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 Proxy Server Configuration

Always On VPN Proxy Server Configuration

Web proxy servers are not as common today as they once were, but a few organizations still leverage them to provide secure Internet access for their employees. Commonly they are used to inspect and control Internet traffic and to enforce acceptable use policies. Some organizations may wish to extend this protection to Always On VPN clients in the field by enabling force tunneling. Administrators can define a web proxy server for Always On VPN connections globally for web traffic or individual websites or domains.

VPN Proxy

A VPN web proxy server can be defined when the Always On VPN user tunnel connection uses force tunneling. Although you can still configure a VPN web proxy server with split tunneling enabled, it will not work. It is only functional when force tunneling is in use.

Administrators can configure a VPN web proxy server using the Microsoft Endpoint Manager UI or custom XML deployed with Endpoint Manager or PowerShell. Administrators can define a VPN web proxy server explicitly, or a proxy automatic configuration (PAC) file can be specified.

Note: VPN proxy server settings only work when force tunneling is enabled. Force tunneling is an unsupported configuration for the device tunnel, making the global proxy server setting for the device tunnel unsupported.

Proxy Autoconfiguration

Perform the following steps to configure a VPN web proxy server with a PAC file in Endpoint Manager.

  1. Expand the Proxy section in the Configuration settings of the Always On VPN configuration profile.
  2. Enter the URL for the PAC file in the Automatic configuration script field. Be sure to include the port number in the URL when using a non-standard port.
  3. Leave the Address and Port number fields blank.
  4. Choose Enable or Disable from the Bypass proxy for local addresses drop-down list.

To configure a VPN web proxy server with a PAC file using custom XML, include the following code between the <VPNProfile> and </VPNProfile> tags in the Always On VPN XML configuration file.

Explicit Proxy

Perform the following steps to configure an explicit VPN web proxy server in Endpoint Manager.

  1. Enter the IP address, hostname, or fully qualified domain name (recommended) in the Address field.
  2. Enter the port number in the Port number field.
  3. Choose Enable or Disable from the Bypass proxy for local addresses drop-down list.

To configure an explicit VPN web proxy server using custom XML, include the following code between the <VPNProfile> and </VPNProfile> tags in the Always On VPN XML configuration file.

Namespace Proxy

Administrators can also define VPN web proxy servers on a per-namespace or per-hostname basis. Namespace VPN proxy servers can be helpful for scenarios where routing public websites over the Always On VPN connection is required. Most commonly, this is necessary because the public website restricts access to the IP address of the on-premises Internet gateway.

A namespace VPN proxy server is implemented using a Name Resolution Policy Table (NRPT) rule. At the time of this writing, a bug in Microsoft Endpoint Manager prevents administrators from deploying this option using the UI.

As you can see here, administrators can specify a proxy server as part of an NRPT rule in the Endpoint Manager UI. Notice this section of the UI validates the proxy FQDN correctly.

Always On VPN Proxy Server Configuration

However, when you try to save the configuration profile, Endpoint Manager returns the following error.

“Unable to save due to invalid data. Update your data then try again: ProxyServerUri must be a valid URL or be empty.”

Interestingly, when entering a URL such as http://proxy.lab.richardhicks.net:8080/ in the Proxy field, the Endpoint Manager UI accepts it and successfully validates. But according to the VPNv2 Configuration Service Provider (CSP) reference, the value must be entered as an IP address. A hostname or FQDN also works based on my testing. Entering a URL as shown in the example above will not work at all.

With that, the only way to implement a namespace VPN web proxy server is to use custom XML. To do this, include the following code between the <VPNProfile> and </VPNProfile> tags in the Always On VPN XML configuration file.

Include the leading “.” to specify the entire domain, as shown above. Omit the leading “.” to specify an individual host (for example, app.richardhicks.com). Repeat this section for each additional host or domain, as required.

Caveat

Unfortunately, the Microsoft Internet Explorer web browser is the only browser that functions with the namespace VPN web proxy server. All modern web browsers, including Microsoft Edge, ignore the namespace proxy setting entirely, which seriously limits this feature’s usefulness in most organizations today.

Workaround

If routing a public website over the Always On VPN tunnel is required, adding its IP address(es) to the Always On VPN connection’s routing table is needed. However, doing this presents some unique challenges, as public websites frequently have many IP addresses, which are often dynamically changing. Also, it is common for public websites to pull content from many different domains or use Content Delivery Networks (CDNs), making the problem of identifying which IP addresses to add to the Always On VPN connection’s routing table even more challenging. Further, administrators must update the client configuration each a public website’s IP address changes, adding significant management overhead.

Summary

Routing client Internet traffic through an on-premises web proxy server for Always On VPN clients works well when force tunneling is enabled. Administrators can explicitly define a web proxy server or use a proxy automatic configuration (PAC) file. All web browsers work without issue in this scenario. Using a namespace proxy is only effective when browsing with Microsoft Internet Explorer. All modern web browsers, including Microsoft Edge, ignore namespace proxy settings.

Additional Information

Windows 10 Always On VPN and the Name Resolution Policy Table (NRPT)

Windows 10 VPNv2 Configuration Service Provider (CSP) Reference

Windows 10 Always On VPN Client DNS Server Configuration

Always On VPN LockDown Mode

Always On VPN LockDown ModeWhen an Always On VPN connection is provisioned to a Windows 10 client, there’s nothing to prevent a user from disconnecting or even deleting the connection. Some administrators have expressed concern about this, fearful that users may disable the VPN to improve performance or circumvent access controls when force tunneling is enabled. Also, administrators may wish to prevent users from accidentally or purposefully making changes to the configuration, or even deleting the connection entirely.

LockDown Mode

To address these concerns, Microsoft included a feature called LockDown mode for Always On VPN. Once enabled, the following conditions apply.

  • The LockDown VPN connection is always on.
  • The LockDown VPN connection cannot be disabled.
  • The user can’t make changes to or delete the LockDown connection.
  • No other VPN connections can exist on the client.
  • Force tunneling is enabled by default (split tunneling in LockDown mode is not supported).

Challenges with LockDown Mode

Always On VPN LockDown mode brings with it some unique challenges, however. Consider the following.

Limited Protocol Support

LockDown mode only supports IKEv2 and the native (built-in) VPN client. Third-party plug-in provider clients are not supported. IKEv2 is an excellent VPN protocol in terms of security, but operationally speaking it has some serious drawbacks.

Force Tunneling Only

LockDown mode uses force tunneling exclusively. All network traffic must go over the VPN connection. However, if the VPN connection is not available, the client will be unable to access any network resources at all, local or remote.

Captive Portal Issues

LockDown mode prevents clients from connecting to network resources from a network with a captive portal.

On-premises Connectivity

In LockDown mode all network traffic must flow over the VPN tunnel even if the client is on the internal network. This also means that if the VPN server is not reachable internally (unable to resolve public hostname, protocols/ports blocked by internal firewall, unable to route to VPN server, etc.) the client will not be able to access any internal or external network resources at all.

Deleting a LockDown VPN Connection

Deleting a LockDown VPN connection is also challenging. Administrators will find that trying to delete it using the UI or PowerShell often fails. To delete a LockDown Always On VPN connection, use psexec.exe to open an elevated PowerShell command window running in the system context using the following command.

.\psexec.exe -i -s C:\windows\system32\WindowsPowerShell\v1.0\powershell.exe

In the new elevated PowerShell window run the following commands to delete the LockDown VPN connection.

$ConnectionName = ‘[LockDown VPN connection name]’
$ConnectionNameEscaped = $ConnectionName -replace ‘ ‘, ‘%20’
$CimInstance = Get-CimInstance -Namespace ‘root\cimv2\mdm\dmmap’ -ClassName ‘MDM_VPNv2_01′ -Filter “ParentID=’./Vendor/MSFT/VPNv2′ and InstanceID=’$ConnectionNameEscaped'”
Remove-CimInstance -CimInstance $CimInstance

Optionally, download and run Remove-LockDownVPN.ps1 here.

Summary

While Always On VPN LockDown mode might seem like a good idea initially, its implementation is heavy-handed and practically speaking ends up causing more problems than it solves. For administrators that plan to enable this feature, carefully consider the drawbacks and limitations outlined above and their impact on supportability and the user experience.

Additional Information

Windows Always On VPN Device Tunnel Config using Microsoft Intune

Windows 10 Always On VPN Security Configuration 

Windows 10 Always On VPN Hands-On Training