🧵 “Why My Raspberry Pi Ghosted Me: Fixing Tailscale SSH When the 100.x IP Doesn’t Respond”

If you’ve ever installed Tailscale on a Raspberry Pi, got a shiny new 100.x.x.x IP, and confidently typed:

ssh [email protected]

…only for your terminal to stare back at you like:

ssh: connect to host 100.x.x.x port 22: Connection timed out

Congratulations — you’ve entered the same emotional support group I did.

This post is the guide I wish existed when I lost 40 minutes of my life yelling at an innocent Pi. If you’re going through the same thing right now, don’t worry — you’re among friends, and your Pi will stop ghosting you soon.

🥷 Quick Summary (for the impatient ninjas)

If Tailscale installed fine on your Pi but SSH doesn’t work, the problem is usually:

👉 You forgot to install Tailscale on the machine you’re SSHing from

Yes. It’s that simple. Don’t feel bad — I made the same mistake.

👉 The Pi is logged into Tailscale but not connected to the tailnet

tailscale status shows a lonely - in the connection column.

👉 Ping doesn’t work? That’s normal

Linux Tailscale blocks ICMP pings by default.

👉 Fix:

Install Tailscale on both devices, authenticate both, and SSH just works.

But let’s walk through it properly — with jokes, diagrams, and the exact commands.

🧩 The Setup: Raspberry Pi + Tailscale + My Sanity

I had a Raspberry Pi running Debian Trixie, and I wanted simple, secure, remote SSH access using Tailscale.

So I ran:

curl -fsSL https://tailscale.com/install.sh | sh
sudo tailscale up

Tailscale gave me:

100.125.xxx.xxx

Nice. Clean. Professional. I felt powerful.

But then…

ssh [email protected]

Boom:

Connection timed out.

I tried pinging it:

0 packets received.

My Pi was acting like I owed it money.

🔍 Diagnosis: What the Pi Was Actually Doing

Here’s what Tailscale showed on the Pi:

tailscale status

Output:

100.125.124.50  pi4  me@  linux  -

That last column is the problem.

It basically means:

“Yeah, I'm online... but I refuse to talk to anyone.”

The Tailscale tunnel was up, but the Pi wasn't connected to the tailnet because the other device (my laptop) wasn’t even on Tailscale.

So the Pi was sitting there, socially distancing.

🤦 The Missing Step (or: “Maybe I’m the problem?”)

I suddenly realized:

❗ I installed Tailscale on the Pi

❌ But not on my laptop

I know. I know. I’ll accept my L.

Tailscale is not like SSH or HTTP — the 100.x.x.x IPs only work inside the tailnet, and both devices must be on it.

🧯 The Fix (copy/paste these)

✔ 1. Install Tailscale on your laptop

Fedora:

sudo dnf install -y 'https://pkgs.tailscale.com/stable/fedora/tailscale.repo'
sudo dnf install -y tailscale

Or the universal installer:

curl -fsSL https://tailscale.com/install.sh | sh

✔ 2. Log in on your laptop

sudo tailscale up

Click the link. Approve the device.

✔ 3. Check that both devices see each other

On either machine:

tailscale status

Expected:

100.125.x.x   pi4       linux   active
100.88.x.x    fedora    linux   active

✔ 4. Now SSH works 🎉

ssh [email protected]

Or, with MagicDNS enabled:

ssh comon@pi4

Your Pi will finally stop ignoring your calls.

🖼 ASCII Diagram (for visual learners & 90s aesthetic lovers)

        BEFORE (Wrong)
        
      +------------+         (no Tailscale)
      |   Laptop   |-----------------------------------X
      +------------+           100.x.x.x unreachable

      +-------------+
      |   Pi 4      | 100.x.x.x (lonely)
      +-------------+

        AFTER (Correct)
        
      +-------------+      tailscale      +-------------+
      |   Laptop    | <-----------------> |    Pi 4     |
      | 100.88.x.x  |    (encrypted)      | 100.125.x.x |
      +-------------+                      +-------------+

                         SSH Works 🎉

🔧 Extra Debugging Commands (if you’re still stuck)

Check if the Pi is actually on the network:

tailscale ip -4

Check Tailscale tunnel health:

tailscale netcheck

Restart Tailscale cleanly:

sudo systemctl restart tailscaled

Enable Tailscale SSH (optional but awesome):

sudo tailscale up --ssh

Now you can SSH without needing your Pi’s local OS user account.

🧠 Final Thoughts

Tailscale is amazing — it gives you secure, NAT-punching, zero-config remote access without touching your router. But it's easy to make one small assumption:

“If my Pi has a 100.x.x.x address, I can SSH into it from anywhere.”

Nope. You must install Tailscale on both ends.

Once you do, everything “just works” — like magic, but nerdier.

Fixing Tailscale SSH When the 100.x IP Doesn’t Respond