OpenVPN vs Tailscale

Tailscale is a great alternative to OpenVPN (Access Server and CloudConnexa) in providing a comprehensive VPN solution that is performant and cost-saving, while being zero-config and can be set up in minutes. OpenVPN offers multiple products, including an open-source VPN solution that can be self-hosted called OpenVPN Access Server and a managed VPN service called CloudConnexa.

Tailscale vs OpenVPN comparison matrix

Here’s a quick visual comparison of where Tailscale and OpenVPN stand on a feature-by-feature basis. We’ll dive more into each feature ‌below.

Tailscale vs OpenVPN architecture overview and performance implications

OpenVPN’s core for both Access Server and CloudConnexa operates on a traditional hub-and-spoke VPN architecture. A central server exists that all clients connect to, with both the control plane and data plane flowing through it. For OpenVPN Access Server, there is a need to host the central server somewhere, with an option to fully self-host it. This comes with all the resource requirements of maintaining a server over time, including constant patching to prevent exploits and vulnerabilities.

CloudConnexa expands on Access Server with a network of points of presence, which they call Regions. These Regions are interconnected for more direct routes. CloudConnexa also uses Connectors, which are OpenVPN clients that establish persistent, always-on outbound tunnels to Regions. All control and configuration are handled through a centralized cloud portal. While CloudConnexa does remove the need for self-hosted server deployments for the user, these Connectors and Regions are still points of dependency.

Tailscale does not use a traditional model, instead employing an overlay mesh network with direct peer-to-peer connections. These direct connections are the data plane, which is facilitated by encrypted end-to-end WireGuard® tunnels. The control plane is separate from the data plane, where Tailscale uses a coordination server to help peers share public keys and addresses to establish direct connections.

Because WireGuard® is built into the kernel or runs in a high-efficiency module, it is capable of high throughput with low overhead. Furthermore, the distributed nature of this data plane means there is no single bottleneck like a gateway. Traffic takes the shortest path available through NAT traversal, improving reliability and latency.

Tailscale vs OpenVPN encryption and security

OpenVPN uses the OpenVPN protocol for all of its tunnels. This protocol is built on TLS/SSL and the OpenSSL cryptographic library. OpenVPN is not deny-by-default, and allows all connected endpoints to communicate. Admins need to manually switch to enforce a deny-by-default policy, leading to a risk of exposure. Additionally, an OpenVPN Access Server is typically reachable at a known IP and port, which presents a potential attack surface.

Tailscale’s basis on WireGuard® means a policy of deny-by-default. Tailscale’s data plane is also peer-to-peer and decentralized, meaning user data is kept private between the endpoints by design. When two devices communicate, they establish a direct WireGuard® tunnel with each other’s public keys. In effect, every pair of communicating nodes has its own private, secured channel. Effectively, Tailscale’s data plane is distributed without a singular device bottlenecking traffic.

As for encryption, Tailscale’s control plane employs a custom Noise IK-based protocol with X25519 as described in RFC7748. While it can operate directly over plain TCP in environments that allow it, it also supports being wrapped in TLS when necessary for compatibility or additional security requirements. Tailscale exclusively uses the WireGuard® protocol for its data plane, which has a fixed cryptographic suite including ChaCha20 for encryption and Poly1305 for authentication.

Both WireGuard® and OpenVPN have undergone security audits. WireGuard® is a significantly smaller codebase, making it easier to audit than OpenVPN.

Tailscale vs OpenVPN authentication

OpenVPN’s user authentication can be integrated with common existing identity systems like Okta or Azure. Administrators can manage user accounts in the OpenVPN Cloud portal or integrate with SSO/SAML, LDAP/Active Directory, etc. Multi-factor authentication (MFA) is supported via the OpenVPN Connect client or third-party identity provider integrations.

Device authentication is handled through digital certificates embedded in the connection profiles, ensuring that only devices with a valid certificate (tied to a user or connector) can establish tunnels​. CloudConnexa eases management by handling certificate issuance and verification behind the scenes​. However, for added security, it is necessary to use a third-party certificate management tool or PKI (Public Key Infrastructure).

Tailscale completely removes the need to manage certificates manually. Authentication happens natively with identity providers and SSO login. Users can authenticate with their provider of choice, such as Apple, Google, Microsoft, Okta, or other custom identity providers.

As for authorizing devices, Tailscale admins can approve new devices or configure auto-approval. This approval process adds an extra layer of security in case a user’s password is compromised. But even once on a tailnet, devices rely on cryptographic keys for trust, and an admin can centrally revoke a node’s key if a device is lost or stolen, instantly cutting off its access. This core principle works with Tailscale SSH, an SSH solution where you don’t need a password to directly SSH into devices.

Tailscale vs OpenVPN policy enforcement

Both OpenVPN and Tailscale have complex configurations allowing routing subnets, internet-bound traffic, and role-based access control.

OpenVPN allows administrators to define which network resources each user or group can access through the VPN via group-based access control. Under the hood, this is often achieved by managing iptables rules or routing rules per connected VPN client based on assigned privileges. Additionally, because Access Server can integrate with directory groups, you can map VPN access policies to user roles in your organization.

Tailscale uses identity-based access policies that include ACLs and Grants that allow for application-layer access control. ACL system. Administrators define an ACL policy (in JSON format) that specifies which users or groups can access which destinations (IP addresses or tags) and on which ports​. Administrators can specify policies per user and device name instead of IP addresses. Using groups and tags, administrators can implement Role-Based Access controls (RBACs) easily, with the ability to manage policy files via GitOps.

Tailscale vs OpenVPN initial setup and management

Setting up OpenVPN Access Server requires more initial planning and infrastructure. You need to deploy the Access Server software on a host. This could mean launching a VM from an AWS/Azure marketplace image, running a Docker container, or installing packages on a Linux VM. After installing the server, you’ll configure your networking with which subnets to allow, set up users, or connect it to your user directory, and have users install the OpenVPN Connect client.

CloudConnexa significantly reduces setup time compared to self-hosted OpenVPN, but involves more initial steps than Tailscale. It's a more involved process than Tailscale’s one-click login.

Once installed, OpenVPN users usually must actively click “Connect” in the VPN app whenever they need access, often leading to frequent re-authentication issues. Depending on client settings, they might also need to enter their credentials, such as username, password, and possibly MFA code each time. This creates a need for deliberate action from the user to connect to OpenVPN.

By contrast, Tailscale focuses on simplified installation and administration. From an end-user perspective, Tailscale often feels invisible. Configuration for Tailscale can be easily managed incrementally, so that users can connect to resources as soon as they join a network.

There is no hardware to deploy. Tailscale maintains the coordination server to exchange users’ public keys. All you need to get started is to create a Tailscale account (often by logging in with Google/Microsoft/Okta), install the client on two devices, and they instantly form a private network​. There’s no need to configure IP ranges, firewall rules, or NAT traversal because Tailscale handles all of that automatically.

Tailscale vs OpenVPN cost and pricing

OpenVPN Access Server is free if you fully self-host, though you still have to pay the associated costs of self-hosting. If not self-hosting, it is priced per connection. CloudConnexa, as the managed service offering, provides the conveniences missing from OpenVPN Access Server and is priced per seat.

Tailscale has flat pricing that is a straightforward charge per user. No hardware costs with networking appliances, and easy to set up without spending extra on resources. Reach out to our sales team today to get a demo.

The bottom line

OpenVPN is a traditional VPN in terms of requirements, architecture, initial setup, and long-term management. Tailscale provides a modern mesh network experience that yields better time-to-value, lends itself to cost savings, improves developer productivity, and is easy to set up and manage over time.

You can also check out how customers like Cribl, Awesome, Globalways, Bolt, Machinify, Corelight, and more have benefited from switching to Tailscale from OpenVPN.