Need to Know podcast–Episode 359

I am joined by Andrew and Tim from Sherpatech to discuss updates and new challenges in the insurance market. If you missed last year’s episode you’ll find it here Episode 338 – Ensure to Insure. We discuss what impact AI is likely to have and how the insurance market is shaping up for 2026. I also have a few interesting updates and information from the Microsoft cloud for this first episode of 2026. So listen along and enjoy!

Brought to you by www.ciaopspatron.com

you can listen directly to this episode at:

https://ciaops.podbean.com/e/episode-359-reinsurance/

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Resources

Explore the tools, communities, and content mentioned in this episode:

CIAOPS Need to Know Podcast: https://ciaops.podbean.com/
CIAOPS Blog: https://blog.ciaops.com/
CIAOPS Labs: https://blog.ciaopslabs.com/
CIAOPS Brief: https://blog.ciaops.com/tag/cia-brief/
Join the Teams Shared Channel: https://blog.ciaops.com/2022/07/29/join-my-teams-shared-channel/
CIAOPS Merch Store: https://my-store-c5d877-2.creator-spring.com/
CIAOPS Publications: https://directorcia.gumroad.com
Become a Patron: https://www.ciaopspatron.com/
Direct Support: https://ko-fi.com/ciaops
Get Your M365 Questions Answered: https://blog.ciaops.com/2025/06/11/get-your-m365-questions-answered-via-email-2/
Test Your Microsoft 365 Speed: https://blog.ciaops.com/2025/07/21/test-your-microsoft-365-speed-in-seconds-for-free/
CIAOPS Email list – https://bit.ly/cia-email

Show Notes

‘AI adoption is accelerating, but confidence is collapsing’: The more workers use AI, the less they trust it. Baby boomers show a 35% drop

Data Security Posture Management for AI | Microsoft Community Hub

GitHub Copilot CLI

Bringing work context to your code in GitHub Copilot – Microsoft for Developers

PowerShell script to extract M365 security data for your own AI analysis – CIAOPS

Essential 8 AI report via PowerShell – CIAOPS

Unlocking Microsoft 365 Security: How I Automated AI-Powered Risk Analysis with PowerShell

YouTube

Microsoft and Mercedes-AMG PETRONAS F1 Team unite to drive innovation from factory to circuit – Source

Microsoft OneDrive, a year in review: AI-powered file management and smarter collaboration

Demystifying Exchange Online Mailbox Quotas | Microsoft Community Hub

SherpaTech

Insurance Health Check

MSP/ IT Professional Insurance Quote and Policy portal

Insurance Checklists

Unlocking Microsoft 365 Security: How I Automated AI-Powered Risk Analysis with PowerShell

Video URL – https://www.youtube.com/watch?v=gyPXlI6GHCo

In this video, I walk you through my exclusive PowerShell script that transforms Microsoft 365 security management. Watch as I extract real-time security data from my Microsoft 365 tenant, summarize it, and seamlessly upload it to a custom AI Foundry agent powered by GPT-5. You’ll see how I authenticate using Azure AD, leverage model routing for the best AI analysis, and generate a detailed, actionable HTML security report—complete with risk assessments, prioritized recommendations, and remediation guides. This tool is available only to subscribers, so if you want to supercharge your Microsoft 365 security with AI automation, this is a must-watch! Drop your questions in the comments and discover what’s possible when PowerShell meets next-gen AI. See the blog post at – https://blog.ciaops.com/2026/01/22/co…

Essential 8 AI report via PowerShell

I recently provided a PowerShell script to extract M365 data for your own AI analysis. Also as part of that I provided two recommended prompts you can use to generate a report based on that data. I have now added an Essential 8 prompt you can use to generate a detailed Essential 8 analysis and report, which you an find here:

https://github.com/directorcia/Office365/blob/master/Analysis/Secure%20Score/prompt-e8.txt

You can see the result of this prompt in the images provided, which in this case was used with Copilot Researcher with Claude.

You can of course, use this prompt with any AI you prefer and just use it as a starting point and customise to suit your needs

If you have any further suggestions for prompts with this extract security data please let me know.

CIA Brief 20260124

Exchange Online Public Folder Data and Retention Questions –

https://techcommunity.microsoft.com/blog/exchange/exchange-online-public-folder-data-and-retention-…

Inside the takedown of RaccoonO365: How Phishing-as-a-Service fuels ransomware’s engine –

https://www.microsoft.com/en-us/corporate-responsibility/topics/cybersecurity/stories/raccoono365/

Inside the takedown of RaccoonO365: How Phishing-as-a-Service fuels ransomware’s engine –

https://www.microsoft.com/en-us/corporate-responsibility/topics/cybersecurity/stories/raccoono365/

Ford builds trust across global operations with Microsoft Defender –

https://www.youtube.com/watch?v=55tcTDO1Sbw

Microsoft and Mercedes-AMG PETRONAS F1 Team unite to drive innovation from factory to circuit –

https://news.microsoft.com/source/2026/01/22/microsoft-and-mercedes-amg-petronas-f1-team-unite-to-d…

Microsoft Security success stories: Why integrated security is the foundation of AI transformation –

https://www.microsoft.com/en-us/security/blog/2026/01/22/microsoft-security-success-stories-why-int…

Message Trace Support Using Graph API is now in Public Preview –

https://techcommunity.microsoft.com/blog/exchange/message-trace-support-using-graph-api-is-now-in-p…

Automating Microsoft Sentinel: A blog series on enabling Smart Security –

https://techcommunity.microsoft.com/blog/microsoftsentinelblog/automating-microsoft-sentinel-a-blog…

Microsoft OneDrive, a year in review: AI-powered file management and smarter collaboration –

https://techcommunity.microsoft.com/blog/microsoft365insiderblog/microsoft-onedrive-a-year-in-revie…

After hours

Free climbing in Greenland – https://www.youtube.com/watch?v=ep-xRQDTiOg

Editorial

If you found this valuable, the I’d appreciate a ‘like’ or perhaps a donation at https://ko-fi.com/ciaops. This helps me know that people enjoy what I have created and provides resources to allow me to create more content. If you have any feedback or suggestions around this, I’m all ears. You can also find me via email director@ciaops.com and on X (Twitter) at https://www.twitter.com/directorcia.

If you want to be part of a dedicated Microsoft Cloud community with information and interactions daily, then consider becoming a CIAOPS Patron – www.ciaopspatron.com.

Watch out for the next CIA Brief next week

PowerShell script to extract M365 security data for your own AI analysis

I wrote about how I have now integrated PowerShell and AI recently:

https://blog.ciaops.com/2026/01/22/combining-powershell-and-ai-for-m365-security-analysis/

In that example, I use my own agent developed in Azure AI Foundry to analyse security data extracted from Microsoft 365. In there I did offer free access to the script and my Foundry AI agent for analysis. However, I do appreciate that many people are hesitant to allow a ‘foreign’ AI system to evaluate private M365 security data.

Therefore, I have created another script that will simply extract your M365 security data and put it into a local JSON file that you can then upload to your own AI for analysis. You will find that script at:

https://github.com/directorcia/Office365/blob/master/Analysis/Secure%20Score/o365-secure-score-extract.ps1

and the documentation is here:

https://github.com/directorcia/Office365/wiki/Extract-Microsoft-365-Secure-Score-information

To use this script you need to have the PowerShell Graph module installed and use an account that has appropriate access to M365 security information.

When run, you’ll see it extract the security from various places in the tenant as shown above.

It will then save that information to a local file as shown above.

In this case you’ll see that I used the –compact option to two data files. The normal one, which is around 8MB and a smaller one around 234KB. The reason for this is that I found in my testing that many AI systems don’t support large file uploads (M365 Copilot does but). So the smaller one can work with those limited systems.

Once you give your AI system of choice access to the data file by uploading it, you can then use any prompt you wish to analyse the data. Here are some prompts I have created you can use. A long one:

https://github.com/directorcia/Office365/blob/master/Analysis/Secure%20Score/prompt-long.txt

and a shorter one:

https://github.com/directorcia/Office365/blob/master/Analysis/Secure%20Score/prompt-short.txt

I have uploaded my test data into a variety of AI systems but have gotten the best results from M365 Copilot Researcher and Analyst:

My original script does the extraction and the uploading for you together, but this new script now allows you to do just the extraction and then take that data and use any AI system or prompt you wish.

I have also created a number of additional scripts that extract as well as analyse a variety of other M365 services such as Exchange, SharePoint Entra Id and more. These are available to CIAOPS Patrons.

If you find a great prompt to use with this extracted data, let me know and I’ll share it so everyone can benefit.

Combining PowerShell and AI for M365 Security Analysis

I’ve used AI to create smart Microsoft 365 expert technical agents which I have deployed to Teams for CIAOPS Patrons:

I’ve also created a smart Microsoft 365 expert technical agent that you can use for free via email:

https://blog.ciaops.com/2025/06/11/get-your-m365-questions-answered-via-email-2/

simply by putting your question in the body of an email and sending it to robert.agent@ciaops365.com.

Now, I have integrated AI into my PowerShell scripts! Let me explain what I’ve done.

I’ve created an agent in Azure AI Foundry that is ‘grounded’ with all my M365 knowledge that is in the CIAOPS Patron community. I’ll cover off what I have learned about Azure AI Foundry in another post.

Next, I created a PowerShell script that firstly logs into a tenant to be inspected,

extracts all the security information like Secure Score details, Conditional Access policies and more,

bundles all that up into a single JSON file (about 8MB in size)

and then connects to my Foundry agent and uploads that extracted data for analysis

After analysis it generates and displays an extensive HTML report

which looks like:

and you can find a complete copy of to review at here, because it is too large for this post:

https://github.com/directorcia/Office365/blob/master/Analysis/secure-score-foundry.png

I’ve configured my Foundry agent to use a ‘Model router’, meaning that the agent uses what it things is the best LLM to do the analysis automatically.

The report include Prioritized recommendations:

A visualized Remediation Roadmap:

and whole lot more. I encourage you to take a moment and study the example output for yourself, which is AI generated.

I am now building similar AI analysis scripts for al M365 services like Exchange, SharePoint, etc and plant expand these over time.

Here’s the best part. As part of my testing process I am happy to make this Secure Score AI Analysis script available to a select few who read this and send me an email (director@ciaops.com) asking for a copy. You’ll need to be comfortable with PowerShell and have the MSGraph module already installed to run the script. Even better for the select few that do respond – I’ll give you access to my Azure AI Foundry agent for FREE to do the analysis. There are some conditions you’ll need to agree to, like going on my email list and understanding this is all still a beta test but there will be no cost if you qualify and agree. To start that process just email me (director@ciaops.com) saying you are keen to give it a go and I’ll send along the all the details.

There are just so many ways that I can see how to integrate AI with PowerShell and I’ll be sharing more soon on what I am doing.

New publication–Ongoing AI support & Optimization Playbook for MSPs

https://directorcia.gumroad.com/l/aisupportmsp

Ongoing AI Support & Optimization Playbook (Managed AI Services for SMB MSPs)

Introducing the Ongoing AI Support & Optimization Playbook – your ultimate guide to mastering managed AI services for SMB MSPs! This comprehensive playbook is designed to empower Managed Service Providers (MSPs) with the knowledge and tools needed to deliver continuous AI support and optimization after deploying Microsoft 365 Copilot.

Why Read This Playbook?

Step-by-Step Guidance: This playbook offers a detailed, step-by-step guide for MSPs to ensure that AI solutions remain effective and aligned with client needs. It covers everything from technical operations to business practices, making it an invaluable resource for maintaining and enhancing AI capabilities.
Proactive Maintenance: Learn how to proactively monitor and improve AI solutions. The playbook provides insights on leveraging Microsoft’s admin tools to track user interactions, measure impact, and gather feedback. This ensures that AI tools like Copilot are always optimized and delivering value.
Business Value Delivery: Discover how to position yourself as a long-term AI partner for your clients. The playbook emphasizes the importance of engaging with stakeholders, demonstrating value, and identifying growth opportunities. This approach helps MSPs build strong, lasting relationships with their clients.
Packaging and Pricing: Get practical advice on how to package, price, and integrate AI services into your existing offerings. The playbook includes best practices for defining service scope, setting clear expectations, and choosing the right pricing model to ensure profitability.
Real-World Examples: Benefit from real-world examples and case studies that illustrate the successful implementation of AI support and optimization strategies. These examples provide valuable insights and inspiration for applying the playbook’s principles in your own business.

Key Benefits

Continuous Optimization: Ensure that AI tools like Microsoft 365 Copilot remain effective and up-to-date, providing ongoing value to your clients.
Enhanced Client Relationships: Position yourself as a strategic AI partner, not just a technician, by delivering continuous improvement and innovation.
Increased Revenue: Identify upsell and expansion opportunities to grow your recurring revenue through managed AI services.
Comprehensive Support: Offer a clear support channel for AI-related issues, ensuring that your clients receive timely and effective assistance.

The Ongoing AI Support & Optimization Playbook is a must-read for any MSP looking to excel in the rapidly evolving AI landscape. By following the guidance provided, you can transform a one-time AI deployment into a long-term, profitable service that continuously delivers value to your clients 1.

Don’t miss out on this essential resource – get your copy today and take your AI support services to the next level!

Now included with MSP AI Playbook bundle – https://directorcia.gumroad.com/l/mspaipb

See all the titles available at – https://directorcia.gumroad.com/

CIA Brief 20260118

Demystifying Exchange Online Mailbox Quotas –

https://techcommunity.microsoft.com/blog/exchange/demystifying-exchange-online-mailbox-quotas/44864…

Inside RedVDS: How a single virtual desktop provider fueled worldwide cybercriminal operations –

https://www.microsoft.com/en-us/security/blog/2026/01/14/inside-redvds-how-a-single-virtual-desktop-provider-fueled-worldwide-cybercriminal-operations/

Turn Complexity into Clarity: Introducing the New UEBA Behaviors Layer in Microsoft Sentinel –

https://techcommunity.microsoft.com/blog/microsoftsentinelblog/turn-complexity-into-clarity-introdu…

After hours

The AI coding boom hits software – https://www.youtube.com/watch?v=FkmuyUTZvXU

Editorial

If you want to be part of a dedicated Microsoft Cloud community with information and interactions daily, then consider becoming a CIAOPS Patron – www.ciaopspatron.com.

Watch out for the next CIA Brief next week