Taildrop is the AirDrop Android users were missing

I use the Pixel 9 Pro as my daily driver and love it. But one notable feature I’ve always missed from the Apple ecosystem is AirDrop.

I typically have WhatsApp for Mac open and dump things there for quick access between devices. Clunky, but it worked.

Until I realized Tailscale —a VPN¹ that I love and use— has a feature called Taildrop. The name suggests it’s meant as an AirDrop competitor, and I’ve been super happy with it.

I can now send images uncompressed² to any of my devices. I’m not restricted by Bluetooth, proximity, or other limitations. Just need Tailscale running on the device.

Advantages

Not limited to the Apple ecosystem

Probably the highlight here is that Taildrop works on any device that supports Tailscale. So between a Pixel, iPhone, MacBook, Windows machine — no walls here.

Unlimited file size

There’s no filesize limit. In all fairness, AirDrop doesn’t have one either.

Taildrive

Another alpha feature they’re working on, similar to Taildrop, is Taildrive. It’s effectively a shared folder on the internet. If you’re on the same network (Tailnet), you can download files from this folder from anywhere.

This basically allows any folder on your device to become a mini NAS or file server. Bonkers!

Constraints

It’s not all sunshine and rainbows though. There are some constraints and issues with Taildrop.

Can only send to yourself

Even if you add another user to your Tailscale network, you can still only send files to yourself. I imagine this is still an early restriction, but the good news is that Tailscale is thinking about relaxing this over time (maybe).

This is clearly an area where AirDrop is superior since it can more conveniently allow you to send files to anyone nearby.

Note this doesn’t apply to Taildrive, just to Taildrop. With Taildrive, anyone on your Tailnet can access the shared files.

Can only send files

AirDrop handles sharing URLs or links elegantly. Share a URL from your phone to computer, and it automatically opens in your default browser. You can’t share links with Taildrop yet.

It’s a little buggy

When Taildropping from Android, I’ve noticed it occasionally caches the previous files that were sent. If you’re not carefully watching the preview, you can end up sending the wrong file.

In all fairness, Tailscale has labeled it as an alpha, so they get a pass on this. Their solutions are typically rock solid, so I fully trust when they graduate it from alpha, it’ll be production ready.

Despite these limitations, Taildrop has become an essential tool in my cross-device workflow. For Android users longing for AirDrop-like functionality, it’s worth setting up Tailscale for this feature alone. And if you’re already using Tailscale for other purposes, enabling Taildrop is a no-brainer.