 2026 at about 11:30 am Sydney time (AEDT):

  • CIAOPS AU checked ciaops.com and reported neither IP in service-principal, non-interactive or managed-identity sign-ins for 7 Oct to 6 Nov. It found no matching 7000215 / 7000222 results or failure-followed-by-success sequences. It also noted that Microsoft Sentinel returned no matches, while its service-principal history only started on 21 Oct, whereas non-interactive coverage spanned the fuller window.
  • CIAOPS Labs checked ciaopslabs and reported no matches for either IP across service principal and non-interactive sign-ins for the same window. It also clarified the error-code meanings against Microsoft documentation.
  • CIAOPS 365 checked ciaops365.com through Microsoft Defender and reported neither IP in the last 30 days of available Entra data through that path, with no matching error codes or failure-to-success sequences.

Those are results reported in that chat at that time, not a fresh re-verification of the tenants as I write this, and not a claim that the tenants are clean forever. No matches in available logs is not proof of no compromise. Coverage gaps matter, which is exactly why AU calling out shorter Sentinel service-principal history is useful.

What group chat adds for MSPs

Separate chats still work. Group chat changes the operating model.

  • Less repetitive prompting. You paste the intelligence once instead of rewriting or copying it into every tenant conversation.
  • Consistent questions across clients. Every bot sees the same IPs, error codes, time window intent and urgency language.
  • Visible source coverage differences. One tenant answers from Entra plus Sentinel, another from Defender’s available window. You see the gap in the same thread instead of discovering it days later.
  • Follow-up in one place. Ask AU to explain the shorter history or query older archived data if it is already available, or ask Labs to include managed-identity logs, without losing the Labs and 365 answers.
  • Checking conclusions. When one bot softens an overstated prompt and another finds a data-retention limit, you can challenge both answers in front of the whole group.
  • Delegated specialists with bounded permissions. Each bot keeps its own authenticated, least-privilege connection to its tenant. The group is coordination across separately scoped bots.

Adding a bot to a group does not grant new tenant access. The queries still run through whatever authenticated connections, scripts and permissions that bot already has. If a bot cannot read service principal sign-ins in its tenant, the group chat will not invent that ability.

Prerequisites: separate, correctly scoped tenant bots

Before the group is useful, each tenant bot needs its own working, correctly scoped Microsoft 365 access. That usually means separate identities, connectors or certificate-based scripts, and clear rules about what the bot may read and what it must never change. I walked through the secure connection pattern in How to Connect Grok Bot to Microsoft 365 Securely, and the Conditional Access side of bot sign-ins in Using Grok Bot with a Conditional Access Geo-Block.

The group shares investigation context; it does not combine credentials or permissions.

How I used the group for this hunt

  1. Put the right bots in one group. I used a Grok Bot group chat that already contained CIAOPS AU, CIAOPS Labs and CIAOPS 365. Keep membership deliberate. A cross-client group means each participant can see the shared prompt and the other bots’ replies.
  2. Paste sourced intelligence once. I used the Microsoft hunting tip as the seed, then made sure each bot understood it was to investigate only its assigned tenant.
  3. Read the replies side by side. Look for matches, near misses, coverage windows, source differences and whether the bots corrected the prompt.
  4. Follow up on limitations. Where history starts later, ask the bot to explain the shorter history or query older archived data if it is already available. A prompt cannot recover unretained or uncollected data. Official Entra activity-report retention is limited in-portal unless you archive elsewhere; Free is much shorter than P1/P2, and longer retention depends on routing logs to storage or analytics. See Microsoft Entra data retention.
  5. Keep remediation human-led. No automatic incident closure, no secret rotation, no public posts, and no changes unless a human authorises them.

A better copyable prompt

If I were sending the same hunt again, I would tighten the wording so every bot gets the same scope and evidence bar. Something like this:

@CIAOPS AU @CIAOPS Labs @CIAOPS 365

Microsoft Threat Intelligence published hunting guidance for service-principal credential abuse activity associated with 199.19.77[.]84 and 199.19.77[.]18 (see the 5 Nov 2026 Microsoft Security blog on agentic AI tooling and exposed secrets). Addresses are defanged for display; use normal IP literals in log query filters. Do not contact the addresses.

Each of you: investigate ONLY your assigned tenant with your existing authenticated read-only access.

For the widest available lookback your sources allow, review:
- Entra service principal sign-ins
- Entra non-interactive sign-ins
- Any other related sign-in tables you can already query (for example managed identity), naming each source

Search for both IPs above. Include failed and successful attempts.

For any hits, report: timestamp, app/service principal identifiers you are allowed to show (no tenant or app GUIDs in public write-ups), IP, result/error code, resource if available, and whether a failure was followed by a success for the same relevant identity/context.

Treat AADSTS7000215 as an invalid client secret presentation, and AADSTS7000222 as an expired client secret presentation. Do not claim either code alone proves possession of a currently valid secret.

Flag successful authentications from these IPs for urgent assessment even without a preceding failure. Also treat a failure followed by a success for the same relevant identity/context as urgent. Neither that pattern nor an IP match alone proves compromise. Failed attempts remain reportable; they are not automatically benign. Still present evidence rather than a verdict. Microsoft notes 199.19.77[.]18 may be a Tor exit node with unrelated activity.

Also report, per source: earliest and latest event time available, total records scanned if known, and any coverage gaps (ingestion start date, 30-day caps, Sentinel vs portal differences). Explicitly flag query failures or inaccessible sources; do not return "no matches" when the query failed.

Do not make changes. Do not rotate secrets. Do not close incidents. Do not send email or post externally. Return evidence only.

That prompt names the bots, forces per-tenant scope, asks for failed and successful attempts, treats successful IP hits as urgent without requiring a prior failure, demands coverage metadata and honest query-failure reporting, and forbids remediation. It also keeps the credential and Tor-exit nuances honest.

Why the error-code nuance matters

Service principal sign-ins are the app-only authentications where certificates or client secrets are used. Microsoft documents that category separately from interactive and non-interactive user sign-ins; see service principal sign-ins. In a campaign like this, failed secret attempts can be noise, probing, stale automation or someone holding an old value. Successful authentications from a campaign IP are a different severity.

In the example chat, all three bots pushed back on the oversimplified “invalid secret means someone holds a credential” reading. That is exactly the behaviour I want from specialists in a group: search hard, then refuse to overclaim.

Least privilege, privacy and what group chat is not

  • Least privilege still wins. Each tenant bot should only have the read permissions needed for hunts like this. Group membership is not a reason to widen Graph or Sentinel rights.
  • Visibility is a design choice. In a cross-client group, every member can see the shared prompt and the replies. Do not put unrelated customer secrets, ticket notes or personal data into that room.
  • Group membership does not equal unrestricted access across tenants. Each bot still only reaches what its own connections allow.
  • No automatic sending or incident closure. The point of the pattern is faster, comparable investigation evidence for a human to act on.

My take

The benefit of Grok Bot group chat is not that AI suddenly understands Microsoft security better. It is that one piece of threat intelligence can be turned into several bounded tenant investigations without me re-explaining the ask each time. The bots bring their own connections, correct soft language in the prompt, and surface coverage differences that would otherwise hide in separate threads. Use that for hunting. Keep remediation, secret rotation and incident decisions with people who own the risk.