Tailscale Breakthrough

Goal §

Access the server remotely from any network without relying on local IP or SSH tunnels.

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Setup §

Installed Tailscale:

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

Started:

sudo tailscale up

Logged in through browser.

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Common Commands §

Check status:

tailscale status

Get IP:

tailscale ip -4

Bring interface up:

sudo tailscale up

Bring interface down:

sudo tailscale down

Logout:

sudo tailscale logout

Ping another device:

tailscale ping <tailscale-ip>

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Initial Behavior §

• Worked correctly on mobile hotspot
• Could access server using:

100.x.x.x

• SSH and services worked

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Issue on Campus WiFi §

When connected to campus WiFi:

• Tailscale failed to connect
• Showed:
  • logged out
  • unable to reach control server
  • connection reset errors

Observed:

• Could not reach Tailscale servers
• Even tailscale up failed to authenticate

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Observation §

Campus network uses firewall (Sophos).

Behavior:

• Blocks Tailscale control traffic
• Prevents connection to coordination servers
• Breaks login and synchronization

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Workaround §

Connected server to mobile hotspot:

Hotspot → tailscale up → login works

Then switched back to campus WiFi.

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Interaction with VPN §

After enabling campus VPN:

• Tailscale started working again

Observation:

• VPN routes traffic differently
• Tailscale traffic goes through VPN tunnel
• Bypasses campus firewall restrictions

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Key Behavior §

Campus WiFi (no VPN) → Tailscale blocked
Campus WiFi + VPN → Tailscale works
Mobile hotspot → Tailscale works

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Notes §

• Tailscale depends on external coordination servers
• Campus firewall interferes with direct access
• VPN indirectly fixes this by tunneling traffic