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For most Windows-only organizations, Always On VPN is still the right answer when employees need an automatic, network-level tunnel. Replace it when your workforce is mixed-platform, when users should reach only specific applications rather than an entire subnet, or when you want identity and device-risk decisions at every application connection. In those cases, shortlist Microsoft Entra Private Access, Zscaler Private Access, and Cloudflare One. Keep Azure VPN Gateway for legacy protocols, file shares, management tools, or other workloads that genuinely require network-level connectivity.

The choice is not simply VPN versus no VPN. It is a decision about access scope, identity controls, endpoint coverage, private-network protocols, and the operational model your IT team can support.

What Always On VPN does—and why organizations replace it

Microsoft Always On VPN is a Windows 10, Windows 11, and Windows Server capability that creates automatically triggered user or device tunnels. It supports domain-joined, workgroup, and Microsoft Entra-joined devices; RADIUS and Network Policy Server (NPS) integrations for multifactor authentication; granular routing; and deployment through ProfileXML, PowerShell, Intune, Configuration Manager, Windows Configuration Designer, or another mobile-device-management system.

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Its strongest characteristic is continuity: a managed Windows device can establish a tunnel without asking an employee to launch a client each morning. Administrators can route only selected prefixes, or even traffic associated with individual applications, rather than sending every packet through the corporate network. Microsoft describes Always On VPN as a way to create advanced scenarios by integrating Windows operating systems and third-party solutions.

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The architecture becomes less attractive when requirements move beyond that model. A Windows-centric user-and-device tunnel does not automatically solve access for macOS, Linux, iOS, Android, contractors, or unmanaged bring-your-own devices. Network-level reach can also be broader than a zero-trust policy requires: once a user is on an approved subnet, several applications may be reachable unless routing and firewall rules are exceptionally precise. Certificate lifecycle, VPN profiles, DNS, NPS, gateways, and split-tunnel routes add operational dependencies.

Replacing Always On VPN therefore makes sense when one or more of these conditions apply:

  • Your workforce or application estate is materially multi-platform.
  • Users need one or two private applications, not broad subnet access.
  • Application owners want identity, device posture, multifactor authentication, and risk-based policy evaluated per connection.
  • You want to reduce lateral movement from a compromised endpoint.
  • You are standardizing on a cloud-delivered security edge and do not want to operate regional VPN gateways and profiles.

It does not make sense to replace it solely because a newer product uses zero-trust terminology. File services, RDP, administrative tools, and legacy TCP or UDP applications may still need a routable private-network path.

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Alternatives at a glance

Option Access model Best fit Important validation points Pricing information
Microsoft Entra Private Access Application-specific, identity-driven access to private resources Organizations already using Microsoft Entra ID, Microsoft 365, Conditional Access, and hybrid or multicloud applications Application inventory, connector placement, supported protocols, DNS behavior, device conditions, and licensing prerequisites Not stated; verify current Microsoft terms
Zscaler Private Access (ZPA) Zero-trust access to private applications through a dedicated security service Enterprises wanting a centralized ZTNA/SASE policy across cloud and datacenter applications Connector locations, identity integration, endpoint coverage, application discovery, support model, and license scope Not stated; obtain a current vendor quote
Cloudflare One Cloud-delivered Zero Trust Network Access to private networks and applications Distributed organizations that value a globally distributed access edge or already use Cloudflare services Connector design, DNS and routing behavior, device posture checks, protocol support, and policy granularity Not stated; verify the applicable plan and region
Azure VPN Gateway Point-to-site network-level VPN into Azure and connected networks Legacy protocols, file shares, RDP, administration, or broad private-network reachability that cannot yet be segmented by application Gateway topology, Entra authentication, Conditional Access, address space, routing, throughput requirements, and failover Not stated; calculate current Azure consumption and licensing costs

No authoritative comparative performance, adoption, or pricing figures are established here. Latency, capacity, service limits, and total cost depend on region, architecture, user count, connector placement, and contract terms.

1. Microsoft Entra Private Access

How it changes the access model

Microsoft Entra Private Access extends application-proxy capabilities to private resources without requiring a traditional VPN tunnel. Microsoft positions it as access to private corporate applications independent of TCP/IP port and protocol, across hybrid, multicloud, private-network, and datacenter environments. The user authenticates with Entra ID, and policy can evaluate identity, multifactor authentication, device compliance, and other Conditional Access signals before the connection is allowed.

Global Secure Access, the broader Microsoft zero-trust networking approach, replaces broad network tunnels with app-specific, identity-driven connections. That distinction is the central comparison with Always On VPN: the policy object is an application or private resource rather than a user being placed on a network.

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When it is the strongest replacement

  • Your identity directory is already Microsoft Entra ID and administrators use Conditional Access.
  • Applications are distributed between Azure, other clouds, private datacenters, and branch networks.
  • Security policy should differ by application, user group, device state, or sign-in risk.
  • Employees use more than Windows, or some access comes from devices that cannot carry a traditional corporate VPN profile.

Where it may not be a drop-in substitute

Map every required workload before removing a tunnel. A browser-based internal application and a file share are not equivalent migration units. Check how each application handles SMB, RDP, custom TCP or UDP ports, name resolution, service discovery, embedded links, and administrative tools. If an application expects unrestricted access to several subnets, an application-specific design may require multiple published resources, connector changes, or a temporary network-level path.

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Entra Private Access is also an architectural change, not merely a new client. Teams must design private-resource connectors, application definitions, DNS, Conditional Access policies, logging, and break-glass access. Pilot those controls with a low-risk application before moving business-critical systems.

2. Zscaler Private Access (ZPA)

What it provides

ZPA is positioned as a VPN alternative for hybrid workforces. Its model gives users direct, zero-trust access to private applications hosted on premises or in clouds such as AWS, without exposing the underlying network to the endpoint. A policy service, identity integration, and connectors mediate the application connection.

When to shortlist it

  • You want a dedicated ZTNA and SASE platform rather than a Microsoft-specific access stack.
  • Private applications span several cloud providers and datacenters.
  • Security operations needs centralized policy and visibility across a large application inventory.
  • You are prepared to operate connectors, endpoint software, identity integrations, and a vendor support relationship as a single platform.

Questions to answer in a proof of concept

  1. Can the connector placement reach every required application segment without opening unnecessary east-west paths?
  2. Does the endpoint client support all managed operating systems and the contractor or BYOD scenarios you actually have?
  3. How are private DNS names, split-horizon DNS, and service discovery handled?
  4. Do RDP, SMB, administrative consoles, custom TCP services, and any UDP-dependent applications work with the intended policy?
  5. Can identity, group membership, multifactor authentication, device posture, and session logging integrate with your existing systems?
  6. What happens when a connector, identity provider, endpoint client, or regional service path is unavailable?

Do not compare ZPA with Always On VPN by client-interface features alone. Compare the application inventory, connector topology, policy administration, endpoint support, incident workflow, and licensing model.

3. Cloudflare One

How the VPN-replacement approach works

Cloudflare One combines a globally distributed network with Zero Trust Network Access to provide remote access to private networks and applications. The intended outcome is similar to other ZTNA designs: authenticate the user and device, apply policy to the requested resource, and avoid placing the endpoint on a broad corporate subnet.

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Best-fit environments

  • Employees and contractors are geographically dispersed and benefit from a distributed access edge.
  • The organization already operates Cloudflare services and wants one policy and telemetry plane.
  • Private applications are being segmented by identity rather than published as an entire network.

Design checks before migration

Validate connector locations against the actual datacenter and cloud routes, not a simplified network diagram. Test private DNS resolution from each user population, including split-horizon zones and short names. Confirm whether device-posture checks cover the operating systems and management states in scope. Test every required protocol, especially file services, RDP, custom ports, and applications that rely on broadcast, multicast, or fixed source addresses. Document how policy behaves during an edge, connector, or identity-service outage.

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4. Azure VPN Gateway

Why it remains relevant

Azure VPN Gateway is the modernization path when the organization still needs a real network tunnel. Microsoft’s zero-trust networking guidance retains point-to-site VPN as a valid option and supports Entra ID authentication with Conditional Access policies such as multifactor authentication, device compliance, and named locations before the tunnel is established.

This approach preserves the operational concept of Always On VPN—an authenticated tunnel and routed private address space—while moving the gateway service into Azure and adding stronger identity checks. It is useful for legacy protocols, file shares, RDP, management tooling, and applications whose dependencies cannot yet be expressed as individual published resources.

Trade-offs

  • Security scope: A successful tunnel can provide access to multiple routes, so network segmentation and firewall rules remain essential.
  • Operations: You still own address planning, routing, DNS, client profiles, gateway design, monitoring, and failure recovery.
  • Reach: Azure-connected networks are straightforward; other clouds and datacenters require deliberate routing and connectivity design.
  • Policy: Entra authentication and Conditional Access improve admission control, but they do not automatically convert every application into a least-privilege resource.

Choose by access requirement, not product name

Use application-level access when

Users need a small, known set of internal web applications, APIs, or other supported private services. Application-level policy limits blast radius, makes access reviews easier, and lets security teams attach different requirements to different resources. It is usually the better direction for SaaS-heavy organizations and for teams adopting zero-trust controls.

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Use a network-level tunnel when

Users require several tightly coupled services, broad private-network reachability, legacy protocols, file shares, RDP, or management tools. Keep the tunnel as narrow as practical with route filters, firewall policy, device restrictions, and separate administrative access paths.

Use a hybrid model during transition

Most migrations do not need a single cutover date. Publish modern applications through an application-specific service while retaining Always On VPN or Azure VPN Gateway for workloads that still require network access. Remove routes and legacy profiles only after usage data and help-desk records show that the dependent applications have moved.

A decision framework for a remote workforce

Decision axis Questions to answer Why it matters
Access scope Does each role need an entire subnet, selected prefixes, or one application? Determines whether a VPN tunnel, segmented tunnel, or ZTNA policy is appropriate.
Identity and policy Which identity provider, MFA, Conditional Access, device posture, and risk signals are required? Defines how access is granted and re-evaluated.
Endpoint coverage Which Windows, macOS, Linux, iOS, Android, contractor, and BYOD cases must work? Exposes gaps in Windows-specific profile and client designs.
Private-resource fit Are SMB, RDP, TCP, UDP, legacy discovery, or fixed-address dependencies present? Prevents an application proxy from being selected for a workload that needs routing.
Operations Who owns clients, connectors, certificates, DNS, routing, policy, logging, and incident response? Reveals hidden staffing and migration costs.
Resilience and reach What regional presence, failover, latency, and offline behavior are acceptable? Connects architecture to the employee experience and recovery plan.
Commercial model Is licensing per user, device, connector, gateway consumption, or a combination? Prevents a technical shortlist from becoming an unaffordable deployment; current terms must be verified with each provider.

Migration plan: move by application and risk

  1. Inventory dependencies. Record every private application, protocol, port, DNS name, subnet, authentication method, user group, device type, and business owner. Include file shares, RDP, management systems, scheduled jobs, and applications that call another internal service.
  2. Classify access. Mark each workload as application-specific, segmented-network, or broad-network. Note which users need it and whether unmanaged devices are allowed.
  3. Choose a low-risk pilot. Select one application group with a clear owner, a small user population, and a rollback path. Avoid beginning with the identity provider, endpoint-management system, or an application with many undocumented dependencies.
  4. Define identity and device policy. Require multifactor authentication where appropriate, specify compliant-device or risk conditions, and create an emergency administrator path that does not depend on the same policy being tested.
  5. Deploy connectors and clients. Place connectors near the resources they serve, install endpoint components through your management system, and document DNS, routing, certificates, and outbound firewall requirements.
  6. Test real workflows. Test login, name resolution, file access, RDP, printing if required, application-to-application calls, sleep and resume, network changes, and recovery after a connector or identity-service interruption.
  7. Measure support impact. Track successful sign-ins, failed policy evaluations, latency complaints, reconnect behavior, and help-desk categories. Do not rely only on a technically successful login.
  8. Expand by application. Add the next group only after the pilot owner accepts the results. Keep the old tunnel available for workloads that have not been converted.
  9. Retire deliberately. Remove obsolete routes, certificates, profiles, firewall exceptions, and accounts. Update incident runbooks and verify that no scheduled task or administrative process still depends on the retired path.

Common failure modes and fixes

Users can sign in but cannot open the application

Check private DNS resolution first, then connector reachability, firewall rules, application bindings, and the exact hostname presented by the client. A policy that allows an application name does not help if the application redirects to a second internal hostname that was not published.

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File shares or RDP work inconsistently

Confirm that the selected architecture supports the required protocol and name-resolution method. Test direct IP, fully qualified names, authentication, and reconnect after sleep. If the workload needs several related services or broad subnet access, retain a segmented VPN path rather than forcing it through an application-only design.

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Only some devices receive access

Compare operating-system support, endpoint enrollment, certificate state, device-compliance signals, and Conditional Access results. Separate a policy denial from a missing client or connector by checking logs at each layer.

Performance is acceptable in one location but poor in another

Map the user’s path to the nearest service edge or connector, then compare the path to the private application. Connector placement, hairpin routing, DNS selection, and overloaded gateways can create regional differences even when the policy is identical. No universal latency or throughput figure should be assumed without testing your own regions and workloads.

The migration creates wider access than intended

Review routes, connector network reach, firewall rules, and group assignments. Start with deny-by-default application policies, publish only the required names and ports, and use separate administrative groups for elevated access.

What should you use for common scenarios?

Microsoft-centric, hybrid applications

Start with Microsoft Entra Private Access if Entra ID, Microsoft 365, and Conditional Access already govern your users and devices. Keep Azure VPN Gateway or the existing tunnel for workloads that cannot yet be expressed as application-specific access.

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Large heterogeneous enterprise

Evaluate Zscaler Private Access alongside Entra-based options when a dedicated, cross-cloud ZTNA platform and centralized policy are strategic requirements. Make the decision from connector, endpoint, identity, and application tests rather than brand familiarity.

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On-premises file shares, RDP, and legacy systems

Use a tightly controlled network-level design—Always On VPN or Azure VPN Gateway—until those dependencies are redesigned or replaced. Apply least-privilege routes, firewall segmentation, strong identity checks, and separate administrator policies.

Mostly private-cloud or SaaS applications

Ask whether employees need any private-network access at all. SaaS applications can use their own identity and access controls; private-cloud applications can often move to application-specific access. Retain a small, monitored network path only for the workloads that demonstrably need it.

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Always On VPN is not obsolete by definition

Microsoft identifies DirectAccess as deprecated for future Windows Server releases and names Always On VPN as the modern replacement for that older technology. That statement does not require an organization to replace Always On VPN. Decide based on platform coverage, application scope, security architecture, operational workload, and cost.

A well-managed Always On VPN deployment can remain appropriate for a Windows-only fleet with strong device management, carefully limited routes, reliable authentication infrastructure, and applications that genuinely need network connectivity. A zero-trust service is not automatically safer if its connectors, application inventory, identity policies, or recovery procedures are incomplete.

Bottom line

Choose Microsoft Entra Private Access for an Entra-centered, application-specific strategy; Zscaler Private Access for a dedicated enterprise ZTNA platform; Cloudflare One for a globally distributed access edge; and Azure VPN Gateway when network-level connectivity remains unavoidable. Run the migration in phases, preserve a controlled fallback for legacy workloads, and make the final decision from your application dependencies and endpoint population—not from the label attached to the product.

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