RunAs Radio

How secure are your PowerShell scripts? Richard talks to Mike O'Neill about the powerful security features introduced with PowerShell 7.3 and above, including session configuration files and clean blocks. Mike talks about how some organizations are strict about installing anything on servers, including the latest version of PowerShell - which is one of the reasons 5.1 has persisted so long. But that ends with 26H2 and opens the door to securing your PowerShell with strict controls over accounts, cmdlets, and more! The latest PowerShell makes it easier to have just enough administration - and makes it harder for the black hats to exploit! Links PowerShell 7 Just Enough Administration New-PSSessionConfiguration File PowerShell Clean Block Monthly PowerShell Team Call Mike's Exchange Add-In for PowerShell Recorded July 9, 2026

What if Microsoft Defender not only detected attackers - but also fought back? Richard talks to Liz Tesch about Microsoft Defender Automatic Attack Disruption and Predictive Shielding. Liz talks about how attacks are often detected before the payload executes, but by the time humans can respond, far more damage has been done. Automatic Attack Disruption acts immediately on detection to limit the attacker by locking accounts, restricting access on a compromised server, and more. Predictive Shielding goes a step further by limiting attackers' ability to respond to the disruption by turning off GPO changes, disabling safe mode, and otherwise interfering with the typical actions that attackers take once they know they have been detected. Add AI to the mix, and everything gets more complicated. The black hats are using AI to attack, and Microsoft Defender XDR is using it to defend - the race is on! Links Microsoft Defender XDR Automatic Attack Disruption Predictive Shielding Microsoft Sentinel Microsoft Defender for Identity Automatic Attack Disruption EBook Web Scale Graph Mining for Cyber Threat Intelligence Research Paper Local AI Agent Discovery with MDE Threat Hunting in Microsoft Sentinel Microsoft Defender for XDR Preview New Features for MDE Recorded June 29, 2026

What is the state of content management systems today? Richard chats with Matthew Garrepy of CMS Critic about his views on how the CMS market continues to evolve. Matt digs into the build-vs-buy conversation that has been going on since the web first emerged - now made more complex with the power of the large language model to generate code. The evolution toward headless CMS brings up the idea of the explosion of different places that a CMS needs to touch now - not just web pages. The landscape for CMS is only getting more complex, and the tooling reflects that! Links CMSCritic Sanity CMS Sitecore EmDash Recorded July 6, 2026

The risk of ransomware is real - are you ready? Richard talks with Heather Renze about her experiences dealing with a ransomware attack and how to get prepared when it happens to you. Heather talks about how ransomware has evolved into a business that has operators, affiliates, and even tech support. Making a plan is essential - involving finance, legal, and IT. Cyberinsurance plays a big role, as do regulatory bodies - it depends on the business you're in. But your plan needs to know three essential things: what breaks first, how long your company can function with it broken, and who can decide on what to do next in the first hour of the event. The plan may or may not work perfectly, but not having a plan is far worse. Get ready! Links Ransomware Guidance from NIST Recorded June 25, 2026

More ways to use Azure Virtual Desktop! Richard chats with Travis Roberts about how Azure Virtual Desktop continues to evolve and provides more options for remote users. Travis talks about how AVD grew out of Terminal Services and so is still very much an IaaS offering - as opposed to Windows 365, which is more PaaS, with less flexibility, but easier deployment. But when you need control, AVD is the way to go, and today will operate in Azure, on-premises via Azure Local. And if you've got an existing virtual desktop infrastructure, AVD Hybrid opens the door to running in a hybrid environment across on-prem and cloud, or to providing a smooth migration path. Lots of choices! Links Terminal Services Windows 365 Windows 365 Flex Azure Virtual Desktop Windows Enterprise Multi-Session FSLogix Azure Local Azure Virtual Desktop on Azure Local Azure Virtual Desktop Hybrid AVD Personal Desktop Assignment Recorded June 22, 2026

Bringing new software or SaaS into your organization is a security risk - how do you assess it? Richard chats with Jessie Schofer about her experiences in HR software acquisition, which led to the creation of secureless.ai. Jessie tells the story of evaluating various SaaS and other software products and realizing that, while the website says they are compliant with GDPR and/or SOC 2, are they really? This leads to a conversation about the product procurement process and about actually understanding the security risk you take on every time a new product is added to your organization. At what point does security block an acquisition? And after being acquired, how often do you reassess? Supply chain security hygiene starts at procurement - are you part of the evaluation? Links Secureless.ai GDPR Enforcement Tracker Recorded June 23, 2026

How are large language models changing the way security vulnerabilities are found? Richard chats with Sami Laiho about the rapidly changing landscape in security exploits. Certain LLM models like Anthropic's Mythos and Microsoft MDASH are optimized to find software vulnerabilities - and potentially fix them. And so there is an arms race of sorts, repairing old vulnerabilities before LLMs in the hands of black hats can exploit them. But what about everyone else? Sami talks about getting LLMs working for your organization to test for potential security risks and assess the impact of new vulnerabilities as they appear. Links Palo Alto Networks Claude Mythos Microsoft MDASH Zero Day Clock Security Update Guide Recorded June 19, 2026

How can Azure Policies help you? While at Techorama in Belgium, Richard sat down with Barbara Forbes to discuss how Azure Policies have evolved and the techniques sysadmins are using to improve security, cost controls, efficiency, and more. Barbara talks about how the default policies are designed to get folks started in Azure quickly - not necessarily optimally. And there are plenty of policy templates out there, but before you implement them, it's worthwhile to review each policy and ask the question "why?" Keeping good documentation on policies makes it easier to know intent, especially when it comes to changing them - and you'll need to change them! There are a number of ways to apply policies, but in the end, they are just more Infrastructure-as-Code, and so easily repeatable. Azure Policies are there to help you provide freedom with guardrails if you implement them carefully! Links Azure Policy Microsoft Cloud Security Benchmark Azure Management Groups Azure Bicep Terraform on Azure Recorded May 12, 2026

How are supply-chain attacks evolving? Richard chats with Mackenzie Jackson about his work helping companies protect their software supply chains from malware attacks. Mackenzie discusses the vulnerability of developers to attacks, since their accounts are often highly privileged and invariably contain access to exploitable secrets. The conversation digs into the challenges of securing various code distribution mechanisms like npm and how you can protect your organization - starting with, don't install packages as soon as they are released! There are effective tools for detecting malware in code, but they take time. Waiting 48 hours can eliminate a lot of risk! Links Aikido Software Trivy Claude Mythos OpenClaw Shai-Hulud Guidance ClawHub Open Source Malware Windows Update Management Recorded June 15, 2026

How can sysadmins help software developers work securely and make more secure applications? While at NDC in Toronto, Richard sat down with Tanya Janca of SheCodesPurple to discuss what admins can do to help address the security challenges software developers face. Tanya talks about securing development environment and pipelines - developers routinely work from high privilege accounts because their tools require it, and as a result, have become the targets of black hats to get access to accounts, keys, and other exploitable resources. There are plenty of tools available to help work through the issues, including the latest AI-powered tools. LLMs can also help generate more secure code in the first place, and Tanya has created a set of prompts you can use to create more secure software. The threat landscape is shifting with these tools, and we need to act quickly to resist the new attacks! Links SheHacksPurple Canadian Guidance on Resisting Supply Chain Attacks OWASP Top 10 Security Risks for 2025 Prompts for Generating Secure Code Recorded May 8, 2026

The 47-day certificate is coming! While at NDC in Toronto, Richard received an update from Todd Gardner about his show last year: certificate authorities are moving toward SSL certificates that last only 47 days! Todd talks about the first decrease in duration that has already passed - as of March 2026, the longest duration certificate you can buy from certificate authorities is 200 days. At the core of these changes is the problem that certificate revocation just isn't working properly, so a short certificate lifespan is the effective solution. Short certificate lifespans make automation to replace certificates essential - and that's where CertKit and other tools come in! Links Lets Encrypt ACME Client Implementations CertKit Apple's 398 Day Rule Microsoft SHA-1 Retirement Google Transparency Logs Perfect Forward Secrecy Recorded May 8, 2026

What can go wrong with machine learning? While at NDC in Toronto, Richard chatted with Megan Robertson about her experience with machine learning projects, often using retail datasets, and where they can go wrong. Megan talks about getting clear expectations and metrics for projects, so you know when you succeed, but then digs into the specifics of problems in machine learning, such as overfitting on test data. Your results are only as good as the data you put in, so a lot of focus goes into building good sets, carefully developing the model with those sets, and using techniques like cross-validation to ensure the model is behaving appropriately. There's a lot that can go wrong, but the results with an effective model can be very powerful - it is worth the effort! Links Cross Validate Model Megan's Website Recorded May 7, 2026

How do you intelligently surface access to your database? While at NDC Toronto, Richard spoke with Jerry Nixon about Data API Builder, Microsoft's tool that enables data professionals using Microsoft databases, including SQL Server, Postgres, CosmosDB, and MySQL, to provide an API layer with security, schema extraction, and governance policies. You can expose the API as a REST interface, a GraphQL interface, and an MCP server! This is a powerful tool for providing controlled access to data while still allowing for ad-hoc access. The potential is huge - you need to check it out! Links Data API Builder GraphQL Recorded May 7, 2026

How can Microsoft Loop make your team more productive? Richard chats with Karinne Bessette about the role that Loop components can play in making meetings where the agenda is live, generating work items in Microsoft Planner, and keeping key information up to date. Karinne talks about how Loop components can be connected to any M365 document, including Outlook, Word, Excel, and OneNote, but only for members of the M365 tenant. Loop is a powerful tool for productivity within the organization! Links Microsoft Loop Microsoft Planner Microsoft OneNote Power Automate Loop Components in OneNote Teams Polls Polls in Loop Loop Admin Policies Recorded April 27, 2026

The original Secure Boot certificate expires in June 2026! Richard talks to Richard Hicks about how Secure Boot works and how the expiration of the master certificate can leave PCs vulnerable to boot-related malware, such as rootkits. Richard discusses recent Microsoft communications on SecureBoot and how to check which certificate your machines have. Workstations using managed updates are likely already up to date, but servers are a different issue. When the certificate expires, you'll no longer receive updates to Secure Boot for known exploits, leaving your machines vulnerable. Update today! Links Secure Boot Certificates Expiring Sony Rootkit Scandal Secure Boot Playbook for Windows Client Windows Update Management Registry Key Updates for Secure Boot Richard's Blog Post on Secure Boot EUFI Certificates Expiring Get-UEFICertificate in PowerShell Gallery Recorded March 9, 2026

What does a production-grade large language model look like? While at NDC Sydney, Richard talked with Vaishnavi Gudur from Microsoft about her work scaling LLMs for Teams transcriptions, summaries, and more! Vaishnavi discusses the underlying complexities of operating the Teams LLM infrastructure for a large array of customers across different countries and regulatory regimes. Data sovereignty also plays a large role: different countries have specific rules on where data must reside and how it can be accessed. As the scale increases and the tail gets longer, the rules set gets more complex! Lots of great thinking about what LLMs look like in a production environment. Links Transcripts in Microsoft Teams Recorded April 24, 2026

How secure is your Active Directory infrastructure? While at Zero Trust World in Orlando, Richard chatted with Spencer Alessi about his work helping companies secure Active Directory, making it more difficult for black hats to exploit it for lateral moves during a breach attempt. Spencer talks about the increasing speed of these exploits, making it much harder to block them after the fact, so it's best to make AD too difficult to target. Jake Hildreth's Locksmith tools are a great place to start - free and open source. There are also Microsoft tools and Spencer's own AD Security Resource Kit to help evaluate your AD infrastructure and lock it down! Links Locksmith Enhanced Security Admin Environment Active Directory Security Resource Kit Recorded March 4, 2026

There's competition in the Office productivity space! Richard chats with Sharon Weaver about her experiences with M365 Copilot and Anthropic's Claude Cowork to improve information worker productivity. Sharon talks about the confusion around all the different copilots in the Microsoft space - including the chat tools, research agents, and more. But when it comes to helping with an Excel spreadsheet, M365 Copilot can't do what Claude Cowork can do. Sharon talks about describing the goals of a spreadsheet to Claude Cowork and having the tool generate the spreadsheet, make corrections, and add formatting. Cowork has similar capabilities for presentations, and with the Connector library, new functionality is being added routinely. There's some competition in the AI productivity space - things are getting interesting! Links Microsoft 365 Copilot Researcher in Microsoft 365 Copilot Claude Cowork Claude Cowork Connectors Copilot in PowerPoint Recorded February 24, 2026

What does the world look like after Microsoft Deployment Toolkit? Richard talks to MDT creator Michael Niehaus about the life and death of MDT. Michael talks about his early days at Microsoft, when he created a better way to manage operating system images so you can build and rebuild Windows PCs for your organization. But MDT had been in maintenance since 2013, without specific support for Windows 11. And now, some security concerns have ended support entirely. So what happens next? Michael offers fixes to keep MDT safe to use, and some alternatives if you want to keep managing your own images! Links Microsoft Deployment Toolkit Michael's Post of the MDT Vulnerability Windows Autopilot Friends of MDT MDT Retirement Notice Microsoft Intune 2Pint DeployR MMS Conference iPXE Anywhere Recorded February 17, 2026

How does your company communicate with its employees today? Richard chats with Emily Mancini about her work with companies that manage internal communications. Emily talks about the power of email, collaborative messaging like Teams, and the Microsoft Viva products Engage and Amplify. The conversation digs into knowing where your people look for info, how they communicate, and what they want to connect with. Being able to measure the response to different communication means helps you to work on better messages and methods - the goal is to enable employees to connect with and utilize the resources of the organization, creating a stronger company culture! Links Microsoft Viva Engage Microsoft Viva Amplify Create and Send a News Digest Recorded March 9, 2026