Choose WireGuard if…
You can deploy Self-hosted on Linux (in-kernel since 5.6), BSD, macOS, Windows, iOS, Android; commonly deployed via Linux servers, OPNsense, pfSense, or as the foundation of managed services like Tailscale and Cloudflare WARP.
Free / OSS licensing fits your budget — Free (GPL-2.0); WireGuard is a protocol and reference implementation, not a managed service.
You prioritise Modern cryptography (ChaCha20-Poly1305, Curve25519, BLAKE2s, Noise handshake), small codebase (~4,000 lines vs OpenVPN's ~100,000+), high performance with low CPU overhead, merged into Linux kernel by Linus Torvalds in 2020, kernel-level performance, well-suited for mobile due to fast handshake and low battery drain, foundation for major commercial VPN and ZTNA platforms.
Choose Tailscale if…
You can deploy SaaS coordination plane + WireGuard peer-to-peer data plane; clients on Windows, macOS, Linux, iOS, Android; self-hostable coordination via open-source Headscale.
Freemium / Paid licensing fits your budget — Free Personal (up to 6 users, unlimited devices); Standard $8/user/mo; Premium $18/user/mo; Enterprise custom.
You prioritise Built on WireGuard for high performance and modern cryptography, near-zero configuration (install client, authenticate, you're on the network), peer-to-peer architecture means low latency and no central bottleneck, MagicDNS automatically assigns human-readable names, ACLs enable identity-based zero-trust access, NAT traversal handles tricky network topologies, genuinely useful free tier, open-source Headscale provides self-hostable coordination.