Always On VPN vs. Entra Private Access: Choosing the Right Access Model for Your Organization

The predominant solution for secure remote access today in the Microsoft ecosystem is Always On VPN. Always On VPN is based on traditional Virtual Private Network (VPN) technology originally developed in the mid-1990s. However, Microsoft recently introduced Entra Private Access, which is part of the Global Secure Access (GSA) Security Service Edge (SSE). Entra Private Access is an identity-centric Zero Trust Network Access (ZTNA) solution designed to replace traditional VPN solutions. It offers significantly improved security with granular resource access without dependency on on-premises infrastructure. This article outlines where each solution fits best and how organizations can transition safely between them.

Always On VPN

First introduced in Windows 8, Microsoft Always On VPN provides seamless, transparent, secure remote access using client-based VPN protocols such as Internet Key Exchange version 2 (IKEv2) and Secure Socket Tunneling Protocol (SSTP). When establishing a VPN connection, a virtual network adapter is created, and an IP address is assigned to the interface to facilitate tunneled network communication with the internal network.

Architecture

Always On VPN requires substantial on-premises supporting infrastructure. In addition to the VPN servers themselves, administrators must also deploy authentication servers (RADIUS or NPS) and certificate services (AD CS). Administrators must manage public TLS certificates for SSTP connections. Also, larger deployments may require on-premises load balancers and/or cloud-based Global Server Load Balancing (GSLB) solutions. Further, additional configuration is needed to integrate Entra ID Conditional Access. Because this infrastructure must be publicly accessible by design, it becomes an attractive target for attackers. In addition, the complex infrastructure has many interdependencies, resulting in significant administrative overhead for network and security administrators.

Access Model

Most commonly, Always On VPN provides full network access to the internal network. Full network access is accomplished by configuring IP routing on the client to ensure internal client network subnets are routed over the VPN tunnel. In this model, clients are often implicitly trusted once connected. Once authenticated and authorized, users receive full, unfettered access to the internal network across all protocols and ports. This level of access introduces a significant security risk and does not adhere to modern zero-trust network access models. To address this, administrators must implement additional security controls internally (perimeter or DMZ firewalls) to restrict network access for Always On VPN clients.

Zero Trust Always On VPN?

Always On VPN includes support for traffic filters that can restrict network access and provide zero-trust-like access. However, these controls exist only on the client side, so an attacker with administrative access to the endpoint can easily bypass them. They should not be considered a reliable way to enforce zero trust for Always On VPN connections.

Entra Private Access

Entra Private Access is part of Microsoft’s Global Secure Access (GSA) Security Service Edge (SSE). It is a robust, cloud-based zero-trust network access (ZTNA) service that provides granular access to on-premises resources. It requires installing a client-side agent and one or more Private Network connectors on-premises to facilitate remote network access. Entra Private Access deeply integrates with Entra ID, so you can easily configure Conditional Access policies for any published resource, including multifactor authentication for legacy protocols such as SSH.

Limited Network Access

Unlike legacy VPNs, GSA does not create a virtual network interface when establishing a connection. Instead, GSA operates as a filter driver deep in the Windows networking stack, intercepting and rerouting network traffic bound for the internal network. The GSA client eliminates the complexities of IP address management, network routing, and firewalling. In addition, authentication and authorization are handled natively by Entra ID and Conditional Access.

Minimal Infrastructure

Entra Private Access is a cloud-based service with minimal on-premises supporting infrastructure requirements. Administrators must only deploy the Entra Private Network connector on one or more on-premises servers to facilitate remote access for Global Secure Access clients. The Entra Private Network is a lightweight software agent that requires little to no post-deployment support. The administrative burden is much lighter compared to Always On VPN.

Key Differences at a Glance

The table below highlights the most important architectural, security, and operational differences to help determine which solution best fits your environment.

AspectAlways On VPNEntra Private Access
ArchitectureOn-premises VPN gateway(s)Cloud-based service
Access ModelFull network access via a routable IP address assigned to the endpointPer-resource zero-trust network access (ZTNA); no full network access
AuthenticationOn-premises AD or Entra ID (AD-synced accounts only)Entra ID (AD-synced or cloud-native)
Client SoftwareBuilt-in or third-partyGlobal Secure Access client
Tunneling ProtocolsIKEv2, SSTPgRPC
Network ExposureMust expose VPN servers to the public InternetNone. Private Network Connectors require outbound access only
GranularityAll protocols and ports (default)Application-level (FQDN, IP/port, IP range, CIDR blocks)
Conditional AccessRequires additional configurationNative per-app enforcement
Device-Based ConnectivityYes – device tunnel provides pre-logon connectivityNone
Infrastructure RequirementsVPN servers, RADIUS servers, internal PKI, AD, load balancers, GSLBEntra Private Network connector (minimum one server, two recommended for redundancy)
Device SupportWindows onlyCross-platform (Windows, macOS, iOS, Android)
LicensingIncluded in OS licenseAdditional per-user costs with Entra Suite or standalone Entra Private Access license

Advantages of Always On VPN for Domain-Joined Endpoints

Always On VPN integrates more naturally with classic Active Directory domain-joined Windows devices. Always On VPN includes features that Entra Private Access does not currently provide, which administrators may require to provide full support for their mobile devices.

Device Tunnel Support

The Always On VPN device tunnel provides machine-based pre-logon connectivity. The device tunnel ensures access to on-premises authentication services (domain controllers) before the user logs on to the endpoint. The device tunnel allows for logging in without cached credentials (e.g., for new users) and streamlines password changes. In addition, it ensures network access to support complete group policy processing for remote users. Entra Private Access is user-based only and does not include device-based connectivity. The device tunnel is one of the most significant functional gaps between Always On VPN and Entra Private Access.

Note: Although device-based connections are not currently available in Entra Private Access at the time of this writing, Microsoft may add the feature in the future.

Windows Native Integration

Always On VPN leverages the built-in Windows VPN client, which integrates deeply with the operating system. The Windows VPN client is mature and robust, supporting secure authentication protocols with certificates or smart cards. Always On VPN requires no additional client software. For Entra Private Access, administrators must deploy and manage a separate software component, the Global Secure Access client.

Full Network Access

The domain is a trust boundary, and domain-joined endpoints require broad network access to function. For example, domain-joined endpoints must have access to domain controllers, and most access those resources using several protocols and numerous different ports. In addition, these endpoints must be able to connect to a variety of other internal resources, such as DNS servers, certification authorities (CAs), revocation servers (HTTP, OCSP, LDAP), systems management servers, file shares, printers, and more. Furthermore, much of this access occurs via Remote Procedure Call (RPC) and Distributed COM (DCOM), which use ephemeral (dynamic) port ranges (49152-65535). Enforcing firewall policy to restrict access for remote domain-joined clients is challenging because these endpoints require significant resources.

So, if your managed endpoints are primarily domain-joined and depend on pre-logon network connectivity, Always On VPN remains the more mature and feature-complete choice today.

Why Entra Private Access is Ideal for Native Entra ID Joined Devices

Entra Private Access is designed around a cloud-first, identity-centric Zero Trust model and has explicit client and device requirements that align best with Entra ID joined devices.

Client Requirements

The Global Secure Access client required for Entra Private Access requires Windows devices to be Microsoft Entra-joined or Microsoft Entra hybrid-joined. Domain-joined only (non-hybrid) devices are not supported. Unlike the native VPN client built into Windows, the Global Secure Access client is a separate piece of software that administrators must install independently.

Per-App Zero Trust

Entra Private Access controls access using FQDNs or IPs (individual, ranges, or networks) and specific protocol/port combinations instead of full network routing. Per-app access aligns with the modern cloud-native device model by avoiding broad network exposure and evaluating every access request through Conditional Access (including device compliance, MFA for legacy protocols, and more). Unlike Always On VPN, the principle of least privilege is enforced at all times.

Simplified Management

Entra Private Access requires minimal on-premises supporting infrastructure. There’s no need for VPN servers, RADIUS servers, or complicated certificate services for VPN authentication. Entra Private Access natively uses Entra ID and Conditional Access, eliminating the need for certificate authentication.

Cross Platform

Entra Private Access provides cross-platform support. Not only does it support Windows clients (Enterprise or Professional editions), but it also supports macOS, iOS, and Android. Broad client support makes Entra Private Access a comprehensive, secure remote access solution for all your managed endpoints.

In summary, Entra Private Access provides a cleaner, more secure, and lower-management experience for organizations moving toward Entra ID joined device fleets, especially when combined with Microsoft Intune for management and Conditional Access policies for enhanced security.

Licensing

Always On VPN and Entra Private Access use different licensing models.

Always On VPN

No per-user or per-device licensing required for Always On VPN. Always On VPN licensing is included with the Windows operating system license you already own.

Entra Private Access

Entra Private Access requires a separate license and incurs an additional per-user cost. It is included with the Microsoft Entra Suite license (~$12.00/user/month), or as a separate, standalone Entra Private Access license (~$5.00/user/month). You can learn more about Microsoft Entra licensing here.

Migration Path

Migrating from Always On VPN to Entra Private Access is low-risk. Using a phased approach, administrators can move from Always On VPN to Entra Private Access with minimal disruption. Start by planning for Entra Private Access (client agent deployment, connector placement, conditional access policies, etc.), then gradually deploy the solution, initially coexisting with Always On VPN but moving toward full deployment. Once complete, decommission the legacy VPN. Key steps include:

  1. Assess your resources, devices, and Entra ID licensing.
  2. Enable Entra Private Access, deploy one or two Private Network Connectors on-premises, and install the Global Secure Access client on devices.
  3. Configure access rules. Begin with Quick Access to replicate VPN-like behavior.
  4. Run both solutions side-by-side. Pilot with a small group, migrate apps/users incrementally, and enforce Conditional Access (including MFA for sensitive applications).
  5. Phase out and decommission Always On VPN once stable.

This approach reduces infrastructure overhead, delivers granular zero trust security, and aligns with a cloud-first identity strategy.

Summary

Microsoft Always On VPN provides reliable on-premises remote access for Windows devices using protocols such as IKEv2 and SSTP. Today, it remains the best choice for environments that use traditional Active Directory domain-joined devices, where pre-logon connectivity and broad network access are required. However, Always On VPN requires heavy infrastructure and typically grants risky full network access.

Entra Private Access is the preferred solution for organizations adopting a cloud-first, Zero Trust strategy with Entra ID joined endpoints. Its per-application access model, native Conditional Access enforcement, reduced infrastructure footprint, and cross-platform support make it ideal for modern managed endpoints where least-privilege access and simplified operations are priorities.

In practice, many organizations will benefit from running both solutions in parallel during a transition period, using Always On VPN to support domain-joined endpoints and Entra Private Access for modern, Entra-joined devices. Over time, as device fleets and applications modernize, Entra Private Access can progressively replace legacy VPN infrastructure while improving security posture and reducing operational complexity.

Ready to Modernize Your Remote Access Strategy?

Schedule a free one-hour consultation to review your current Always On VPN deployment, assess readiness for Entra Private Access, and identify a secure, practical migration path tailored to your environment. We’ll cover architecture considerations, device requirements, licensing implications, and common pitfalls—no obligation required. Fill out the form below to request more information and schedule your free consultation.

Additional Information

Microsoft Entra Private Access Intelligent Local Access (ILA)

Preventing Port Exhaustion on Entra Private Network Connector Servers

Microsoft Security Service Edge (SSE) Now Generally Available

Microsoft Entra Security Service Edge (SSE) on RunAs Radio

Always On VPN SSTP and 47-Day TLS Certificates

The Secure Socket Tunneling Protocol (SSTP) VPN protocol uses Transport Layer Security (TLS) encryption and HTTP transport over TCP port 443. SSTP is easy to configure and firewall-friendly, making it an excellent choice for the Always On VPN user tunnel. Security best practices dictate using a TLS certificate issued by a public Certification Authority (CA). Today, the maximum lifetime of a public TLS certificate is 398 days (approximately 1 year). Always On VPN administrators using SSTP are familiar with the process of renewing their SSTP certificate annually. However, that’s about to change.

47 Days

In April of this year, the CA/Browser Forum, a voluntary consortium of public CAs, browser vendors, and other industry stakeholders that develop and promote security standards and best practices for digital certificates and Public Key Infrastructure (PKI), adopted a measure reducing the current maximum lifetime of public TLS certificates to 47 days. This means Always On VPN administrators using public TLS certificates must eventually update their TLS certificates monthly.

Automation

Of course, no administrator in their right mind would want to renew SSTP certificates every month. Automating this process will be crucial to ensuring reliability and reducing management overhead. I’ll provide more details later in this post.

Why Is This Happening?

The industry has been trending toward shorter certificate lifetimes for a while now. In the old days, you could purchase a certificate valid for 5 years or more. Today, a one-year certificate is all you can get. Let’s Encrypt, a public CA that issues certificates for free, issues only 90-day lifetime certificates.

Advantages

The advantage of using short-lived certificates for public TLS certificates is that they improve security and provide agility for future changes. Public TLS certificates become less secure and trustworthy over time. The longer a certificate is valid, the less trustworthy it becomes and the longer the opportunity for an attacker to leverage a certificate for which the private key has been compromised.

Why 47 Days?

A 47-day maximum certificate lifetime allows administrators to rotate their certificates monthly (a maximum of 31 days plus some margin to resolve issues).

Not So Fast

The good news for Always On VPN administrators using SSTP with public TLS certificates is that they won’t have to worry about this immediately. The reduction in maximum certificate lifetime to 47 days takes place gradually over a few years.

  • Today, the maximum public TLS certificate lifetime is 398 days
  • On March 15, 2026, the maximum public TLS certificate lifetime will be reduced to 200 days
  • On March 15, 2027, the maximum public TLS certificate lifetime will be reduced to 100 days
  • On March 15, 2029, the maximum public TLS certificate lifetime will be reduced to 47 days

Let’s Encrypt

Over the years, I’ve deployed Always On VPN with SSTP for several customers using Let’s Encrypt TLS certificates. Let’s Encrypt is a pubic CA that issues certificates with a maximum lifetime of 90 days, so automating this task is essential. Let’s Encrypt supports ACME, a standard protocol for automating the issuance and renewal of TLS certificates, which makes automating TLS certificate installation and renewal a breeze.

Sample Script

I’ve published a sample PowerShell script demonstrating how to automate the enrollment process for Let’s Encrypt TLS certificates. It leverages the Posh-ACME PowerShell module and my AOVPNTools module to enroll and automatically install a TLS certificate for SSTP. This script will also work for DirectAccess. You can find the sample script here.

Note: My sample script demonstrates using the Cloudflare DNS plugin for Posh-ACME. Posh-ACME has plugins for many public DNS providers, which can be found here. Feel free to customize my script to meet your specific needs.

Act Now

Always On VPN administrators are advised to consider solutions to automate TLS certificate enrollment and renewal as soon as possible. If your public CA of choice doesn’t support some form of certificate automation like ACME, it’s time to find another provider.

Summary

Starting in March 2026, the maximum lifetime for public TLS certificates will be reduced gradually, reaching just 47 days by March 2029. Automation will no longer be optional for Always On VPN administrators using SSTP—it will be essential. Tools like the Posh-ACME PowerShell module provide a reliable solution to streamline certificate management and ensure uninterrupted connectivity. Now is the time to prepare for this industry shift by implementing automated certificate renewal solutions. If you’d like professional assistance with this task or simply want to learn more about your options, drop me a note via the contact page, and I’ll respond with more information.

Additional Information

TLS Certificate Lifetimes Will Officially Reduce to 47 Days – DigiCert

Posh-ACME PowerShell Module

Posh-ACME Documentation

Always On VPN Tools (AOVPNTools) PowerShell Module

What’s New in Always On VPN DPC 4.3.1

The latest release of PowerON Platforms’ Always On VPN Dynamic Profile Configurator (DPC), version 4.3.1, is now available for download. This recent update includes fixes for previously known issues. In addition, it contains some critical new features administrators will find helpful in addressing the challenges they face with Always On VPN client configuration.

What Is DPC?

Always On VPN DPC is a solution to manage Always On VPN client configuration settings. It was originally designed to be used with on-premises Active Directory but can also be deployed with Microsoft Intune. DPC streamlines the configuration and management of client settings and includes many advanced features to fine-tune and optimize Always On VPN.

What’s New in 4.3.1

The following essential features are new in the 4.3.1 release of DPC.

Add Device Tunnel Routes to User Tunnel

Always On VPN administrators can now configure DPC to add device tunnel routes to the user tunnel automatically. This configuration option ensures that all traffic flows of the user tunnel when both user and device tunnels are established.

Note: This feature also requires administrators to define route metric options in DPC. Ensure the user tunnel route metrics are set to a lower value than the device tunnel metrics for proper operation.

Restart RasMan

Always On VPN connections occasionally fail with error 602 (ERROR_PORT_ALREADY_OPEN). The workaround for this is to restart the RasMan service on the endpoint. DPC now supports automatically restarting the RasMan service when this error occurs, ensuring reliable operation for Always On VPN connections.

Machine Certificate Filtering

DPC 4.3.1 now includes a feature to allow administrators to enable machine certificate filtering for Always On VPN device tunnels. This addresses a challenge when the endpoint has multiple machine certificates in its local computer certificate store when the VPN server is configured to accept a certificate with a specific custom application policy (EKU).

Additional Features

In addition, the updated DPC agent core service now run as x64 processes. Also, DPC now supports VPN server FQDNs longer than 63 characters (good news for those using DPC with Azure VPN gateway!).

Download DPC

For those customers currently licensed for Always On VPN DPC you can download the latest release here.

https://support.poweronplatforms.com/support/solutions/articles/8000066807

Not using DPC?

If you’re not using DPC, you are missing out! You can learn more about DPC and register for a free evaluation by visiting the link below.

https://aovpndpc.com

Optionally, you can fill out the form below and I’ll provide you with more information.

Additional Information

PowerON Platforms’ Always On VPN Dynamic Profile Configurator (DPC)

Always On VPN DPC Advanced Features

Always On VPN DPC with Microsoft Intune