docs: add Tailscale integration design spec

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Joseph O'Brien
2026-04-16 23:55:43 -04:00
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# handoff-begin

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# Tailscale Integration Design
**Date:** 2026-04-16
**Status:** Approved
## Goal
Make notfiles environments ephemeral but reliable. A fresh machine runs `notstrap` and gets a
fully configured environment — no public GitHub exposure for dotfiles, no manual Tailscale setup,
no cloud dependency for secrets on bootstrap day.
## Overview
Add a `notnet` crate that owns Tailscale network presence, extend `notsecrets` with a
`YubikeySource`, and thread both into `notstrap`'s orchestration sequence. The dotfiles repo lives
on a private Gitea instance on minibox, reachable only over Tailscale.
## Crate Responsibilities
### `notnet` (new)
Owns all Tailscale concerns:
- Detect if Tailscale is already running (`tailscale status`)
- Install Tailscale if missing (package manager detection: `apt`/`brew`/`pacman`, fallback to
official install script)
- Resolve the auth key via priority chain (see below)
- Join the tailnet (`tailscale up --authkey=<key>`)
- Verify the target peer is reachable (ping by Tailscale hostname)
**Auth key resolution chain:**
1. `TS_AUTHKEY` env var
2. YubiKey PIV slot 9d (via `yubikey` crate)
3. Interactive prompt
**Public API:**
```rust
pub struct TailscaleOptions {
pub peer_hostname: String,
pub gitea_url: String,
pub install: bool,
}
/// Ensure this machine is connected to the tailnet and the target peer is reachable.
/// Returns immediately if Tailscale is already running.
pub fn ensure_connected(opts: &TailscaleOptions) -> Result<()>;
```
### `notsecrets` (extended)
New `YubikeySource` implementing `IdentitySource`:
- Uses the `yubikey` crate (pure Rust, no `ykman` dependency)
- Opens the first connected YubiKey
- Reads age private key material from PIV slot 9c
- Returns `Box<dyn Identity>`
Updated source resolution order in notstrap:
1. `--key-file` CLI arg
2. `YubikeySource` (PIV slot 9c)
3. `BitwardenSource`
4. `PromptSource`
### `notstrap` (updated)
`BootstrapOptions` gains:
```rust
pub tailscale: Option<TailscaleOptions>,
```
`None` = skip notnet entirely (existing machines, tests, CI).
`notstrap.toml` gains a `[tailscale]` section. When present, `gitea_url` is used as the clone
URL instead of `[bootstrap].dotfiles_repo`.
## YubiKey PIV Slot Layout
| Slot | Purpose | Managed by |
|------|----------------------------------|-------------|
| 9a | SSH authentication | 1Password |
| 9c | Age private key (dotfiles/SOPS) | notsecrets |
| 9d | Tailscale auth key | notnet |
Slot 9a is untouched — 1Password agent remains the primary SSH auth for day-to-day use.
## Configuration
`notstrap.toml` example with Tailscale enabled:
```toml
[bootstrap]
dotfiles_dir = "~/dotfiles"
bw_age_item = "age-key-dotfiles"
sops_file = "secrets/bootstrap.sops.env"
# dotfiles_repo is optional when [tailscale] is present
[tailscale]
peer_hostname = "minibox"
gitea_url = "http://minibox:3000/joe/dotfiles.git"
install = true
```
## Full Bootstrap Sequence
| Step | Crate | Skip condition |
|-------------------|---------------|---------------------------------------|
| 1. Prerequisites | notstrap | — |
| 2. Tailscale | notnet | Already on tailnet |
| 3. Clone dotfiles | notstrap/repo | Already cloned |
| 4. Age key | notsecrets | — |
| 5. Decrypt SOPS | notstrap | No injector configured |
| 6. Link dotfiles | notfiles | — |
| 7. Dot hooks | nothooks | — |
| 8. Setup hooks | nothooks | Already run (state file) |
## Error Handling
- If `TS_AUTHKEY` is unset and no YubiKey is connected and user declines prompt → clear error,
bootstrap aborts at step 2
- If Tailscale installs but peer is unreachable → error naming the peer hostname, bootstrap aborts
- If YubiKey slot 9c is empty → `YubikeySource` returns `Err`, resolver falls through to
`BitwardenSource`
- All steps follow the existing `StepStatus::Failed` / early-return pattern in notstrap
## Dependencies (new)
| Crate | Used by | Purpose |
|-------------|---------------------|-------------------------------|
| `yubikey` | notnet, notsecrets | PIV slot access (pure Rust) |
| `tailscale` | notnet | tailscale-rs SDK |
## Out of Scope
- Multi-YubiKey support (first connected device wins)
- Tailscale exit node or subnet router configuration
- Rotating auth keys automatically
- Windows support