Sunday morning project, set up Tailscale on most of my devices! Everything seems to be working and renamed devices to have appropriate names so I can access them from anywhere.
@payown I love Tailscale. It has so many other cool things too. I need to investigate those. Like Taildrop.
@stevenscott I honestly thought it was gonna take more time and be more of a headache to set up than it was. Now I’m just at the point where I’m like OK it’s done now what lol
@payown @stevenscott Tailscale is just fantastic. I have adblocking on all my devices via a Raspberry pi at home, regardless of whether I'm at home or on the road, because I set my tailscale DNs to always root through pi.
@FreakyFwoof @stevenscott So couple of questions for you! Are you using pie hole to block ads on all of your devices running through Tailscale? Is your pie an exit node or are you using a different device on your network as the exit note? And which pie are you using?
@payown @stevenscott PiHole, yes. Two pi 4's both with PiHole on, one as a fallback.
Don't even need to use exit nodes at all if you tell Tailscale that you're using custom DNS from the admin panel, and I put the Tailscale IP's of my pi's in, with even further fallback from quad9 dns so there are four name resolvers in there. First two are mine, last two are quad9's, if my home internet connection drops out for whatever reason.
@FreakyFwoof @stevenscott OK, I have a four that isn’t doing anything right now, so I think I have an afternoon project thank you, sir
@payown @stevenscott PiHole is just a must-have for anyone imo, especially these days.
@FreakyFwoof @payown @stevenscott agreed. I've been using it for over 10 years now, combined with Unbound for faster look ups via recursive caching.
@BorrisInABox @payown @stevenscott Did the same. Have a text file that should give you all the steps for unbound and pihole config if needed. worked for me twice, but I made the info for me so it's not best documented.
@FreakyFwoof @BorrisInABox @stevenscott Would love that text document if you don’t mind sharing
@payown @FreakyFwoof @BorrisInABox @stevenscott Has anyone else had trouble with Taildrop sending to iOS? It's never worked here. I choose send with Tailscale in context menu on a Windows machine, select the file in the list box, there's a line I can find with object nav saying one file to be sent, but the button showing my iPhone device name always stays dimmed. Both machines are connected in the admin pannel though. No idea what I'm missing, any advice appreciated.
@Scott @payown @BorrisInABox @stevenscott I've never tried it, as I only saw the option there last night, and I tried from one windows machine to another. Nothing came up though. Will try.
@Scott @payown @BorrisInABox @stevenscott Just tried it, phone threw up a notification the file had been received. Tapped it and it came up in the standard iOS files app. Not sure why your phone is dimmed unless it's offline or the version hasn't been updated maybe?
@FreakyFwoof @Scott @payown @stevenscott Yep, also works here. I sent a file from my NAS at home to my phone 500 miles away on mobile data. Worked fine.
@BorrisInABox @FreakyFwoof @payown @stevenscott Thanks for reporting back. It's up to date and showing as connected so I'm none the wiser, will fiddle more with it.

@Scott @BorrisInABox @payown @stevenscott To be doubly sure, open an admin command prompt/powershell and issue
tailscale update --yes

Or remove --yes if you want it to check with you before updating.

@FreakyFwoof @BorrisInABox @payown @stevenscott Yah tried that, it says "already running stable version 1.96.3; no update needed".
@Scott @BorrisInABox @payown @stevenscott OO, tailscale status.
Check your phone, does it show connected next to the IP, or say something like 'last seen...'
Maybe would explain why it's dimmed.
@BorrisInABox @FreakyFwoof @Scott @payown @stevenscott God I need to give Tailscale a go at some point lol.