start/wait for time machine backup, then update mac

backup-and-update.sh

#!/usr/bin/env bash
#
# backup-and-update.sh
#   1) Prevent system sleep (via caffeinate)
#   2) Run (or detect) a Time Machine backup
#   3) Wait for the backup to finish
#   4) If the target macOS installer is present:
#        • launch startosinstall (major upgrade → reboot)
#      Else if the target macOS update is downloaded (from Software Update):
#        • install it using softwareupdate command
#      Else:
#        • list & install all minor/security updates
#   5) Reboot (shutdown -r now)
#
# Options:
#   --test  Test mode - only log information without performing actions
#
# Environment Variables:
#   TARGET_MACOS_NAME    Name of the macOS version to update to (default: "Sequoia")
#   TARGET_MACOS_VERSION Version number to update to (default: "15")
#
# Setup:
#   • In ~/.env:
#       DISCORD_WEBHOOK_URL="https://discord.com/api/webhooks/…"
#   • chmod 600 ~/.env
#   • chmod +x ~/bin/backup-and-update.sh
#
# Examples:
#   ./backup-and-update.sh                      # Update to macOS Sequoia
#   TARGET_MACOS_NAME=Sonoma ./backup-and-update.sh  # Update to macOS Sonoma
#   TARGET_MACOS_NAME="Ventura" TARGET_MACOS_VERSION="13" ./backup-and-update.sh  # Update to macOS Ventura

set -euo pipefail

echo -ne "WARNING: make sure you've given the terminal you're executing this script with the \"Full Disk Access\" permission in the \"Security & Privacy\" Settings on your Mac. Otherwise, this will not work. Cheers.\n\n\n"

# Default target macOS version if not specified
TARGET_MACOS_NAME="${TARGET_MACOS_NAME:-Sequoia}"
TARGET_MACOS_VERSION="${TARGET_MACOS_VERSION:-15}"

# Parse arguments
TEST_MODE=false
for arg in "$@"; do
  case $arg in
    --test)
      TEST_MODE=true
      echo "🧪 TEST MODE ACTIVE - No installations or reboots will be performed"
      echo "📋 Target macOS: $TARGET_MACOS_NAME (version $TARGET_MACOS_VERSION)"
      ;;
  esac
done

#–– load discord webhook
if [ -f "${HOME}/.env" ]; then
  # shellcheck source=/dev/null
  source "${HOME}/.env"
fi
: "${DISCORD_WEBHOOK_URL:?Set DISCORD_WEBHOOK_URL in ~/.env}"
WEBHOOK_URL="$DISCORD_WEBHOOK_URL"
DISCORD_SCRIPT="/Users/jason/scripts/discord.sh/discord.sh"

#–– helper to send an embed
send_embed() {
  local title="$1" desc="$2" color="${3:-3447003}"

  # In test mode, only log the embed info
  if [[ "$TEST_MODE" == true ]]; then
    echo "📤 DISCORD EMBED (TEST MODE)"
    echo "   Title: $title"
    echo "   Description: $desc"
    echo "   Color: $color"
    return 0
  fi

  # Escape special characters in the description
  local escaped_desc
  escaped_desc=$(echo -n "$desc" | perl -pe 's/\n/\\n/g; s/\r/\\r/g; s/\t/\\t/g')

  # Use discord.sh correctly with its expected parameters
  "$DISCORD_SCRIPT" \
    --webhook-url="$WEBHOOK_URL" \
    --title "$title" \
    --description "$escaped_desc" \
    --color "$color"
}

#–– prevent sleep (skipped in test mode)
if [[ "$TEST_MODE" == false ]]; then
  caffeinate -dimsu &
  CAFFE_PID=$!
  trap 'kill "$CAFFE_PID"' EXIT
else
  echo "🔋 TEST MODE: Skipping caffeinate process"
fi

#–– announce start
host_info="Host: $(hostname)
Time: $(date +'%Y-%m-%d %H:%M:%S')
macOS: $(sw_vers -productName) $(sw_vers -productVersion) ($(sw_vers -buildVersion))
Architecture: $(uname -m)
Target: macOS $TARGET_MACOS_NAME ($TARGET_MACOS_VERSION)"

send_embed "Backup & Update Started" "$host_info" 3447003

#–– 1) Time Machine
if [[ "$TEST_MODE" == true ]]; then
  echo "💾 TEST MODE: Skipping actual Time Machine backup"
  echo "Current Time Machine status:"
  tmutil status
  echo "Recent Time Machine backups:"
  tmutil listbackups | tail -5
else
  phase=$(tmutil currentphase 2>/dev/null || echo "NotRunning")
  t0=$(date +%s)
  if [[ "$phase" == "NotRunning" ]]; then
    send_embed "Time Machine Backup" "Starting backup…" 15844367
    tmutil startbackup --auto
  else
    send_embed "Time Machine Backup" "Already in progress (phase: $phase). Monitoring…" 15844367
  fi

  echo -n "Waiting for backup"
  while true; do
    phase=$(tmutil currentphase 2>/dev/null || echo "NotRunning")
    if [[ "$phase" == "NotRunning" ]]; then
      echo " ✔"
      break
    fi
    echo -n "."
    sleep 60
  done
  t1=$(date +%s)
  send_embed "Backup Complete" \
    "Duration: $((t1-t0))s
Finished at: $(date +'%Y-%m-%d %H:%M:%S')" \
    3066993
fi

#–– 2) Check for macOS major upgrade methods

# First, check if we have the full installer app
installer_app=$(find /Applications -maxdepth 1 -type d -iname "Install macOS $TARGET_MACOS_NAME*.app" | head -n1)

# Print debug info in test mode
if [[ "$TEST_MODE" == true ]]; then
  echo "🔍 CHECKING FOR $TARGET_MACOS_NAME INSTALLER APP"
  if [[ -n "$installer_app" ]]; then
    echo "✅ Found installer app: $installer_app"
    echo "   Last modified: $(stat -f '%Sm' "$installer_app")"
    echo "   Size: $(du -sh "$installer_app" | cut -f1)"
    echo "   Version info:"
    plutil -p "$installer_app/Contents/Info.plist" | grep -E "CFBundleShortVersionString|CFBundleVersion"
    echo "   startosinstall path exists: $([[ -x "$installer_app/Contents/Resources/startosinstall" ]] && echo "Yes" || echo "No")"
  else
    echo "❌ No macOS $TARGET_MACOS_NAME installer app found in /Applications"
    echo "   Checking for other macOS installers:"
    find /Applications -maxdepth 1 -type d -name "Install macOS*.app" | while read -r app; do
      echo "   • $(basename "$app")"
    done
  fi
fi

# Second, check if target update is available via softwareupdate
echo "🔍 CHECKING SOFTWARE UPDATE FOR $TARGET_MACOS_NAME"
softwareupdate_output=$(softwareupdate -l 2>&1)

if [[ "$TEST_MODE" == true ]]; then
  echo "Software Update output:"
  echo "$softwareupdate_output"
  echo ""
fi

# Look for target macOS in Software Update output
target_update=$(echo "$softwareupdate_output" | grep -i "macOS $TARGET_MACOS_NAME" | awk '{$1=$1};1')

if [[ "$TEST_MODE" == true ]]; then
  if [[ -n "$target_update" ]]; then
    echo "✅ Found $TARGET_MACOS_NAME update in Software Update:"
    echo "$target_update"

    # Try to find more details about the downloaded update
    echo "Checking /Library/Updates for downloaded packages:"
    if [[ -d "/Library/Updates" ]]; then
      find /Library/Updates -type d -name "*macOS*" -o -name "*$TARGET_MACOS_NAME*" | while read -r update_dir; do
        echo "   • $update_dir"
        find "$update_dir" -type f -name "*.pkg" | while read -r pkg; do
          echo "     - $(basename "$pkg") ($(du -sh "$pkg" | cut -f1))"
        done
      done
    fi
  else
    echo "❌ No macOS $TARGET_MACOS_NAME update found in Software Update"
  fi
fi

# Get the exact update label if target update is found
update_label=""
if [[ -n "$target_update" ]]; then
  # Extract the update label correctly by removing the "Label: " prefix
  update_label=$(echo "$softwareupdate_output" | grep -i "macOS $TARGET_MACOS_NAME" | grep "Label:" | sed 's/^* Label: //g' | awk '{$1=$1};1')

  if [[ "$TEST_MODE" == true ]]; then
    echo "📝 Update label: '$update_label'"
    if [[ -n "$update_label" ]]; then
      echo "Update command that would be executed:"
      echo "sudo softwareupdate --install \"$update_label\" --restart --no-scan --agree-to-license"
    else
      echo "⚠️ Could not determine the exact update label from Software Update output"
    fi
  fi
fi

# Now proceed with the actual logic
if [[ -n "$installer_app" ]]; then
  # Method 1: Use the full installer app if present
  send_embed "Major Upgrade" \
    "Found installer $(basename "$installer_app")—launching upgrade to macOS $TARGET_MACOS_NAME now (this will reboot)…" \
    10181046

  if [[ "$TEST_MODE" == true ]]; then
    echo "🔄 TEST MODE: Would execute the following command:"
    echo "sudo \"$installer_app/Contents/Resources/startosinstall\" --agreetolicense --nointeraction"
  else
    sudo "$installer_app/Contents/Resources/startosinstall" \
      --agreetolicense --nointeraction
  fi

  if [[ "$TEST_MODE" == true ]]; then
    echo "👋 TEST MODE: Script would exit here after launching the installer"
  else
    exit 0
  fi

elif [[ -n "$target_update" && -n "$update_label" ]]; then
  # Method 2: Use the already downloaded target update from Software Update
  send_embed "Major Upgrade" \
    "Found downloaded macOS $TARGET_MACOS_NAME update—installing now (this will reboot)…" \
    10181046

  send_embed "Installing macOS $TARGET_MACOS_NAME" "Installing update: $update_label" 10181046
  u0=$(date +%s)

  if [[ "$TEST_MODE" == true ]]; then
    echo "🔄 TEST MODE: Would execute the following command:"
    echo "sudo softwareupdate --install \"$update_label\" --restart --no-scan --agree-to-license"
  else
    # For both Apple Silicon and Intel Macs
    sudo softwareupdate --install "$update_label" --restart --no-scan --agree-to-license

    # Note: This might not execute if the update immediately restarts the Mac
    u1=$(date +%s)
    send_embed "macOS $TARGET_MACOS_NAME Installing" \
      "Installation started. Duration: $((u1-u0))s
      Your Mac will restart automatically to complete installation." \
      3066993
  fi

  if [[ "$TEST_MODE" == true ]]; then
    echo "👋 TEST MODE: Script would exit here after starting the update"
  else
    exit 0
  fi
elif [[ -n "$target_update" && -z "$update_label" ]]; then
  send_embed "Update Error" "Could not determine the exact update label for macOS $TARGET_MACOS_NAME. Falling back to normal updates." 15158332
  if [[ "$TEST_MODE" == true ]]; then
    echo "⚠️ TEST MODE: Could not determine the exact update label. Would fall back to normal updates."
  fi
fi

#–– 3) Minor/security updates if no major update was found or installed
send_embed "Listing Updates" "Running softwareupdate --list…" 15844367

if [[ "$TEST_MODE" == true ]]; then
  echo "🔍 TEST MODE: Available updates:"
  echo "$softwareupdate_output"
else
  updates=$(softwareupdate --list 2>&1)
  send_embed "Available Updates" \
    "$(echo -n "```"; echo; echo -n "$updates"; echo; echo -n "```")" \
    15105570

  send_embed "Installing Updates" "Installing all available updates…" 10181046
  u0=$(date +%s)
  sudo softwareupdate --install --all --restart
  u1=$(date +%s)

  # This might not execute if the update immediately restarts the Mac
  send_embed "Updates Installed" \
    "Duration: $((u1-u0))s
  Rebooting now…" \
    3066993
fi

#–– 4) reboot if not already triggered by the update
if [[ "$TEST_MODE" == true ]]; then
  echo "🔄 TEST MODE: Would restart the Mac here"
  echo "✅ Test completed successfully. Run without --test to perform the actual update."
else
  sudo shutdown -r now
fi