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Tailscale Inc. is a software company based in Toronto, Ontario. Tailscale develops an open-source software-defined mesh virtual private network (VPN) and a web-based management service.[a][3][4] The company provides a zero config VPN as a service under the same name.[5]

The company’s name was inspired by a 2013 Google research paper, The Tail at Scale.[6][7]

History

In 2019, Google engineers Avery Pennarun, David Crawshaw, David Carney, and Brad Fitzpatrick founded Tailscale.[8]

In November 2020, Tailscale secured funding of US$12 million in a Series A round, led by Accel, with seed investors Heavybit and Uncork Capital participating.[9]

In May 2022, the company secured a US$100 million Series B round, led by CRV and Insight Partners, with participation from existing investors.[8][10]

In April 2025, the company secured a US$160 million Series C round, led by Accel, with participation from CRV, Insight Partners, Heavybit, and Uncork Capital.[11]

Software

The open-source software acts in combination with the management service to establish peer-to-peer or relayed VPN communication with other clients using the WireGuard protocol.[12][13]

Tailscale can open direct connection to the peer using NAT traversal techniques such as STUN or request port forwarding via UPnP IGD, NAT-PMP or PCP.[14] If the software fails to establish direct communication, it falls back to using DERP (Designated Encrypted Relay for Packets) protocol relays provided by the company.[15]

The IPv4 addresses given to clients are in the carrier-grade NAT reserved space. This was chosen to avoid interference with existing networks.[16]

The Linux client can also send traffic to networks behind itself by disabling SNAT and routing directly to the source IPs. [17]

Supported platforms

The Tailscale client software supports a number of operating systems and embedded software systems:[18]

The software also provides support for a Kubernetes operator[21] and Docker images.[22]

Features

Taildrop

Taildrop is an encrypted Peer-to-peer file sharing service that has entered a public alpha.[23] It is available to all users on all plans, once enabled from the admin console.[24][unreliable source?] Its user facing functionality is similar to AirDrop on iOS or Quick Share on Android (operating system).[25][26][27]

Exit Nodes

Exit Nodes, in a setup similar to Tor (network), is a node where Tailscale connects to the rest of the internet. These can be configured on most devices with Tailscale installed, and when this is done they act as the decryption point for your traffic.[28] Tailscale also started a public beta (a paid add-on),[29] partnering with Mullvad to allow users exit via Mullvad servers.[30][31][32]

See also

Notes

  1. ^ Although Tailscale provides VPN software and services, it should not be misconstrued to be what is commonly referred to as a VPN service, but note that Tailscale’s software can be integrated with the Mullvad VPN service.[2]

References

  1. ^ “Changelog”. Tailscale. Retrieved April 15, 2026.
  2. ^ Castro, Chiara (September 8, 2023). “Mullvad and Tailscale join forces in the name of online security”. TechRadar. Retrieved April 15, 2026.
  3. ^ Rogers, Sarah (September 9, 2021). “Tailscale VPN review”. TechRadar. Archived from the original on September 9, 2021. Retrieved April 13, 2022.
  4. ^ Vaughan-Nichols, Steven. “Tailscale launches Wireguard-secured mesh network”. ZDNet. Archived from the original on April 13, 2022. Retrieved April 13, 2022.
  5. ^ Hanselman, Scott (January 22, 2021). “Using Tailscale on Windows to network more easily with WSL2 and Visual Studio Code”. www.hanselman.com. Archived from the original on January 22, 2021. Retrieved February 1, 2021.
  6. ^ Dean, Jeffrey; Barroso, Luiz André. “The Tail at Scale”. Google. Archived from the original on February 21, 2020. Retrieved March 9, 2021.
  7. ^ Pennarun, Avery; Fitzpatrick, Brad (January 15, 2022). Tailscale with Avery Pennarun and Brad Fitzpatrick. Security Cryptography Whatever. Event occurs at 45m53s. Archived from the original on February 23, 2023. Retrieved February 23, 2023 – via archive.org.
  8. ^ a b Wiggers, Kyle (May 5, 2022). “Tailscale lands $100 million to ‘transform’ enterprise VPNs with mesh technology”. TechCrunch. Archived from the original on May 5, 2022.
  9. ^ Dillet, Romain (November 10, 2020). “Tailscale raises $12 million for its WireGuard-based corporate VPN”. TechCrunch. Archived from the original on February 20, 2026. Retrieved February 1, 2021.
  10. ^ Tailscale (May 4, 2022). “Tailscale raises $100M… to fix the Internet”. Tailscale. Archived from the original on May 4, 2022. Retrieved May 5, 2022.
  11. ^ Tailscale (April 8, 2025). “Building the New Internet, together — our Series C and what’s next”. Tailscale. Archived from the original on April 8, 2025. Retrieved November 28, 2025.
  12. ^ Morgan, Ethel. “Tailscale”. ethulhu.co.uk. Archived from the original on February 5, 2021. Retrieved February 2, 2021.
  13. ^ “What is Tailscale?”. Tailscale. Retrieved August 17, 2024.
  14. ^ “Troubleshooting device connectivity”. Tailscale. Retrieved August 17, 2024.
  15. ^ “Terminology and concepts”. Tailscale. Retrieved August 17, 2024.
  16. ^ “IP pool · Tailscale Docs”. Tailscale. Retrieved August 17, 2024.
  17. ^ “Disable SNAT”. Tailscale. Retrieved March 15, 2025.
  18. ^ “Download”. Tailscale. Retrieved March 7, 2024.
  19. ^ “Access Synology NAS from anywhere”. Tailscale. Retrieved March 7, 2024.
  20. ^ “QNAP”. Tailscale. Retrieved March 7, 2024.
  21. ^ “Kubernetes operator”. Tailscale. Retrieved March 7, 2024.
  22. ^ “Contain your excitement: A deep dive into using Tailscale with Docker”. Tailscale. Retrieved March 7, 2024.
  23. ^ “Taildrop · Tailscale Docs”. Tailscale. Retrieved January 9, 2026.
  24. ^ “Advanced Tailscale Applications: Taildrop, Exit Nodes, and Subnet Routing Configuration”. WellWells. February 18, 2025. Retrieved January 9, 2026.
  25. ^ Leroux, Faith (July 5, 2020). “How to use Quick Share, Android’s AirDrop alternative”. Android Police. Retrieved January 9, 2026.
  26. ^ “Use AirDrop on your iPhone or iPad – Apple Support (CA)”. Apple Support. Retrieved January 9, 2026.
  27. ^ Gopal, Kaushik. “Taildrop – transfer files between Android and MacOS – Kaushik Gopal’s Website”. kau.sh. Retrieved January 9, 2026.
  28. ^ Henderson, Marty. “Feb. 4th, 2022”. Tailscale Exit Nodes.
  29. ^ “Surf the Web Privately with Mullvad’s Global Network + Tailscale”. tailscale.com. Retrieved January 9, 2026.
  30. ^ “Tailscale has partnered with Mullvad”. Mullvad VPN. September 7, 2023. Retrieved January 9, 2026.
  31. ^ “Mullvad exit nodes”. Tailscale. Retrieved January 9, 2026.
  32. ^ “Tailscale, Mullvad, and More”. Server As Code Dot Com. November 23, 2024. Retrieved January 9, 2026.

Bibliography