How to Migrate from Legacy VPNs to Entra Private Access (Real Strategies from a Veteran)

Richard Hicks wrote the book on DirectAccess. Then he wrote the one on Always On VPN. Now he’s here to tell you it’s time to move on from both (and other legacy VPNs). Over the last two years, Richard has helped numerous enterprise customers navigate the shift from legacy VPN to Microsoft Entra Private Access, and he’s collected some hard-learnt lessons along the way that most migration guides won’t tell you.In this episode, Richard - enterprise security consultant and early Entra Private Access insider - breaks down why traditional VPN is fundamentally broken for today’s threat landscape, how Entra Private Access works under the hood, and the exact crawl-walk-run playbook he uses to migrate enterprise customers without disruption. Plus: his hot take on the Microsoft E7 announcement and why it just changed the pricing conversation forever.In this episode you’ll learn:* Why your VPN tunnel is a security liability — and how a single compromised device can expose your entire corporate network* How Entra Private Access works differently to traditional VPN, and why that architectural shift matters for security* The “Quick Access” migration strategy that lets you get off legacy VPN fast, without locking everything down on day one* How to deploy the Global Secure Access client alongside your existing VPN — so you can migrate field-based workers without a single disconnection* What most teams get wrong about the Entra Private Network Connector — and the scaling pitfalls that catch enterprises off guard* Why Conditional Access knowledge, not connectivity, is the real key to a successful zero trust migration* The current limitations of Entra Private Access and how to plan around them* We also discuss the new ‘E7’ which includes Entra Private AccessSubscribe with your favorite podcast player or watch on YouTube 👇About Richard HicksRichard Hicks is the founder and principal consultant at Richard M. Hicks Consulting, Inc. A Microsoft Most Valuable Professional (MVP) with more than 30 years of experience implementing secure remote access and public key infrastructure (PKI) solutions, he is a widely recognized enterprise mobility and security infrastructure expert sought after by organizations worldwide. His mission is to help companies provide visibility, control, and assurance for their field-based users and devices, ensuring the highest level of security and productivity for today’s highly mobile workforce.LinkedIn - https://www.linkedin.com/in/richardhicks/🔗 Related Links* Richard’s Blog - https://directaccess.richardhicks.com/* Richard M. Hicks Consulting, Inc - https://www.richardhicks.com/* https://directaccess.richardhicks.com/always-on-vpn-vs-entra-private-access/📗 Chapters00:00 Intro 01:10 The History of Direct Access and Always On VPN 05:59 Transitioning to Zero Trust and Entra Private Access 11:34 Seamless Side-by-Side VPN Migration 17:37 Using Quick Access to Kickstart Zero Trust 23:43 Changing Mindsets: Identity over IP Addresses 27:55 The New Zero Trust Network Assessment Tool 29:17 Avoiding Pitfalls with the Entra Private Network Connector 33:11 Feature Wishlist: IPv6 and Process Binding 38:46 Hot Takes on the New Entra E7 SuitePodcast Apps🎙️ Entra.Chat - https://entra.chat🎧 Apple Podcast → https://entra.chat/apple📺 YouTube → https://entra.chat/youtube📺 Spotify → https://entra.chat/spotify🎧 Overcast → https://entra.chat/overcast🎧 Pocketcast → https://entra.chat/pocketcast🎧 Others → https://entra.chat/rssMerill’s socials📺 YouTube → youtube.com/@merillx👔 LinkedIn → linkedin.com/in/merill🐤 Twitter → twitter.com/merill🕺 TikTok → tiktok.com/@merillf🦋 Bluesky → bsky.app/profile/merill.net🐘 Mastodon → infosec.exchange/@merill🧵 Threads → threads.net/@merillf🤖 GitHub → github.com/merill Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe