RunAs Radio

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 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