A conversation started with:
“Is there an AirDrop for Windows?”
My answer was Tailscale, though that undersells it a bit.
What I like most is that it replaced several annoying parts of remote access for me:
• less messing with port forwarding
• less dealing with unreliable sync tools
• less thinking about network setup in general
Now I mostly just connect to the machine I need, by name, and keep moving.
I wrote up how I use it here:
https://taylorarndt.substack.com/p/you-should-be-using-tailscale
#Tailscale #Networking #SelfHosting
You Should Be Using Tailscale

You Should Be Using Tailscale

Taylor’s Substack
@tayarndt And I was just thinking about this while trying to force files to sync with Dropbox between an old Mac and this Windows computer...
@jane_jordan Tailscale amazing for that
@tayarndt Will it work between my very old Mac running Big Sur, my Windows 11 laptop, and my iPhone running iOS 26.something?
@tayarndt there is, it's called quick share
@J3317 @tayarndt I don't think that works between Windows and iPhone.
@alexchapman @J3317 Oh interesting. What about Windows to Mac?
@tayarndt @J3317 Hmm, not sure.
@alexchapman @J3317 Fascinating I’m gonna have to look it up. I know I’ve did it before but I just thought I would include it but yeah that’s fascinating.
@alexchapman @J3317 @tayarndt works between linux and windows but it's off topic 🙃
@J3317 I’ve never heard of this before
@tayarndt yeah, it's on windows and android, airdrop is being worked on for android last i herd it was coming to all phones at some point
@tayarndt I’ve heard of this for years, but I really need to start playing with it now that I will have more machines. Thank you. As always, your article was very well written and informative.
@technocounselor Yeah, I’ve got my MacBook Neo, my air, two surfaces and gaming computer that I have to keep things up and sync fun times and also the five or so linux servers
@technocounselor @tayarndt Yes this is awesome and unwound the complexities of Tailscale for me somewhat. There's still quite a bit that I wouldn't necessarily need but it sounds customizable enough that I can disable what I wouldn't need and some things sound like from your article that they're not even on by default.
@GamingWithEars @technocounselor @tayarndt I use it for accessing stuff when I'm not home, I haven't fully put everything on ts yet, I'm still working on the remote stuff, mapping out exit nodes, etc. but it's a fun thing. I might actually pay the $6 for it.
@tayarndt I really like this! Normally, I just use Remote Support via NVDA. But that doesn't allow me to send files between machines, nor can I listen to sounds on the controlled computer. I wish I knew about this much sooner. It sounds like a great way to transfer files if there is something I don't have on my thumb drive or even if I don't want to go to the other part of the house to copy from it to my external drive.
@tayarndt It might be a good idea to mention that this requires Windows 10 or later. If each machine must have a copy of the program running rather than simply logging in via a website, this means that older machines can't use this software.
@tayarndt how expensive it is?
@tayarndt Tailscale is one of those pieces of software that I genuinely don't know how I operated without before. Completely transformative. Another one of those is rclone. For Windows especially, that software is completely briliant.