Finish macOS setup with your normal administrator account. Keep the existing account if already configured. Connect power and the internet (Ethernet if convenient), and stay signed in while we set it up.

On Clipper, open Terminal and paste the block below. It names the Mac and adds Yacht’s existing public SSH key, preserving other authorized keys. Enter Clipper’s login password locally when sudo asks; it will not appear as you type.

Install the standalone macOS app from Tailscale. Sign into the same Tailscale network as Yacht and Starlight, allow its macOS prompts, and leave it connected. If Tailscale is already installed, use the existing installation. Note Clipper’s 100.x.x.x address in Tailscale. We will use macOS’s SSH server over this connection. Tailscale’s macOS variants.

In System Settings → General → Sharing → Remote Login, enable Remote Login and allow your account under Only these users. Full disk access for remote users can stay off for this bootstrap; we will enable appropriate backup access when needed. Apple’s Remote Login instructions.

Keep Clipper awake for this setup: open another Terminal tab, run caffeinate -i, and leave that tab open. Press Control-C when setup is finished. This is temporary; we will configure its normal server power behavior after connecting.

Send back the username printed above and Clipper’s Tailscale IP. For a verified first connection, also run ssh-keygen -lf /etc/ssh/ssh_host_ed25519_key.pub after Remote Login is enabled and send its SHA256 fingerprint. These are public connection details; keep your passwords and private keys on the Mac.

Optional head start: run xcode-select --install and accept the Command Line Tools installer if offered. If already installed, macOS says so. Screen Sharing can be added during the fleet desktop setup; it is not required for SSH.

Connect from Yacht using the supplied username/IP and verify the SSH host fingerprint. Record the actual hostname, CPU architecture, OS, RAM and attached disks. Create a clipper SSH alias, then verify noninteractive login. Add Starlight’s separately verified public key if needed; retain the laptops’ private keys on their original machines.

Install the development baseline using the machine’s architecture and each repository’s pinned tool versions: Command Line Tools, Homebrew, Git/GitHub CLI, Bun, Node/package managers, tmux, ripgrep, and project-specific compilers/runtimes. Reuse existing Codex, Claude Code and GitHub sign-ins from an authorized fleet host with Deck’s python3 bin/enroll-auth.py clipper (or --from-host starlight). Eric explicitly requested this workflow to avoid repeated logins. Secrets travel through encrypted SSH stdin into private credential storage, never repository files, logs or command arguments. Existing target logins are retained by default; private SSH keys remain per-host. Provider expiry and token refresh still apply. Eric enabled passwordless sudo for his Clipper account with /private/etc/sudoers.d/clipper-admin; removing that file revokes unattended administrator access.

Clone the private Deck repo into ~/Code/Deck, install its CLI, wire up ~/Code/AGENTS.md and handoffs, and verify deck context and deck sync. Install and pair Cyberdeck with the fleet, check its dashboard and session tools, and configure service startup and power behavior. Verify the actual available Cyberdeck release and preserve existing fleet services.

Restore or clone the selected project checkouts, then run their documented setup and representative builds/tests. Inventory unpushed branches, stashes, dirty files, untracked files, worktrees and remote-less projects on both laptops before transferring work. A fresh clone alone does not preserve that state. Verify Clipper is visible from both laptops and can run development/agent sessions before marking onboarding complete.

Homebrew and Apple Command Line Tools are installed, along with Git/Git LFS, GitHub CLI, Node 24, Bun, tmux, ripgrep, fd, jq, mise, direnv, rsync, ffmpeg and Seed CLI. Deck, Cyberdeck and a fresh Seed main checkout are at ~/Code. Seed’s ten pinned mise tools and dependencies installed successfully; the complete workspace typecheck passed. Laptop uncommitted work and private project archives remain on their source machines.

Codex and Claude Code both completed live requests returning CLIPPER_AUTH_OK. GitHub’s API authenticated Eric’s account. The reusable enrollment tool preserves existing logins on rerun and has five tests covering file permissions, preservation, private backups, symlink refusal and secret-free errors. Two stale Deck parser fixture expectations were corrected; all 45 Bun tests pass on Yacht, with Clipper verification recorded in Deck handoffs.

Cyberdeck serves http://clipper.tail0bb35a.ts.net:4777/; its API detects Codex, Claude and tmux. It is paired with Yacht, Starlight, Enuc, Sentinel and Iris. Iris pairing and authenticated proxy requests were verified in both directions on 2026-10-16. Iris previously stopped Cyberdeck after the final SSH logout because its systemd user manager had lingering disabled; sudo loginctl enable-linger eric fixes that lifecycle problem, and post-logout access was verified. Botical’s Tailscale client still reports NeedsLogin; its pairing remains a follow-up. Clipper can SSH to both laptops and the Enuc/Sentinel backup targets. Deck has synchronized successfully through GitHub.

Cyberdeck’s initial personal-folder inventory blocked the main thread in a filesystem open, preventing HTTP responses. Clipper now uses dataRoots: []; project scanning and the web API work. Set up bounded data inventory during the storage phase before re-enabling personal-folder scans. Evidence is in ~/.config/clipper-bootstrap/ on Clipper. The underlying scan behavior still needs investigation.

System sleep is disabled and power-loss restart is enabled. Deck/Cyberdeck LaunchAgents are registered in Eric’s GUI session; reboot/login recovery has not been tested. During development bootstrap, no drives were formatted and no laptop data was migrated or deleted. The later music phase copies data while retaining laptop originals.

Credential-transfer references: Codex auth-cache transfer, Claude credential storage, GitHub CLI token input.

Deck currently mirrors raw agent transcripts; that is not a full-machine backup. Extend storage coverage to applications and installation manifests; preferences, Application Support and containers; dotfiles and hidden configuration; project repositories and their complete local Git state; agent histories; documents, media and other data; and selected service databases with consistent backups.

First inventory Yacht, Starlight and Clipper’s attached storage, including formats, capacities, free space and existing contents. Keep each laptop’s archives in distinct host/date namespaces. Preserve macOS metadata, permissions, resource forks and extended attributes using a backup method tested for those requirements. Track cloud-only data and exclusions explicitly. Sensitive configurations and credential backups belong in encrypted storage, outside Deck and published documentation.

Design separate areas for versioned machine backups, long-term archives, and active shared data/projects. Do not merge the two home folders or overwrite Clipper’s live settings with either laptop’s entire Library. Retain application/version inventories alongside recoverable app data; restoration may require reinstalling software or signing in again. Determine actual compatibility and restore behavior during testing.

Before moving ownership of data to Clipper, verify checksums where applicable and perform representative restores of projects, app settings and files. Once Clipper holds the primary copy, maintain a separate verified backup on another device or location. Formatting, deleting laptop originals and service cutovers are separate actions requiring explicit intent. This bootstrap does not perform them.

Eric requested his music tools and data on Clipper, starting with Yacht’s Rekordbox instance, with actual remote app and playback verification. This is a copy; no source music or applications have been deleted.

Rekordbox 7.2.18.0311 is installed at /Applications/rekordbox 7/rekordbox.app, launches on Clipper, and has a Dock shortcut. Its application signature passes verification. The running app opens the copied Pioneer database. All 62 original track records are retained unchanged, with three playlists and six cues; startup adds 18 factory MERGE FX sampler records, bringing the live database to 80 entries. SQLite quick-check returns ok. A copied local track decodes with non-silent audio. These checks do not establish successful interactive playback in Rekordbox.

Of the 62 source entries, 39 reference local files and 23 reference Spotify. Thirteen source local files were readable and copied. The remaining 26 are under Yacht’s ~/Desktop/Abnormal Tracks, where macOS privacy blocks file reads. The source paths exist. Yacht’s ~/Music/Music, ~/Music/Logic, ~/Music/GarageBand, Documents and Desktop inventory are also blocked. Do not describe the library or whole music inventory as complete until those permissions are granted and the copy is resumed. The old PlotZone search preference is not a dependency of the current Rekordbox track records.

The accessible media inventory contains 49,332 files totaling 59,293,563,583 bytes, with SHA-256 hashes saved before migration verification. It covers Music/Production (including PML and SoundsMania), other readable Music contents, loose downloaded/home audio, ~/download, and selected PML/Hack Music Theory project and course folders. Bulk copying is still running at this checkpoint. An independent supervisor waits for the copy to finish, hashes the destination and writes the exact result; no successful final checksum claim has been made yet.

Ableton Live 12 Suite 12.4.3, Engine DJ, Lexicon and Mixxx, their available settings, and third-party music plugins/presets have also copied. Software/settings transfer size is 10,510,093,147 bytes; plugin/preset transfer size is 3,381,168,848 bytes. Both final software/settings and plugin/preset checksum comparisons completed with exit code 0 and zero differences. Signature checks passed for all five applications, including Rekordbox. Their licensing and interactive operation have not been tested. Native audio drivers/HAL components were not migrated.

Clipper currently denies both screen-capture and accessibility permission to the remote test process. Screenshot attempts fail; System Events automation times out or is refused. Eric was asked to enable Full Disk Access for Codex on Yacht and approve Automation/Accessibility/Screen Recording for the SSH helper on Clipper (typically sshd-keygen-wrapper). No permission database changes or bypasses were attempted. The requested remote screen and Rekordbox playback test remains pending.

Operational evidence and scripts are in ~/.config/clipper-music/ on Yacht and Clipper, outside Deck. On Yacht, transfer-lan.log tracks the remaining main copy; finish-verification.log tracks automatic destination verification; media-verify-result.json and software-verify-result.json are written when those checks finish. Source manifests, library comparisons and a pre-launch Pioneer snapshot are retained. Yacht’s finish-verification.py supervisor and its caffeinate process survive the shell session; sleep prevention ends when verification completes. Inspect live processes and logs before starting duplicate transfers.

After privacy approval, run Yacht’s resume-protected-files.py only after the main transfer finishes. It checks access, copies the four known blocked music roots and regenerates/verifies media hashes. Also inventory newly readable Documents/Desktop for additional music projects and plugin content before declaring all music migrated. Then remotely inspect Rekordbox’s actual window, resolve any sign-in/audio-output prompts, load and play an Abnormal Tracks file, and verify its waveform and advancing playhead. Spotify playback and other application activation remain separate live checks.

This checkpoint supersedes the source-permission and copy-in-progress status above. The agent runs as Codex CLI inside cmux on Yacht. Eric granted Full Disk Access to cmux; the earlier instruction to grant it to a Codex app was incorrect. Protected Music folders, Desktop and Documents are now readable. Their music was inventoried and copied, including all Abnormal Tracks, the Apple Music library, GarageBand material, additional loose tracks and music projects. Dictation and software-test recordings in Documents were excluded.

Final combined verification completed successfully: 55,361 files, 60,285,435,183 bytes, zero SHA-256 mismatches or missing files. All 39 local tracks referenced by Yacht’s original Rekordbox library were fully decoded on Clipper with ffmpeg, with zero failures. The 23 Spotify references remain streaming entries. All originals remain on Yacht; no cleanup was performed. No bulk copy remains running.

The live library retains all 62 original track records unchanged, three playlists and six cues; Rekordbox added 18 factory sampler entries during startup. It launches from its Dock shortcut. The five copied applications passed signature checks, support arm64 and are registered with LaunchServices. Clipper detects a DDJ-FLX4 and a USB audio interface; current Rekordbox settings select DDJ-FLX4 with master channels 1/2 and headphone channels 3/4. The agent did not alter that audio routing.

Still pending: Clipper reports screen-capture and Accessibility access as false for the remote test process. Eric was asked to add /usr/libexec/sshd-keygen-wrapper under System Settings → Privacy & Security → Accessibility and Screen & System Audio Recording, enable it, and approve Automation when prompted. Clipper’s Accessibility settings were opened. No permission bypass was attempted. Once granted, inspect the actual Rekordbox window, load an Abnormal Tracks file and verify waveform, advancing playback and audio output; test Spotify playback/sign-in as needed. File decoding and database integrity do not substitute for that requested interactive test. Other music application licensing and interactive behavior also remain untested.

Evidence is on Yacht and Clipper under ~/.config/clipper-music/: media-verify-result.json, library-audio-decode.json, software-verify-result.json, additional-music-verify.json, manifests and transfer logs. Yacht’s checkpoint.json now says files_verified_remote_gui_permission_needed; the hash inventory script includes the additional Desktop/Document music roots for later checks.