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Workforce Infrastructure P1

Install and configure Tailscale on karymsky

Assigneeprawnsue
Projectinfra
CreatedMar 10, 2026
UpdatedMar 10, 2026
networkinglinux

Description

Install Tailscale on karymsky and join the tailnet using a pre-placed auth key.

Acceptance Criteria

  • Tailscale is installed via the official install script
  • Tailscale is running and authenticated to the tailnet
  • tailscale status shows this machine as connected
  • Tailscale service is enabled on boot (systemd)
  • The auth key file is deleted after successful authentication
  • The machine’s Tailscale IP is noted in this task’s Notes section

Context

  • Auth key location: /tmp/tailscale-authkey (will be placed there before you start)
  • This is a Debian 13 machine (2012 MBA)
  • You are running as user prawnsue. You have passwordless sudo.
  • Tailscale is system-level — one install covers all users (prawnsue + lobsterdrew)
  • Do NOT reboot the machine. LobsterDrew is also running on this host.

Steps

  1. curl -fsSL https://tailscale.com/install.sh | sudo sh
  2. sudo systemctl enable --now tailscaled
  3. Read the auth key from /tmp/tailscale-authkey
  4. sudo tailscale up --authkey=<key>
  5. Verify: tailscale status
  6. Delete the auth key: rm /tmp/tailscale-authkey
  7. Note the Tailscale IP below

Dependencies

None

Notes

  • 2026-03-10 15:16 PDT — Started task and verified project context (board/projects/infra.md).

  • 2026-03-10 15:17 PDT — Confirmed /tmp/tailscale-authkey exists and is readable by prawnsue.

  • 2026-03-10 15:18 PDT — Blocked before install: sudo -n true fails with sudo: a password is required, so this host is not currently configured for passwordless sudo as stated in the task context.

  • 2026-03-10 15:18 PDT — Current state before any changes: tailscale binary not installed, tailscaled service inactive, auth key file still present at /tmp/tailscale-authkey.

  • 2026-03-10 15:18 PDT — Did not proceed further to avoid hanging on privileged commands or leaving a partial system-level install.

  • 2026-03-10 15:20 PDT — Re-checked task state during cron run: sudo -n true still fails with sudo: a password is required; tailscale remains uninstalled; tailscaled is still inactive; /tmp/tailscale-authkey is still present.

  • 2026-03-10 15:21 PDT — Attempted to use tool-level elevation as a fallback, but this session does not have elevated exec enabled, so I still cannot perform the required system-level install/auth steps from this environment.

  • 2026-03-10 15:26 PDT — Re-verified during scheduled board check: sudo -n true still fails with sudo: a password is required; tailscale is still not installed; tailscaled remains inactive; /tmp/tailscale-authkey is still present and unread changes have not been made.

  • 2026-03-10 15:27 PDT — Moving task to board/blocked/ per board workflow. Unblock requires either restoring passwordless sudo for prawnsue as described in task context, or reassigning to an execution environment that can perform privileged system changes on karymsky.

  • 2026-03-10 15:36 PDT — Re-checked during scheduled board run: sudo is still not passwordless for user ‘prawnsue’ (‘sudo -n true’ fails), Tailscale is still not installed, tailscaled is inactive, and the task remains blocked pending restored privileged access.

  • 2026-03-10 — Completed manually from avacha (Claude Code) via SSH. Passwordless sudo was fixed via lobsterdrew. Tailscale installed via apt, authenticated with auth key, key deleted. Agent cron timed out on the install (too slow for 2012 MBA within cron timeout).

  • Tailscale IPv4: 100.85.169.21

Decisions

board/in-review/infra-002-tailscale-karymsky.md In Review
Workforce Infrastructure P1

Install and configure Tailscale on tolbachik

Assigneecrankycrab
Projectinfra
CreatedMar 10, 2026
UpdatedMar 10, 2026
networkingmacos

Description

Install Tailscale on tolbachik and join the tailnet using a pre-placed auth key.

Acceptance Criteria

  • Tailscale is installed via Homebrew
  • Tailscale is running and authenticated to the tailnet
  • tailscale status shows this machine as connected
  • Tailscale is configured to start on boot (launchd)
  • The auth key file is deleted after successful authentication
  • The machine’s Tailscale IP is noted in this task’s Notes section

Context

  • Auth key location: /tmp/tailscale-authkey (will be placed there before you start)
  • This is a macOS 15.7 machine (2018 MBP)
  • You are running as user r2d22

Steps

  1. brew install tailscale
  2. sudo tailscaled install-system-daemon (sets up launchd auto-start)
  3. Read the auth key from /tmp/tailscale-authkey
  4. sudo tailscale up --authkey=<key>
  5. Verify: tailscale status
  6. Delete the auth key: rm /tmp/tailscale-authkey
  7. Note the Tailscale IP below

Dependencies

None

Notes

  • 2026-03-10 15:16 PDT — Installed Tailscale via Homebrew (tailscale 1.94.2).
  • 2026-03-10 15:16 PDT — Installed the system launchd daemon with sudo tailscaled install-system-daemon; verified com.tailscale.tailscaled is present in system launchd.
  • 2026-03-10 15:16 PDT — Authenticated this Mac to the tailnet using the pre-placed auth key.
  • 2026-03-10 15:16 PDT — Verified connectivity with tailscale status.
  • 2026-03-10 15:16 PDT — Deleted /tmp/tailscale-authkey after successful authentication.
  • Tailscale IPv4: 100.107.199.18

Decisions

board/in-review/infra-001-tailscale-tolbachik.md In Review

Done

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Blocked

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