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docs(readme): tailscale setup tutorial - #5

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WiktorStarczewski merged 1 commit into
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docs/tailscale-tutorial
Apr 24, 2026
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WiktorStarczewski merged 1 commit into
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Summary

New ## Tailscale setup section in the README, walking through the real-world sequence:

  1. Install (brew cask on macOS, link for other platforms).
  2. Approve the macOS Network Extension — the step most people miss. Without it the app spins forever and the Tailscale admin panel shows "waiting for your first device."
  3. Sign in and confirm the MagicDNS hostname.
  4. (Peer side) run hearsay normally — hearsay invite auto-picks up your tailscale hostname.
  5. (Consumer side) accept a Tailscale node share from the sender. Each side stays on their own tailnet — Tailscale's sharing feature is what bridges them.
  6. Verify with curl .../health before calling hearsay pair.

Also tightens the existing Prerequisites bullet — the previous wording "both machines join a shared tailnet" was misleading in practice, since users typically run separate personal tailnets and rely on node sharing.

Why

I hit every one of these steps live today onboarding to a peer's invite, including the Network Extension pitfall. Documenting the actual path so the next person doesn't have to re-discover it.

Test plan

  • Section renders correctly in GitHub's Markdown preview
  • Links inside the section resolve
  • CI green

Walks through the real-world flow after actually doing it end-to-end
today:

  1. Install via brew cask on macOS (other platforms linked).
  2. Approve the macOS Network Extension — without this the app hangs
     forever and the admin panel sits on 'waiting for your first
     device'. This is the step most people miss.
  3. Sign in; confirm the MagicDNS hostname.
  4. Peer side: run hearsay normally.
  5. Consumer side: accept a node share from the sender. Each side's
     own tailnet, bridged by Tailscale's sharing feature — no
     shared-tailnet membership required.
  6. curl /health to sanity-check reachability before 'hearsay pair'.

Also tightens the Prerequisites bullet so the 'both machines join a
shared tailnet' framing isn't misleading — in practice each person
keeps their own tailnet and sharing is what connects them.
@WiktorStarczewski
WiktorStarczewski merged commit 237a518 into main Apr 24, 2026
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@WiktorStarczewski
WiktorStarczewski deleted the docs/tailscale-tutorial branch April 24, 2026 15:13
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