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The Content Management System Landscape with Matt Garrepy Aug 12, 2026

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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!

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Recorded July 6, 2026

Ransomware Readiness with Heather Renze Aug 05, 2026

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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!

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Ransomware Guidance from NIST

Recorded June 25, 2026

Azure Virtual Desktop Hybrid with Travis Roberts Jul 29, 2026

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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!

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Recorded June 22, 2026

Security Begins at Procurement with Jessie Schofer Jul 22, 2026

Show notes

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?

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Recorded June 23, 2026

Finding Security Vulnerabilities using AI with Sami Laiho Jul 15, 2026

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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.

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Recorded June 19, 2026

Implementing Azure Policies with Barbara Forbes Jul 08, 2026

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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!

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Recorded May 12, 2026

AI-Accelerated Supply Chain Attacks with Mackenzie Jackson Jul 01, 2026

Show notes

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!

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Recorded June 15, 2026

Securing Developers with Tanya Janca Jun 24, 2026

Show notes

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!

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Recorded May 8, 2026

47 Day Certificates with Todd Gardner Jun 17, 2026

Show notes

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!

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Recorded May 8, 2026

How Machine Learning Fails with Megan Robertson Jun 10, 2026

Show notes

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!

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Recorded May 7, 2026

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