bootstrap.sh

#!/usr/bin/env bash
# Bootstrap script for fresh macOS setup with chezmoi dotfiles
# Usage: curl -fsSL https://gist.githubusercontent.com/.../bootstrap.sh | bash

set -euo pipefail

echo "🚀 Starting dotfiles bootstrap..."

# 1. Install Homebrew if not present
if ! command -v brew &>/dev/null; then
    echo "📦 Installing Homebrew..."
    /bin/bash -c "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/HEAD/install.sh)"

    # Add Homebrew to PATH (Apple Silicon)
    if [ -d /opt/homebrew/bin ]; then
        eval "$(/opt/homebrew/bin/brew shellenv)"
    fi
    echo "✅ Homebrew installed"
else
    echo "✅ Homebrew already installed"
fi

# 2. Install essential packages
echo "📦 Installing chezmoi and gnupg..."
brew install chezmoi gnupg
echo "✅ Essential packages installed"

# 3. Setup iCloud Secret directory (auto-create if missing)
ICLOUD_SECRET="$HOME/iCloud/Shared/Secret"
if [ ! -d "$ICLOUD_SECRET" ]; then
    echo "📁 Creating iCloud Secret directory structure..."
    mkdir -p "$ICLOUD_SECRET"/{gpg,ssh}

    cat > "$ICLOUD_SECRET/README.md" <<'EOREADME'
# iCloud Secret Directory

This directory stores sensitive files that should NOT be committed to Git.

## Structure
- gpg/ - GPG private keys
- ssh/ - SSH private keys

## Setup Instructions
See chezmoi repository: docs/icloud-secret-setup.md
EOREADME

    echo "⚠️  iCloud Secret directory created but empty."
    echo "    Please export GPG and SSH keys to:"
    echo "    - $ICLOUD_SECRET/gpg/"
    echo "    - $ICLOUD_SECRET/ssh/"
    echo ""
    echo "    See setup guide in chezmoi repo after initialization."
fi

# 4. Get machine type from user
read "?Enter machine type (work/personal): " MACHINE_TYPE
while [[ ! "$MACHINE_TYPE" =~ ^(work|personal)$ ]]; do
    echo "❌ Invalid input. Please enter 'work' or 'personal'"
    read "?Enter machine type (work/personal): " MACHINE_TYPE
done

# 5. Import GPG key from iCloud
echo "🔐 Importing GPG key..."
GPG_KEY_PATH="$ICLOUD_SECRET/gpg/private-key-$MACHINE_TYPE.asc"
if [ -f "$GPG_KEY_PATH" ]; then
    gpg --import "$GPG_KEY_PATH"
    echo "✅ GPG key imported"
else
    echo "⚠️  GPG key not found at: $GPG_KEY_PATH"
    echo "    You'll need to import it manually later."
    echo "    Command: gpg --import $GPG_KEY_PATH"
fi

# 6. Setup SSH key for GitHub access (required for private repo)
echo "🔑 Setting up SSH key..."
SSH_KEY_PATH="$ICLOUD_SECRET/ssh/id_ed25519_$MACHINE_TYPE"
if [ -f "$SSH_KEY_PATH" ]; then
    mkdir -p ~/.ssh
    chmod 700 ~/.ssh

    # Create symlink
    ln -sf "$SSH_KEY_PATH" ~/.ssh/id_ed25519
    ln -sf "${SSH_KEY_PATH}.pub" ~/.ssh/id_ed25519.pub
    chmod 600 ~/.ssh/id_ed25519

    # Add to ssh-agent
    eval "$(ssh-agent -s)"

    # Wait for agent to be ready
    sleep 1

    if ssh-add ~/.ssh/id_ed25519 2>/dev/null; then
        echo "✅ SSH key added to agent"
    else
        echo "⚠️  Failed to add SSH key to agent"
        echo "   You may need to run manually: ssh-add ~/.ssh/id_ed25519"
        echo "   Continuing anyway..."
    fi

    echo "✅ SSH key configured"
else
    echo "❌ SSH key not found at: $SSH_KEY_PATH"
    echo "    Cannot proceed without SSH key for private repository."
    echo ""
    echo "📝 Manual setup required:"
    echo "    1. Copy SSH keys to $ICLOUD_SECRET/ssh/"
    echo "    2. Re-run this bootstrap script"
    exit 1
fi

# 7. Check network connectivity
echo "🌐 Checking network connectivity..."
if ! ping -c 1 github.com &>/dev/null; then
    echo "❌ Cannot reach github.com - check your network connection"
    exit 1
fi

# 8. Initialize chezmoi repository (using SSH URL for private repo)
echo "📥 Initializing chezmoi repository..."
chezmoi init [email protected]:private-junseokh/chezmoi-dotfiles.git

# 9. Configure machine type in chezmoi config
echo "⚙️  Configuring chezmoi..."
mkdir -p ~/.config/chezmoi

# Detect GPG key ID
GPG_KEY_ID=$(gpg --list-secret-keys --keyid-format LONG 2>/dev/null | grep sec | awk '{print $2}' | cut -d'/' -f2 | head -n1)

cat > ~/.config/chezmoi/chezmoi.toml <<EOF
encryption = "gpg"

[gpg]
    recipient = "$GPG_KEY_ID"

[data]
    machine_type = "$MACHINE_TYPE"

    # Personal info
    name_personal = "Junseok Hyun"
    email_personal = "[email protected]"
    gpg_key_personal = "CB5A764C7AC650D7"

    # Work info
    name_work = "Junseok Hyun"
    email_work = "[email protected]"
    gpg_key_work = "C4F9C757F830678D"
EOF

echo "✅ Configuration created"

# 10. Apply dotfiles (this will trigger all run_once and run_before scripts)
echo "🔄 Applying dotfiles..."
chezmoi apply --refresh-externals

echo ""
echo "✅ Bootstrap complete!"
echo ""
echo "📝 Next steps:"
echo "   1. Restart your terminal to load new shell configuration"
echo "   2. Run 'devcheck' to verify setup"
echo "   3. Install missing Homebrew packages: brew bundle install"

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