Taildrop: Simple device-to-device file sharing via Tailscale

Last year, I shared a video about Tailscale, a personal VPN that has been transformative for how I manage my devices. Tailscale allows its users to connect all their devices seamlessly, no matter where they are in the world without opening ports on your router. It’s free to use, operates without requiring firewall adjustments, and adds a significant layer of security. Since that first video, I’ve discovered new ways to make the most of this tool, and one feature that stands out is Taildrop.

You can check out in this video review.

Taildrop makes transferring files across devices incredibly simple. Imagine an Android phone with a photo that needs to be sent to an iPhone. If you’re familiar with Apple’s AirDrop, you know how easy that process is but of course it doesn’t work on Android phones. Taildrop brings that same ease to any device in your network, regardless of the platform. Pull up the image, click the share button on your respective platform, select Tailscale and with a tap the image is transferred to the other device.

During a trip to Las Vegas for CES, I relied on Taildrop to send files from Nevada back to Connecticut with minimal effort. The process worked just as smoothly across continents as it does within the same room.

Getting started with Taildrop is straightforward. After enabling the feature in Tailscale’s admin panel, it syncs across all devices in the network. Once activated, files sent via Taildrop will typically land in the download folder on Android, Windows, and Mac. For iPhones, files appear in the Tailscale section of the Files app. The process is intuitive—just a few taps or clicks, and the file is delivered. Even large files are supported, though transfer speed depends on the available bandwidth.

One limitation I encountered is that the Mac and iOS versions don’t currently allow for file transfer resumption, so any interruption means starting over. Other platforms like Android and Windows are more forgiving, letting you pick up where you left off. This is an area where the feature will likely improve over time.

I’ve tested Taildrop in a variety of scenarios. For instance, on my Windows 11 ham radio computer, I transferred a capture of packet radio data to a MacBook Air in seconds. From the Mac, I sent a file to my Android phone, which appeared in its download folder as expected. With devices authenticated on the Tailscale network, there’s no need for additional approvals—files move securely and directly.

For users with NAS devices like Synology or QNAP, Taildrop requires some initial setup, but the process is well-documented on Tailscale’s support page. Once configured, it works just as seamlessly, depositing files into a specified folder for easy access.

This feature has become indispensable for me. Whether moving files between devices or remotely managing uploads, Taildrop handles it all effortlessly. Combined with the security and flexibility of Tailscale, it’s a tool I now rely on daily.

If you haven’t yet explored Tailscale, it’s worth a look. Beyond Taildrop, it has transformed how I manage my network, locking down outside access while maintaining full connectivity to all my devices and Docker containers. It’s a practical and powerful solution that continues to impress me.