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Easy Setup Guide - One-Click iPod Sync

This guide shows you how to set up completely automatic syncing with minimal steps.

Goal: Make This Dead Simple

After setup, syncing should be as easy as:

  1. Plug in iPod
  2. Double-click an icon
  3. Done!

Quick Setup (5 Minutes)

Step 1: Run Initial Setup

cd /Users/jarren/Nextcloud/Documents/Resources/Scripts/plex-ipod-playlist-sync
./setup.sh

Step 2: Configure Auto-Mount for Your SMB Share

Edit config.yaml and fill in these sections:

plex:
  url: "http://YOUR_PLEX_SERVER_IP:32400"
  use_token: true
  token: "YOUR_PLEX_TOKEN"
  music_library: "Music"

  # Path mapping (what Plex reports vs. where files are on your Mac)
  path_mapping:
    server_path: "/Volumes/disk01/data/media/music"
    local_path: "/Users/jarren/Music/NesbittServer"

  # Auto-mount SMB share (the magic!)
  smb_mount:
    enabled: true
    smb_url: "Nesbitt Server._smb._tcp.local/disk01/data/media/music"
    mount_point: "/Users/jarren/Music/NesbittServer"
    username: "YOUR_SMB_USERNAME"
    # Password will be stored securely in macOS Keychain on first run

ipod:
  mount_point: "/Volumes/IPOD"
  music_dir: "/Volumes/IPOD/Music"
  playlist_dir: "/Volumes/IPOD/Playlists"

sync:
  mirror_mode: true

Important notes:

  • smb_url: Just the server and path part (NO smb:// prefix)
  • mount_point: Where you want it mounted on your Mac
  • username: Your SMB username
  • Password: You'll enter it once, then it's saved to Keychain

Step 3: First Run Test

./quick-sync.sh

What will happen:

  1. Script checks for iPod, mounts it if needed
  2. Asks for SMB password (first time only)
  3. Offers to save password to Keychain (say yes!)
  4. Shows you playlists
  5. Performs sync

From now on: Password is automatic, no typing needed!

Option 1: Terminal Launcher (Simplest)

Just run this whenever you want to sync:

./quick-sync.sh

What it does:

  • ✅ Auto-detects and mounts iPod
  • ✅ Auto-mounts SMB share (using saved password)
  • ✅ Shows menu: Dry run / Full sync / Quick sync
  • ✅ Offers to eject iPod when done

Option 2: Desktop Shortcut (One-Click)

Create a clickable desktop icon:

macOS - Using Automator App

  1. Open Automator
  2. Create new Application
  3. Add Run Shell Script action
  4. Paste this:
#!/bin/bash
cd /Users/jarren/Nextcloud/Documents/Resources/Scripts/plex-ipod-playlist-sync
./quick-sync.sh
  1. Save as iPod Sync on your Desktop
  2. (Optional) Right-click → Get Info → Change icon

Now: Just double-click the Desktop icon!

macOS - Using Shortcut (Even Better!)

  1. Open Shortcuts app
  2. Click + to create new shortcut
  3. Add Run Shell Script action: 
    cd /Users/jarren/Nextcloud/Documents/Resources/Scripts/plex-ipod-playlist-sync
./quick-sync.sh
  4. Save as "Sync iPod"
  5. Right-click shortcut → Add to Dock

Now: Click dock icon to sync!

Option 3: Auto-Run on iPod Connect (Fully Automatic)

Make it run automatically when you plug in your iPod:

Using Keyboard Maestro (Recommended)

  1. Download Keyboard Maestro (trial available)
  2. Create new macro:
    • Trigger: Volume Mounted (named "IPOD")
    • Action: Execute Shell Script
    cd /Users/jarren/Nextcloud/Documents/Resources/Scripts/plex-ipod-playlist-sync
./sync.sh --no-interaction

Now: Plug in iPod → Automatic sync!

Using Hazel (Alternative)

  1. Download Hazel
  2. Monitor /Volumes/
  3. When "IPOD" appears → Run script

For Non-Tech Users

Share this with family/friends who want to sync their iPod:

Ultra-Simple Instructions

Setup (One Time Only):

  1. Download the iPod Sync app from [shared location]
  2. Double-click it
  3. Enter your password when asked (only once)
  4. Click "Save to Keychain"

Every Time You Want to Sync:

  1. Plug in iPod
  2. Double-click iPod Sync app
  3. Press 2 for "Full sync"
  4. Wait for "SYNC COMPLETE"
  5. Press y to eject
  6. Done!

Even Simpler (If you set up auto-run):

  1. Plug in iPod
  2. Wait 30 seconds
  3. Unplug iPod
  4. Done!

Troubleshooting

"SMB share failed to mount"

Check:

  1. Can you access the server in Finder? (⌘K → smb://Nesbitt Server...)
  2. Is the server turned on?
  3. Is your Mac connected to the same network?

Fix:

  • Try mounting manually first to test credentials
  • Make sure smb_url doesn't have smb:// prefix
  • Check username/password are correct

"iPod not found"

Check:

  1. Is iPod plugged in?
  2. Does it appear in Finder?
  3. What's it called? (Should be "IPOD")

Fix:

  • If iPod is named differently, update mount_point in config.yaml
  • Try: diskutil list to see all drives
  • Manual mount: diskutil mount /dev/diskXsX

"Password prompt every time"

Keychain not saving:

  • Allow Keychain access when prompted
  • Check System Settings → Privacy → Full Disk Access
  • Try re-saving: Delete keychain entry and re-run

What Happens Automatically

When you run ./quick-sync.sh:

1. ✓ Check if iPod connected
   ↓ If not → Search and mount

2. ✓ Check if SMB share mounted
   ↓ If not → Mount using saved password

3. ✓ Connect to Plex

4. ✓ Show playlist status
   ↓ Ask if you want to change

5. ✓ Sync music
   ↓ Copy new, remove old

6. ✓ Ask if you want to eject

7. ✓ Done!

Total clicks needed: 3-4 (including password entry on first run) Time: 30 seconds - 5 minutes (depending on files to copy)

Summary: Setup Levels

Level Setup Time Usage Steps Best For
Terminal 2 min Run ./quick-sync.sh Tech users
Desktop Icon 5 min Double-click icon Most users
Auto-Sync 10 min Plug in iPod Everyone!

Questions? See main README.md for detailed documentation.

Created: 2025-10-29