Short answer: the best replacement depends on whether your employees need a whole-network tunnel or access to individual private applications. Microsoft Entra Private Access, Zscaler Private Access, and Cloudflare One are the strongest alternatives when you want identity-based, app-level access across platforms. Keep Azure VPN Gateway when legacy file shares, RDP, management tools, or other workloads still require network-level connectivity. For a Windows-only organization that already has reliable auto-triggered tunnels, Always On VPN remains a valid option rather than a technology that must be replaced automatically.
Start with the access model, not the product name
Windows Always On VPN creates an automatically triggered tunnel from a managed Windows device to a private network. That model is useful when a remote employee must reach many internal subnets, legacy protocols, file servers, or management systems without launching a client manually. It is also familiar to teams that already operate certificates, routing, VPN gateways, and Windows device-management policies.
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Its main limitation is architectural: a network tunnel can expose more reachability than a user needs. A remote worker who only opens one internal web application may receive a path toward an entire subnet unless routing and policy are carefully constrained. Troubleshooting also spans the endpoint, authentication service, gateway, DNS, routes, certificates, and the application itself.
Modern alternatives move the policy decision closer to the application and the user identity. Instead of asking whether a device may join a broad network, they evaluate the user, device posture, multifactor authentication, and requested private application. That can reduce lateral movement and make cross-platform access easier, but it requires a dependable application inventory and connector design.
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Use this rule of thumb:
- Choose app-level zero-trust access when employees need a defined set of private applications, you have a strong identity provider, and you want consistent policy across Windows, macOS, Linux, mobile devices, or BYOD.
- Choose a network-level VPN when applications depend on broad subnet reachability, SMB file shares, RDP, UDP, management protocols, or other traffic that is difficult to publish individually.
- Use a hybrid model when some applications are ready for zero-trust access but others still require a tunnel. Microsoft recommends phased coexistence rather than a “big bang” cutover.
Microsoft’s documentation describes Always On VPN as a platform for “advanced scenarios by integrating Windows operating systems and third-party solutions.” It also documents granular routing policies that can be narrowed to individual applications. Those capabilities mean a carefully designed Always On deployment may solve the security problem without a wholesale migration.
What Always On VPN provides today
Microsoft documents Always On VPN for Windows 10, Windows 11, and Windows Server. It supports domain-joined, workgroup, and Microsoft Entra-joined devices, so an organization is not limited to a traditional Active Directory estate.
Automatic user and device tunnels
A user tunnel starts in the user context, while a device tunnel starts before sign-in and can support device management or pre-logon scenarios. Auto-triggering removes the requirement for an employee to open a VPN application each time they work remotely. The trade-off is that administrators must define trigger, authentication, routing, and certificate behavior precisely.
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Authentication and MFA integration
Always On VPN can integrate with RADIUS and Network Policy Server (NPS), including multifactor authentication integrations. This preserves an established enterprise authentication pattern, although policy decisions remain centered on the tunnel and the network path unless additional controls are layered on top.
Granular routing
Microsoft supports routing policies that can limit traffic to selected destinations and, in advanced scenarios, individual applications. Split-tunnel and route design should be treated as a security control, not merely a performance setting: every route determines which private resources the endpoint can attempt to reach.
Deployment options
Administrators can deploy an Always On profile with ProfileXML, PowerShell, Microsoft Intune, Configuration Manager, Windows Configuration Designer, or another mobile-device-management tool. The broad deployment choice is useful in mixed-management environments, but it also creates multiple places where profile versions, certificates, and routes can drift.
DirectAccess is a separate, older Microsoft technology. Microsoft says DirectAccess is deprecated for future Windows Server releases and identifies Always On VPN as its modern replacement. That statement does not require organizations to replace Always On VPN; the decision should be based on platform coverage, application scope, operational cost, and the desired security architecture.
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Microsoft Entra Private Access: best for identity-first application access
Microsoft Entra Private Access extends application-proxy capabilities to private resources regardless of TCP/IP port and protocol. Microsoft describes it as a cloud-based zero-trust network-access (ZTNA) service for private applications in hybrid, multicloud, private-network, and datacenter environments.
Why it is a strong Always On alternative
Entra Private Access changes the basic question from “May this endpoint join the corporate network?” to “May this authenticated user, on this device, access this private application right now?” Global Secure Access uses Microsoft Entra ID for single sign-on and can apply Conditional Access at the edge. Those policies can incorporate multifactor authentication, device compliance, named locations, and other identity or risk signals configured in the tenant.
For an organization already standardized on Microsoft 365 and Entra ID, the identity integration can reduce the number of separate authentication systems. Users can receive access to approved applications without receiving a broad route to every host in a private subnet.
Where it fits best
- Private web applications and business services distributed across datacenters, Azure, other clouds, and private networks.
- Workforces that include non-Windows endpoints or require consistent identity policy beyond domain-joined PCs.
- Security programs that want per-application Conditional Access and a smaller blast radius than a full network tunnel.
Questions to answer before migration
- Have you catalogued every application, hostname, port, protocol, dependency, and DNS name that users need?
- Does each candidate application work with the required access method, including any non-web or legacy protocol?
- Which users, groups, device-compliance states, and authentication strengths should be allowed?
- How will administrators publish, monitor, and troubleshoot connectors across each private environment?
Entra Private Access can replace a legacy VPN for applications that fit its access model, but it is not automatically a substitute for every use of a network tunnel. Keep a tunnel path for workloads whose dependencies cannot yet be represented as controlled application access.
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Zscaler positions Zscaler Private Access (ZPA) as a VPN alternative for hybrid workforces. Its product description promises direct, zero-trust access to private applications running on AWS or on-premises from any location or device. A 2026 Zscaler VPN-replacement brief presents ZPA as part of the company’s Zero Trust Exchange.
Why organizations shortlist ZPA
ZPA is designed around private-application access rather than extending a user onto a corporate LAN. That makes it a candidate for enterprises that want one policy plane for cloud and datacenter applications, especially when the workforce and endpoint estate extend beyond Windows.
The practical advantage is centralization: access rules can be expressed around users, groups, applications, and device context instead of separately maintaining broad network routes for every remote-user profile. The practical cost is a new platform, connector placement, endpoint deployment, policy model, and support process.
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Evaluation checklist
- Map your application inventory and verify that every required protocol is supported.
- Decide where connectors will run and how they will reach applications in each cloud, datacenter, or segmented network.
- Confirm integration with your identity provider, MFA method, directory groups, and device-management tooling.
- Test endpoint coverage for managed Windows, macOS, Linux, iOS, Android, and any approved BYOD scenario.
- Define ownership for policy administration, incident response, logging, and user support.
ZPA is most compelling when the objective is a broad zero-trust and SASE program, not merely a replacement for one Windows VPN profile. Compare the operational model and licensing terms with the effort required to keep Always On VPN correctly segmented.
Cloudflare One: best for a globally distributed access edge
Cloudflare One combines a globally distributed network with Zero Trust Network Access (ZTNA) to replace traditional VPN access to private networks. It is a natural candidate for organizations already using Cloudflare services or for distributed teams that want users to reach private resources through a broad access edge rather than a regional VPN concentrator.
What to validate
- Connector design: determine where private-network connectors run, how they reach internal segments, and how redundancy is provided.
- DNS behavior: test private names, split-DNS requirements, search domains, and what happens when a device changes networks.
- Device posture: define which device signals are required before an application policy permits access.
- Protocol support: verify the actual protocols used by each application, not just whether the application has a browser front end.
- Policy boundaries: ensure that a rule grants the intended application and does not unintentionally expose an entire private network.
Cloudflare One can reduce dependence on a conventional VPN client, but the migration still has engineering work. Private DNS, connectors, identity integration, endpoint posture, and application dependencies must be tested under real user conditions before the old tunnel is removed.
Azure VPN Gateway: the right answer when you still need a tunnel
Azure VPN Gateway remains a valid point-to-site modernization path in Microsoft’s zero-trust networking guidance. It is designed for organizations that still require network-level access to Azure virtual networks or connected networks but want stronger identity and policy controls than a basic shared-secret VPN.
Identity and Conditional Access
Azure point-to-site VPN can use Microsoft Entra ID authentication. Conditional Access policies can require multifactor authentication, a compliant device, or an approved named location before the tunnel is established. This preserves the familiar tunnel operating model while moving important decisions into identity policy.
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- Employees need SMB file shares whose access pattern depends on network paths.
- Administrators need RDP or management tooling across several private hosts.
- Legacy applications use protocols or dynamic connections that are difficult to publish individually.
- The organization is concentrated in Azure and wants a managed point-to-site entry path into connected networks.
Azure VPN Gateway does not provide the same application-level isolation as a ZTNA design. Use network security groups, route controls, least-privilege identity groups, and host-level authorization to reduce unnecessary reachability inside the tunnel.
Comparison of the leading alternatives
| Option | Access model | Identity and policy emphasis | Best fit | Key design question |
|---|---|---|---|---|
| Always On VPN | Auto-triggered user or device tunnel with granular routing | RADIUS/NPS MFA integrations, certificates, Windows policy, and route controls | Windows-centric estates needing seamless network access | Can routes and profiles be kept narrow enough for least privilege? |
| Microsoft Entra Private Access | Application-specific private-resource access without a traditional VPN | Entra ID single sign-on and Conditional Access at the edge | Microsoft 365 and Entra estates spanning hybrid, multicloud, and datacenter apps | Can each dependency be identified and published as an application? |
| Zscaler Private Access | Direct zero-trust access to private applications | Centralized policy in a dedicated ZTNA platform | Enterprises standardizing access across cloud and datacenter applications | Do connector, endpoint, identity, and licensing requirements fit the operating model? |
| Cloudflare One | ZTNA access to private networks through a distributed edge | Identity, device posture, and application policy | Distributed organizations seeking a globally distributed access edge | Will connector, DNS, posture, and protocol behavior meet application needs? |
| Azure VPN Gateway | Point-to-site network tunnel into Azure and connected networks | Entra ID authentication and Conditional Access, including MFA and device conditions | Legacy protocols, file shares, RDP, management tools, and broad private-network reach | Which network segments and hosts should the tunnel expose? |
Choose by workload and workforce
Remote access to on-premises file shares
File shares are a classic reason to retain network-level access. If users depend on SMB paths, mapped drives, namespace referrals, or file-server discovery, start by testing Azure VPN Gateway or a tightly scoped Always On VPN profile. A ZTNA product may work if its protocol and name-resolution behavior support the specific file-share design, but do not assume that a browser-based application policy covers SMB dependencies.
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RDP and administrative tooling
RDP, remote administration, and management agents often involve several hosts, ports, and supporting services. A tunnel can be simpler to operate for a controlled administrator group, provided network segmentation and host authorization remain strict. If the tooling can be represented as individual private applications, Entra Private Access or another ZTNA platform can reduce the amount of reachable network.
Private web applications
Private web applications are usually the easiest migration candidates. Inventory the application URL, dependencies, authentication flow, and administrator groups; then pilot app-level access with MFA and device conditions. Keep the existing tunnel available until users can complete their work and support staff can diagnose failures without guesswork.
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When users work from Windows, macOS, Linux, mobile devices, or approved BYOD, app-level services generally deserve priority in the evaluation. Always On VPN remains Windows-focused even though it supports several Windows join states. ZPA, Cloudflare One, and Entra Private Access should be assessed for endpoint coverage, posture signals, and the exact applications each platform can reach.
Organizations with mostly SaaS
If nearly every business workload is SaaS or a private application already protected by identity-aware access, a full VPN may no longer be necessary for most employees. Retain a narrowly scoped tunnel for the exceptions—such as a small administrator population or a legacy file service—rather than granting every user broad network reach.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.A migration plan that avoids a risky cutover
Microsoft’s guidance supports phased coexistence: onboard applications and users gradually while the legacy VPN remains available. The sequence below keeps the decision tied to measured business outcomes rather than a deadline.
- Inventory applications and protocols. Record owners, users, device types, hostnames, ports, transport protocols, DNS dependencies, authentication, and data sensitivity. Separate browser applications from file shares, RDP, management tools, and other network-dependent workloads.
- Classify users and devices. Identify Windows join state, management authority, operating systems, BYOD requirements, administrator privileges, and the device-compliance signals available to your identity provider.
- Define the target access model. Mark each workload as application-specific, subnet-level, or tunnel-required. Do not force a legacy protocol into an application model merely to meet a migration target.
- Select one low-risk pilot group. Choose a small application set with clear ownership and a manageable support audience. Keep Always On VPN or the existing tunnel available as a recovery path.
- Enforce identity conditions. Require MFA and apply device-compliance, risk, or named-location conditions appropriate to the application. Verify that denied access is logged and understandable to the help desk.
- Test real workflows. Measure sign-in success, DNS resolution, application response, reconnect behavior after sleep or network changes, and the support steps required for common failures. Do not rely only on a successful first login.
- Expand by application. Add the next workload only after the pilot owner accepts the security and operational results. Migrate groups in waves instead of exposing an entire subnet at once.
- Retire routes and profiles deliberately. Remove obsolete VPN routes, certificates, connector rules, and device profiles only after logs show that dependent traffic has moved and a rollback path is documented.
Operational pitfalls and recovery actions
Users can authenticate but cannot open the application
Check the application hostname, private DNS response, connector or gateway reachability, destination port, and authorization rule. Authentication proves identity; it does not prove that the private resource is reachable or that its dependencies are allowed.
A file share works on the tunnel but fails through ZTNA
Confirm the protocol and name-resolution requirements, including referrals and any supporting domain services. If the platform cannot represent the complete dependency chain reliably, keep that workload on a restricted network tunnel while moving simpler applications first.
Access is broader than intended
Review route advertisements, connector segments, wildcard host rules, group membership, and inherited policies. Replace broad subnet access with individual applications or narrower destinations where the workload permits it. For a tunnel that must remain broad, enforce host and network segmentation behind it.
Users lose access after sleep, roaming, or a network change
Test reconnect and reauthentication behavior on wired, Wi-Fi, and cellular networks. Check certificate validity, device posture freshness, DNS changes, and whether the endpoint client or tunnel service restarts correctly. Document the supported recovery action—reconnect, sign out, restart the service, or contact support—rather than asking users to repeatedly retry.
The help desk cannot tell which layer failed
Create a troubleshooting path that separates identity, device posture, endpoint client, DNS, connector or gateway, route, and application authorization. Capture correlation identifiers and timestamps in the access platform and gateway logs, and give support staff a least-privilege diagnostic view.
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No authoritative, comparable pricing or performance figure is established for these services in the available vendor material. Commercial terms can vary by user or device, minimum purchase, support tier, region, and negotiated agreement. Obtain current quotes directly from each vendor and include migration labor, connector infrastructure, endpoint-management changes, training, and parallel-run costs.
During evaluation, ask each provider to document regional availability, failover behavior, latency expectations, offline behavior, logging retention, service limits, and support escalation. Run these questions against your own application locations and user geography; a feature list alone cannot establish resilience for your environment.
Which option should you choose?
- Stay with Always On VPN when Windows is the dominant endpoint, automatic tunnels are working, and your users genuinely need network-level access. Improve route granularity, MFA, segmentation, and profile lifecycle before replacing a functioning control.
- Choose Microsoft Entra Private Access when Entra ID, Microsoft 365, Conditional Access, and hybrid private applications already define your identity architecture.
- Choose Zscaler Private Access when you want a dedicated ZTNA platform spanning private applications across cloud and datacenter environments and can support its connector and policy operations.
- Choose Cloudflare One when a globally distributed access edge and private-network ZTNA align with your connector, DNS, posture, and protocol requirements.
- Choose Azure VPN Gateway when broad private-network reach remains unavoidable for file shares, RDP, management tooling, or legacy protocols, but you want Entra authentication and Conditional Access around the tunnel.
The most defensible strategy for many remote workforces is not one universal replacement. Move suitable applications to identity-driven access, retain a narrow and well-governed tunnel for workloads that need it, and let application inventory and measured user outcomes determine each subsequent migration wave.
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