diff --git a/README.md b/README.md
index fed5a72..0a9f8e1 100644
--- a/README.md
+++ b/README.md
@@ -205,7 +205,7 @@ The setup process consists of two main phases:
 │   ├── formulae.txt           # Homebrew formulae list
 │   ├── casks.txt              # Homebrew casks list
 │   ├── logrotate.conf         # Log rotation configuration
-│   ├── iterm2.plist           # iTerm2 profile settings
+│   ├── com.googlecode.iterm2.plist           # iTerm2 profile settings
 │   └── Orangebrew.terminal    # Terminal.app profile
 └── docs/                       # Documentation
     ├── setup/                 # Setup documentation
diff --git a/app-setup/plex-setup.sh b/app-setup/plex-setup.sh
index 1de0b7a..81451d2 100755
--- a/app-setup/plex-setup.sh
+++ b/app-setup/plex-setup.sh
@@ -645,8 +645,8 @@ _try_ssh_host() {
 
   log "SSH connection details:"
   log "  Target host: '${host}'"
-  log "  SSH options: ConnectTimeout=5, BatchMode=yes"
-  log "  Command: ssh -o ConnectTimeout=5 -o BatchMode=yes '${host}' 'echo \"SSH_OK\"'"
+  log "  SSH options: StrictHostKeyChecking=no ConnectTimeout=5, BatchMode=yes"
+  log "  Command: ssh -o StrictHostKeyChecking=no -o ConnectTimeout=5 -o BatchMode=yes '${host}' 'echo \"SSH_OK\"'"
 
   # Test basic connectivity first
   log "Checking basic network connectivity to ${host}..."
@@ -659,7 +659,7 @@ _try_ssh_host() {
   # Test SSH with verbose output captured
   log "Attempting SSH connection with detailed diagnostics..."
   local ssh_output
-  ssh_output=$(ssh -o ConnectTimeout=5 -o BatchMode=yes -v "${host}" 'echo "SSH_OK"' 2>&1)
+  ssh_output=$(ssh -o StrictHostKeyChecking=no -o ConnectTimeout=5 -o BatchMode=yes -v "${host}" 'echo "SSH_OK"' 2>&1)
   local ssh_result=$?
 
   if [[ ${ssh_result} -eq 0 ]]; then
@@ -676,7 +676,7 @@ _try_ssh_host() {
     log "Additional SSH diagnostics:"
     ssh_version=$(ssh -V 2>&1)
     log "  SSH client version: ${ssh_version}"
-    log "  SSH config test: ssh -F /dev/null -o BatchMode=yes -o ConnectTimeout=5 '${host}' 'echo test' (would use system defaults)"
+    log "  SSH config test: ssh -F /dev/null -o BatchMode=yes -o StrictHostKeyChecking=no -o ConnectTimeout=5 '${host}' 'echo test' (would use system defaults)"
 
     return 1
   fi
@@ -1435,7 +1435,8 @@ main() {
           if test_ssh_connection "${MIGRATE_FROM}" true >/dev/null 2>&1; then
             log "Manual hostname resolved successfully"
           else
-            log "⚠️  Manual hostname resolution failed - will attempt migration anyway"
+            log "❌️ ${MIGRATE_FROM} hostname resolution failed"
+            return 1
           fi
         fi
       else
@@ -1444,7 +1445,8 @@ main() {
         if test_ssh_connection "${MIGRATE_FROM}" true >/dev/null 2>&1; then
           log "Manual hostname resolved successfully"
         else
-          log "⚠️  Manual hostname resolution failed - will attempt migration anyway"
+          log "❌️ ${MIGRATE_FROM} hostname resolution failed"
+          return 1
         fi
       fi
     else
diff --git a/app-setup/templates/mount-nas-media.sh b/app-setup/templates/mount-nas-media.sh
index dfec785..082b942 100755
--- a/app-setup/templates/mount-nas-media.sh
+++ b/app-setup/templates/mount-nas-media.sh
@@ -70,7 +70,7 @@ wait_for_network() {
 test_mount() {
   # Test basic mount verification using user-based pattern
   if ! mount | grep "${WHOAMI}" | grep -q "${PLEX_MEDIA_MOUNT}"; then
-    log "❌ Mount not visible in system mount table for user ${WHOAMI}"
+    log "⚠️ Mount not visible in system mount table for user ${WHOAMI}"
     return 1
   fi
   log "✅ Mount verification successful (active mount found for ${WHOAMI})"
diff --git a/docs/apps/plex-setup-README.md b/docs/apps/plex-setup-README.md
index d2ca850..4853f95 100644
--- a/docs/apps/plex-setup-README.md
+++ b/docs/apps/plex-setup-README.md
@@ -112,6 +112,22 @@ rsync -av --exclude='Cache' "~/Library/Application Support/Plex Media Server/" ~
 
 The script supports both local migration (files in `~/plex-migration/`) and remote migration via SSH.
 
+### SSH Security for Migration
+
+**SSH Host Key Verification**: For automated migration workflows, the script uses `StrictHostKeyChecking=no` to prevent blocking on unknown host keys during server-to-server transfers. This is intentional for migration scenarios where:
+
+- Target server may not have established SSH relationships with source servers
+- Migration typically occurs between trusted servers on the same network
+- Automation workflows need to proceed without manual intervention for host key acceptance
+
+**Security Context**: This setting is used specifically for:
+
+- Migration connection testing: `ssh -o StrictHostKeyChecking=no -o ConnectTimeout=5 -o BatchMode=yes`
+- Automated file transfers during configuration migration
+- One-time setup operations between known server pairs
+
+**Note**: This does not affect ongoing SSH security for regular server operations, which continue to use standard SSH host key verification.
+
 ### Post-Migration: Home Screen Setup
 
 **⚠️ Important**: After migrating from an existing Plex server, you may need to re-pin your media sources to the home screen.
diff --git a/docs/operator.md b/docs/operator.md
index 36a99a6..a48476c 100644
--- a/docs/operator.md
+++ b/docs/operator.md
@@ -12,6 +12,8 @@ The system is configured to automatically log in as the operator user after rebo
 - **Desktop with clean dock** (iTerm, Plex, essential apps)
 - **Fast User Switching menu** in the menu bar (showing current user)
 
+> **📋 First Login Dialogs**: On first operator login, you may encounter Apple Setup Assistant dialogs. For guidance on handling these, see [Apple First-Boot Dialog Guide](setup/apple-first-boot-dialogs.md#operator-account-first-login)
+
 ## Automatic Setup
 
 ### 1. First-Login Customization
diff --git a/docs/setup/apple-first-boot-dialogs.md b/docs/setup/apple-first-boot-dialogs.md
new file mode 100644
index 0000000..ba5c91c
--- /dev/null
+++ b/docs/setup/apple-first-boot-dialogs.md
@@ -0,0 +1,197 @@
+# Apple First-Boot Dialog Guide
+
+This guide provides step-by-step instructions for navigating Apple's Setup Assistant dialogs during initial Mac Mini configuration and operator account first login.
+
+## Admin Account Setup (Initial macOS Installation)
+
+When setting up the Mac Mini for the first time, you'll encounter these Apple dialogs in sequence:
+
+### 1. Language Selection
+
+- **Action**: Select your preferred language
+- **Recommendation**: Choose your primary language
+
+### 2. Region Selection
+
+- **Action**: Select your country/region
+- **Recommendation**: Choose your current location for proper timezone and regional settings
+
+### 3. Data Transfer & Migration
+
+- **Action**: Choose transfer method
+- **Options**:
+  - **iPhone/iPad Transfer** ✅ Recommended if available (requires iOS device with backup)
+  - **Time Machine Backup** (if you have an existing backup)
+  - **Don't transfer any information now** (manual setup)
+- **Note**: iPhone/iPad transfer can pre-configure WiFi, Apple ID, and other settings
+
+### 4. Accessibility
+
+- **Action**: Configure accessibility options
+- **Recommendation**: Configure as needed for your requirements, or skip if not needed
+
+### 5. Data & Privacy
+
+- **Action**: Review Apple's privacy policy
+- **Recommendation**: Continue after reading
+
+### 6. Create Administrator Account
+
+- **Full Name**: Will be pre-populated if you used iPhone/iPad transfer
+- **Account Name**: Will be pre-populated if you used iPhone/iPad transfer
+- **Password**: Create a strong password (you'll use this for first-boot setup)
+- **Hint**: Optional password hint
+
+### 7. Apple Account Configuration
+
+#### 7.1 Terms & Conditions
+
+- **Action**: Agree to Apple's Terms and Conditions
+- **Recommendation**: Review and agree
+
+#### 7.2 Customize Settings
+
+##### 7.2.1 Location Services
+
+- **Action**: Enable or disable location services
+- **Recommendation**: Enable for timezone and system functionality
+
+##### 7.2.2 Analytics & Improvement
+
+- **Action**: Choose whether to share analytics with Apple
+- **Recommendation**: Configure based on your privacy preferences
+
+##### 7.2.3 Screen Time
+
+- **Action**: Set up Screen Time monitoring
+- **Recommendation**: Skip for server setup
+
+##### 7.2.4 Apple Intelligence
+
+- **Action**: Configure Apple's AI features
+- **Recommendation**: Configure based on your preferences
+
+##### 7.2.5 FileVault Disk Encryption
+
+- **Action**: Choose whether to enable FileVault
+- **⚠️ CRITICAL**: **Turn OFF FileVault!**
+- **Reason**: FileVault prevents automatic login for the operator account
+- **Note**: This is essential for proper server operation
+
+##### 7.2.6 Touch ID
+
+- **Action**: Set up Touch ID fingerprint authentication
+- **Recommendation**: Set up for convenient sudo access during administration
+
+##### 7.2.7 Apple Pay
+
+- **Action**: Set up Apple Pay
+- **Recommendation**: Configure based on your preferences
+
+##### 7.2.8 Choose Your Look
+
+- **Action**: Select Light, Dark, or Auto appearance
+- **Recommendation**: Auto (adapts to time of day)
+
+##### 7.2.9 Software Updates
+
+- **Action**: Configure automatic update preferences
+- **Recommendation**: Enable automatic security updates, manual for system updates
+
+### 8. Continue Setup
+
+- **Action**: Complete the setup process
+- **Result**: Proceed to desktop
+
+### 9. Desktop
+
+- **Result**: macOS setup complete, ready for first-boot script execution
+
+---
+
+## Operator Account First Login
+
+When the operator account logs in for the first time, they'll encounter a simplified Setup Assistant:
+
+### 1. Accessibility
+
+- **Action**: Configure accessibility options
+- **Recommendation**: Configure as needed, or skip if not required
+
+### 2. Apple Account
+
+- **Action**: Sign in with Apple ID
+- **⚠️ RECOMMENDATION**: **Skip this step**
+- **Reason**: Server operations don't require operator Apple ID integration
+- **Note**: You can always add this later if needed
+
+### 3. Find My
+
+- **Action**: Enable Find My for the device
+- **Recommendation**: Configure based on your security preferences
+
+### 4. Analytics & Improvement
+
+- **Action**: Choose analytics sharing preferences
+- **Recommendation**: Configure based on privacy preferences
+
+### 5. Screen Time
+
+- **Action**: Set up Screen Time
+- **⚠️ RECOMMENDATION**: **Skip this step**
+- **Reason**: Not relevant for server operation
+
+### 6. Apple Intelligence
+
+- **Action**: Configure Apple AI features
+- **⚠️ RECOMMENDATION**: **Skip this step**
+- **Reason**: Not needed for server operation, may impact performance
+
+### 7. Touch ID Setup Assistant
+
+- **Action**: Set up Touch ID
+- **⚠️ RECOMMENDATION**: **Cancel/Skip this step**
+- **Reason**: Operator account uses automatic login, Touch ID not typically needed
+
+### 8. Choose Your Look
+
+- **Action**: Select appearance theme
+- **Recommendation**: Auto or user preference
+
+### 9. Continue
+
+- **Action**: Complete operator setup
+- **Result**: Proceed to desktop
+
+### 10. Desktop
+
+- **Result**: Operator account setup complete, automatic application launch will begin
+
+---
+
+## Important Notes
+
+### FileVault Warning
+
+**CRITICAL**: Ensure FileVault is disabled during admin account setup. FileVault encryption prevents the automatic login functionality required for proper server operation.
+
+### Account Purpose
+
+- **Admin Account**: Used for system administration, setup, and maintenance
+- **Operator Account**: Used for day-to-day server operation and automatic application launch
+
+### Setup Timing
+
+- Complete Apple dialogs **before** running `first-boot.sh`
+- Operator dialogs appear automatically on first operator login after reboot
+
+### Migration Assistant Benefits
+
+Using iPhone/iPad transfer during initial setup can significantly reduce manual configuration by pre-populating:
+
+- WiFi network settings
+- Apple ID information
+- Basic user account details
+- System preferences
+
+This reduces the overall setup time and ensures consistent configuration across your devices.
diff --git a/docs/setup/first-boot.md b/docs/setup/first-boot.md
index 7de63d9..2621066 100644
--- a/docs/setup/first-boot.md
+++ b/docs/setup/first-boot.md
@@ -16,6 +16,8 @@ The `first-boot.sh` script performs complete automated setup of your Mac Mini se
 5. **Reach the desktop** before proceeding
 6. **Enable AirDrop:** Press Cmd-Shift-R to open AirDrop, and select "Allow me to be discovered by: Everyone"
 
+> **📋 Detailed Setup Guide**: For step-by-step instructions on navigating Apple's Setup Assistant dialogs, see [Apple First-Boot Dialog Guide](apple-first-boot-dialogs.md)
+
 ### Transfer Setup Files
 
 1. **AirDrop the complete macmini-setup folder** from your development Mac
@@ -297,3 +299,43 @@ After successful first boot setup:
 4. **Run application setup scripts** in `~/app-setup/`
 
 The Mac Mini is now ready for native application deployment and service configuration.
+
+## Post-Setup Configuration
+
+### Safari Extension Syncing
+
+To sync Safari extensions across your devices (iPhone, iPad, Mac), enable extension syncing:
+
+1. **Open System Settings** → **Apple ID** → **iCloud**
+2. **Enable Safari syncing** if not already enabled
+3. **In Safari**: Go to **Safari** → **Settings** → **Extensions**
+4. **Enable "Sync Safari Extensions"** to share extensions across all your devices
+
+This ensures your Safari extensions are available on your Mac Mini server when accessing web interfaces for applications like Plex, Transmission, or other web-based management tools.
+
+**Reference**: [Safari Extension Syncing Guide](https://ios.gadgethacks.com/how-to/safari-now-lets-you-sync-and-manage-all-your-web-extensions-across-your-iphone-ipad-and-mac-0385127/)
+
+## Known Issues
+
+The following issues are known limitations of the current setup system:
+
+### Terminal Profiles
+
+**iTerm2 Profile Syncing**: iTerm2 profiles do not sync properly during automated setup. The profile files are copied correctly, but iTerm2 may not recognize or apply the imported settings immediately.
+
+**Workaround**:
+
+* Manually import profiles via iTerm2 → **Preferences** → **Profiles** → **Other Actions** → **Import JSON Profiles**
+* Or restart iTerm2 multiple times until profiles are recognized
+
+### System Notifications
+
+**Background Item Notifications**: macOS generates numerous "background item added" notifications during Homebrew package installation and application setup. These notifications cannot be automatically suppressed by the setup scripts.
+
+**Impact**:
+
+* Users will see multiple system notifications during setup
+* Notifications are informational and do not affect setup functionality
+* No user action required - notifications will clear automatically
+
+**Future Improvement**: Apple does not currently provide an API to suppress these notifications during automated setup processes.
diff --git a/docs/setup/prep-airdrop.md b/docs/setup/prep-airdrop.md
index 05dc2fa..3c31163 100644
--- a/docs/setup/prep-airdrop.md
+++ b/docs/setup/prep-airdrop.md
@@ -106,7 +106,7 @@ macmini-setup/
 │   ├── config.conf              # Server settings
 │   ├── dev_fingerprint.conf     # Safety check data
 │   ├── formulae.txt             # Homebrew packages
-│   ├── iterm2.plist             # iTerm2 profile/settings (optional)
+│   ├── com.googlecode.iterm2.plist             # iTerm2 profile/settings (optional)
 │   ├── keychain_manifest.conf   # Keychain service identifiers
 │   ├── logrotate.conf
 │   ├── mac-server-setup-db      # External keychain file
diff --git a/prep-airdrop.sh b/prep-airdrop.sh
index bc69832..9f38ada 100755
--- a/prep-airdrop.sh
+++ b/prep-airdrop.sh
@@ -831,12 +831,7 @@ if [[ -d "${SCRIPT_SOURCE_DIR}" ]]; then
   if [[ "${USE_ITERM2:-false}" == "true" ]]; then
     if command -v it2check >/dev/null 2>&1; then
       echo "Exporting iTerm2 preferences..."
-      if defaults export com.googlecode.iterm2 "${OUTPUT_PATH}/config/iterm2.plist"; then
-        add_to_manifest "config/iterm2.plist" "OPTIONAL"
-        echo "iTerm2 preferences exported to deployment package"
-      else
-        echo "Warning: Failed to export iTerm2 preferences"
-      fi
+      copy_with_manifest "${HOME}/Library/Preferences/com.googlecode.iterm2.plist" "config/com.googlecode.iterm2.plist" "OPTIONAL"
     else
       echo "Warning: USE_ITERM2 is enabled but iTerm2 is not installed (it2check not found)"
     fi
@@ -890,6 +885,10 @@ chmod -R 755 "${OUTPUT_PATH}/app-setup"
 chmod 600 "${OUTPUT_PATH}/config/"* 2>/dev/null || true
 chmod 600 "${OUTPUT_PATH}/app-setup/config/"* 2>/dev/null || true
 
+# Ensure all shell scripts are executable
+echo "Making all shell scripts executable..."
+find "${OUTPUT_PATH}" -name '*.sh' -exec chmod -v a+rx {} \;
+
 # Create Keychain manifest for server-side credential access
 create_keychain_manifest
 
diff --git a/scripts/server/first-boot.sh b/scripts/server/first-boot.sh
index 1a1fe3e..341e0ab 100755
--- a/scripts/server/first-boot.sh
+++ b/scripts/server/first-boot.sh
@@ -751,34 +751,6 @@ mkdir -p "${LOG_DIR}"
 touch "${LOG_FILE}"
 chmod 600 "${LOG_FILE}"
 
-# Function to check if a Terminal window with specific title exists
-check_terminal_window_exists() {
-  local window_title="$1"
-  osascript -e "
-    tell application \"Terminal\"
-      set window_exists to false
-      try
-        repeat with w in windows
-          if (name of w) contains \"${window_title}\" then
-            set window_exists to true
-            exit repeat
-          end if
-        end repeat
-      end try
-      return window_exists
-    end tell
-  " 2>/dev/null
-}
-
-# Tail log in separate window (only if one doesn't already exist)
-window_exists=$(check_terminal_window_exists "Setup Log")
-if [[ "${window_exists}" == "true" ]]; then
-  log "Found existing Setup Log window - reusing it"
-else
-  log "Opening new Setup Log window"
-  osascript -e 'tell application "Terminal" to do script "printf \"\\e]0;Setup Log\\a\"; tail -F '"${LOG_FILE}"'"' || echo "oops, no tail"
-fi
-
 # Print header
 set_section "Starting Mac Mini '${SERVER_NAME}' Server Setup"
 log "Running as user: ${ADMIN_USERNAME}"
diff --git a/scripts/server/operator-first-login.sh b/scripts/server/operator-first-login.sh
index c30fa6c..c7c1eda 100755
--- a/scripts/server/operator-first-login.sh
+++ b/scripts/server/operator-first-login.sh
@@ -260,46 +260,10 @@ setup_terminal_profile() {
 # Task: Configure iTerm2 preferences
 setup_iterm2_preferences() {
   progress "Setting up iTerm2 preferences..."
-
-  local iterm2_config_dir="${HOME}/.config/iterm2"
-  local preferences_file="${iterm2_config_dir}/iterm2.plist"
-
-  # Check if preferences file exists
-  if [[ ! -f "${preferences_file}" ]]; then
-    progress "No iTerm2 preferences found at ${preferences_file} - skipping iTerm2 setup"
-    return 0
-  fi
-
-  # Check if iTerm2 is installed (more reliable detection method)
-  if [[ ! -d /Applications/iTerm.app ]]; then
-    progress "iTerm2 not installed - skipping preferences import"
-    return 0
-  fi
-
-  progress "Importing iTerm2 preferences..."
-
-  # Ensure iTerm2 is not running during import for better reliability
-  if pgrep -f "iTerm.app" >/dev/null 2>&1; then
-    progress "iTerm2 is currently running - preferences import may not take effect until restart"
-  fi
-
-  # Import preferences using defaults import
-  if defaults import com.googlecode.iterm2 "${preferences_file}"; then
-    progress "iTerm2 preferences import command succeeded"
-
-    # Verify that import actually worked by checking for a key preference
-    if defaults read com.googlecode.iterm2 "Default Bookmark Guid" >/dev/null 2>&1; then
-      progress "✅ Successfully imported and verified iTerm2 preferences"
-      progress "Preferences will be active when iTerm2 is next launched"
-    else
-      progress "⚠️ Import command succeeded but preferences verification failed"
-      progress "iTerm2 preferences may not have been properly imported"
-    fi
-  else
-    progress "❌ Failed to import iTerm2 preferences"
-    progress "Check that preferences file is valid: ${preferences_file}"
-    progress "You can manually import by opening iTerm2 > Preferences > Profiles > Other Actions > Import JSON Profiles"
-  fi
+  killall iTerm2 &>/dev/null || true
+  open -a iTerm2 &>/dev/null || true
+  killall iTerm2 &>/dev/null || true
+  progress "Imported iTerm2 preferences"
 }
 
 # Task: Start logrotate service
diff --git a/scripts/server/setup-application-preparation.sh b/scripts/server/setup-application-preparation.sh
old mode 100644
new mode 100755
diff --git a/scripts/server/setup-command-line-tools.sh b/scripts/server/setup-command-line-tools.sh
old mode 100644
new mode 100755
index 314d31a..e1ecab0
--- a/scripts/server/setup-command-line-tools.sh
+++ b/scripts/server/setup-command-line-tools.sh
@@ -229,8 +229,8 @@ ENHANCED_MONITOR_EOF
     done
 
     # Stop monitoring and cleanup (suppress job termination messages)
-    (kill "${monitor_pid}" && wait "${monitor_pid}") 2>/dev/null || true
-    rm -f "${monitor_script}" 2>/dev/null || true
+    (kill "${monitor_pid}" && wait "${monitor_pid}") &>/dev/null || true
+    rm -f "${monitor_script}" &>/dev/null || true
 
     # Wait for the install process to fully complete
     if kill -0 "${install_pid}" 2>/dev/null; then
diff --git a/scripts/server/setup-dock-configuration.sh b/scripts/server/setup-dock-configuration.sh
index 31cb5ee..825ca97 100755
--- a/scripts/server/setup-dock-configuration.sh
+++ b/scripts/server/setup-dock-configuration.sh
@@ -42,6 +42,12 @@ else
   exit 1
 fi
 
+# HOMEBREW_PREFIX is set and exported by first-boot.sh based on architecture
+if [[ -z "${HOMEBREW_PREFIX:-}" ]]; then
+  echo "Error: HOMEBREW_PREFIX not set - this script must be run from first-boot.sh"
+  exit 1
+fi
+
 # Set derived variables
 HOSTNAME="${HOSTNAME_OVERRIDE:-${SERVER_NAME}}"
 HOSTNAME_LOWER="$(tr '[:upper:]' '[:lower:]' <<<"${HOSTNAME}")"
@@ -134,42 +140,56 @@ check_success() {
   fi
 }
 
+# Make sure dockutil is installed
+check_dockutil() {
+  if command -v dockutil; then
+    # installed and in path, all good!
+    return 0
+  elif [[ -f "${HOMEBREW_PREFIX}/bin/dockutil" ]]; then
+    # installed but not in path
+    export PATH="${PATH}:${HOMEBREW_PREFIX}/bin"
+    command -v dockutil || return 1
+  else
+    # not installed
+    "${HOMEBREW_PREFIX}/bin/brew" install dockutil
+    export PATH="${PATH}:${HOMEBREW_PREFIX}/bin"
+    command -v dockutil || return 1
+  fi
+}
+
 # Main dock configuration function
 configure_dock() {
   set_section "Cleaning up Administrator Dock"
 
   log "Cleaning up Administrator Dock"
 
-  if command -v dockutil &>/dev/null; then
-    dockutil \
-      --remove Messages \
-      --remove Mail \
-      --remove Maps \
-      --remove Photos \
-      --remove FaceTime \
-      --remove Calendar \
-      --remove Contacts \
-      --remove Reminders \
-      --remove Freeform \
-      --remove TV \
-      --remove Music \
-      --remove News \
-      --remove 'iPhone Mirroring' \
-      --remove /System/Applications/Utilities/Terminal.app \
-      --add /Applications/iTerm.app \
-      --add /System/Applications/Passwords.app \
-      --allhomes \
-      &>/dev/null || true
-    check_success "Administrator Dock cleaned up"
-  else
-    log "Could not locate dockutil"
-  fi
+  dockutil \
+    --remove Messages \
+    --remove Mail \
+    --remove Maps \
+    --remove Photos \
+    --remove FaceTime \
+    --remove Calendar \
+    --remove Contacts \
+    --remove Reminders \
+    --remove Freeform \
+    --remove TV \
+    --remove Music \
+    --remove News \
+    --remove 'iPhone Mirroring' \
+    --remove /System/Applications/Utilities/Terminal.app \
+    --add /Applications/iTerm.app \
+    --add /System/Applications/Passwords.app \
+    --allhomes \
+    &>/dev/null || true
+  check_success "Administrator Dock cleaned up"
 }
 
 # Main execution
 main() {
   log "Starting dock configuration module"
 
+  check_dockutil
   configure_dock
 
   # Simple completion message
diff --git a/scripts/server/setup-package-installation.sh b/scripts/server/setup-package-installation.sh
index 34b1b4e..3ba1995 100755
--- a/scripts/server/setup-package-installation.sh
+++ b/scripts/server/setup-package-installation.sh
@@ -241,30 +241,52 @@ if [[ "${SKIP_PACKAGES}" = false ]]; then
 
   # Function to install formulae if not already installed
   install_formula() {
-    if ! "${HOMEBREW_PREFIX}/bin/brew" list "$1" &>/dev/null; then
-      log "Installing formula: $1"
-      if "${HOMEBREW_PREFIX}/bin/brew" install "$1"; then
-        log "✅ Formula installation: $1"
+    local formula="$1"
+    local current_count="$2"
+    local total_count="$3"
+
+    if ! "${HOMEBREW_PREFIX}/bin/brew" list "${formula}" &>/dev/null; then
+      show_log -n "Installing formulae... (${current_count}/${total_count}) ${formula}... "
+      if "${HOMEBREW_PREFIX}/bin/brew" install "${formula}" &>/dev/null; then
+        show_log "✅"
+        log "✅ Formula installation: ${formula}"
       else
-        collect_error "Formula installation failed: $1"
+        show_log "❌"
+        collect_error "Formula installation failed: ${formula}"
         # Continue instead of exiting
       fi
     else
-      log "Formula already installed: $1"
+      show_log "Installing formulae... (${current_count}/${total_count}) ${formula} (already installed) ✅"
+      log "Formula already installed: ${formula}"
     fi
   }
 
   # Function to install casks if not already installed
   install_cask() {
-    if ! "${HOMEBREW_PREFIX}/bin/brew" list --cask "$1" &>/dev/null; then
-      log "Installing cask: $1"
+    local cask="$1"
+    local current_count="$2"
+    local total_count="$3"
+
+    # Get estimated size for large packages
+    local size_hint=""
+    case "${cask}" in
+      plex-media-server) size_hint=" (~250 MB)" ;;
+      filebot) size_hint=" (~50 MB)" ;;
+      vlc) size_hint=" (~75 MB)" ;;
+      bbedit) size_hint=" (~25 MB)" ;;
+      *) size_hint="" ;;
+    esac
+
+    if ! "${HOMEBREW_PREFIX}/bin/brew" list --cask "${cask}" &>/dev/null; then
+      show_log -n "Installing casks... (${current_count}/${total_count}) ${cask}${size_hint}... "
 
       # Capture /Applications before installation
       local before_apps
       before_apps=$(find /Applications -maxdepth 1 -type d -name "*.app" 2>/dev/null | sort)
 
-      if "${HOMEBREW_PREFIX}/bin/brew" install --cask "$1"; then
-        log "✅ Cask installation: $1"
+      if "${HOMEBREW_PREFIX}/bin/brew" install --cask "${cask}" &>/dev/null; then
+        show_log "✅"
+        log "✅ Cask installation: ${cask}"
 
         # Capture /Applications after installation
         local after_apps
@@ -283,17 +305,18 @@ if [[ "${SKIP_PACKAGES}" = false ]]; then
           done <<<"${new_apps}"
         fi
       else
-        collect_error "Cask installation failed: $1"
+        show_log "❌"
+        collect_error "Cask installation failed: ${cask}"
         # Continue instead of exiting
       fi
     else
-      log "Cask already installed: $1"
+      show_log "Installing casks... (${current_count}/${total_count}) ${cask} (already installed) ✅"
+      log "Cask already installed: ${cask}"
     fi
   }
 
   # Install formulae from list
   if [[ -f "${FORMULAE_FILE}" ]]; then
-    show_log "Installing formulae from ${FORMULAE_FILE}"
     formulae=()
     if [[ -f "${FORMULAE_FILE}" ]]; then
       while IFS= read -r line; do
@@ -302,8 +325,14 @@ if [[ "${SKIP_PACKAGES}" = false ]]; then
         fi
       done <"${FORMULAE_FILE}"
     fi
+
+    formulae_count=${#formulae[@]}
+    show_log "Installing ${formulae_count} formulae from ${FORMULAE_FILE}"
+
+    current=1
     for formula in "${formulae[@]}"; do
-      install_formula "${formula}"
+      install_formula "${formula}" "${current}" "${formulae_count}"
+      ((current += 1))
     done
   else
     log "Formulae list not found, skipping formula installations"
@@ -311,7 +340,6 @@ if [[ "${SKIP_PACKAGES}" = false ]]; then
 
   # Install casks from list
   if [[ -f "${CASKS_FILE}" ]]; then
-    show_log "Installing casks from ${CASKS_FILE}"
     casks=()
     if [[ -f "${CASKS_FILE}" ]]; then
       while IFS= read -r line; do
@@ -320,24 +348,39 @@ if [[ "${SKIP_PACKAGES}" = false ]]; then
         fi
       done <"${CASKS_FILE}"
     fi
+
+    casks_count=${#casks[@]}
+    show_log "Installing ${casks_count} casks from ${CASKS_FILE}"
+
+    current=1
     for cask in "${casks[@]}"; do
-      install_cask "${cask}"
+      install_cask "${cask}" "${current}" "${casks_count}"
+      ((current += 1))
     done
   else
     log "Casks list not found, skipping cask installations"
   fi
 
   # Cleanup after installation
-  log "Cleaning up Homebrew files"
-  "${HOMEBREW_PREFIX}/bin/brew" cleanup
-  check_success "Homebrew cleanup"
+  show_log -n "Cleaning up Homebrew files... "
+  if "${HOMEBREW_PREFIX}/bin/brew" cleanup &>/dev/null; then
+    show_log "✅"
+    log "✅ Homebrew cleanup completed"
+  else
+    show_log "⚠️"
+    log "⚠️ Homebrew cleanup had warnings"
+  fi
 
   # Run brew doctor and save output
-  log "Running brew doctor diagnostic"
+  show_log -n "Running Homebrew diagnostic... "
   BREW_DOCTOR_OUTPUT="${LOG_DIR}/brew-doctor-$(date +%Y%m%d-%H%M%S).log"
-  "${HOMEBREW_PREFIX}/bin/brew" doctor >"${BREW_DOCTOR_OUTPUT}" 2>&1 || true
-  log "Brew doctor output saved to: ${BREW_DOCTOR_OUTPUT}"
-  check_success "Brew doctor diagnostic"
+  if "${HOMEBREW_PREFIX}/bin/brew" doctor >"${BREW_DOCTOR_OUTPUT}" 2>&1; then
+    show_log "✅"
+    log "✅ Brew doctor diagnostic completed successfully"
+  else
+    show_log "⚠️"
+    log "⚠️ Brew doctor found issues - check ${BREW_DOCTOR_OUTPUT}"
+  fi
 
 fi
 
diff --git a/scripts/server/setup-terminal-profiles.sh b/scripts/server/setup-terminal-profiles.sh
index 6f44397..6c34213 100755
--- a/scripts/server/setup-terminal-profiles.sh
+++ b/scripts/server/setup-terminal-profiles.sh
@@ -147,7 +147,7 @@ else
 fi
 
 # iTerm2 preferences path (exported plist file)
-ITERM2_PREFERENCES_PATH="${SETUP_DIR}/config/iterm2.plist"
+ITERM2_PREFERENCES_PATH="${SETUP_DIR}/config/com.googlecode.iterm2.plist"
 
 # Backup preferences for a user
 backup_user_preferences() {
@@ -185,6 +185,8 @@ import_terminal_profile_for_user() {
     return 1
   fi
 
+  xattr -d com.apple.quarantine "${profile_file}" 2>/dev/null || true
+
   # Extract profile name from the plist
   local profile_name
   if ! profile_name=$(plutil -extract name raw "${profile_file}" 2>/dev/null); then
@@ -196,15 +198,66 @@ import_terminal_profile_for_user() {
 
   if [[ "${username}" == "${ADMIN_USERNAME}" ]]; then
     # Import for current admin user - direct registration
-    if open "${profile_file}"; then
+    log "Opening Terminal profile to import settings..."
+
+    # Use AppleScript to track window IDs and close only the newly created window
+    local applescript_result
+    applescript_result=$(osascript -e "
+tell application \"Terminal\"
+    -- Get list of existing window IDs before opening profile
+    set existing_window_ids to {}
+    repeat with w in windows
+        set existing_window_ids to existing_window_ids & {id of w}
+    end repeat
+
+    -- Open the profile file (this will create a new window)
+    open POSIX file \"${profile_file}\" as alias
+
+    -- Wait for new window to appear (max 5 seconds)
+    set wait_count to 0
+    repeat while wait_count < 10
+        delay 0.5
+        set wait_count to wait_count + 1
+
+        -- Check if we have a new window
+        repeat with w in windows
+            if (id of w) is not in existing_window_ids then
+                -- Found the new window - close it and exit
+                close w
+                return \"success\"
+            end if
+        end repeat
+    end repeat
+
+    return \"timeout\"
+end tell
+")
+
+    if [[ "${applescript_result}" == "success" ]]; then
+      log "Successfully imported Terminal profile and closed temporary window"
+
       # Set as default and startup profile
       defaults write com.apple.Terminal "Default Window Settings" -string "${profile_name}"
       defaults write com.apple.Terminal "Startup Window Settings" -string "${profile_name}"
+
+      local new_default
+      new_default=$(defaults read com.apple.Terminal "Default Window Settings")
+      if [[ ${new_default} != "${profile_name}" ]]; then
+        collect_error "Failed to set ${profile_name} as Default profile for ${username}"
+      fi
+
+      local new_startup
+      new_startup=$(defaults read com.apple.Terminal "Startup Window Settings")
+      if [[ ${new_startup} != "${profile_name}" ]]; then
+        collect_error "Failed to set ${profile_name} as Startup profile for ${username}"
+      fi
+
       log "Successfully imported Terminal profile for ${username}"
       log "New profile will be active in next Terminal session"
       return 0
     else
-      collect_error "Failed to open Terminal profile file for ${username}"
+      log "AppleScript window management failed: ${applescript_result}"
+      collect_error "Failed to import Terminal profile for ${username} - window management issue"
       return 1
     fi
   else
@@ -253,8 +306,13 @@ import_iterm2_preferences_for_user() {
   fi
 
   if [[ "${username}" == "${ADMIN_USERNAME}" ]]; then
-    # Import for current admin user - direct import
-    if defaults import com.googlecode.iterm2 "${preferences_file}"; then
+    # Import for current admin user - file copy
+    if cp -f "${preferences_file}" "${HOME}/Library/Preferences"; then
+      killall iTerm2 &>/dev/null || true
+      sleep 1
+      open -a iTerm2 &>/dev/null || true
+      sleep 1
+      killall iTerm2 &>/dev/null || true
       log "Successfully imported iTerm2 preferences for ${username}"
       log "Restart iTerm2 to see changes"
       return 0
@@ -266,20 +324,23 @@ import_iterm2_preferences_for_user() {
     # For operator user - copy preferences file to their config directory
     # Import will happen during operator-first-login.sh
     local operator_home="/Users/${username}"
-    local operator_config_dir="${operator_home}/.config/iterm2"
-    local operator_preferences_file
-    operator_preferences_file="${operator_config_dir}/$(basename "${preferences_file}")"
+    local operator_library_prefs_dir="${operator_home}/Library/Preferences"
 
     # Create config directory with proper ownership
-    if ! sudo -iu "${username}" mkdir -p "${operator_config_dir}"; then
+    if ! sudo -iu "${username}" mkdir -p "${operator_library_prefs_dir}"; then
       collect_error "Failed to create iTerm2 config directory for ${username}"
       return 1
     fi
 
     # Copy preferences file to operator's config directory
-    if sudo cp "${preferences_file}" "${operator_preferences_file}" \
-      && sudo chown "${username}:staff" "${operator_preferences_file}"; then
-      log "Successfully copied iTerm2 preferences to ${operator_preferences_file}"
+    if sudo cp "${preferences_file}" "${operator_library_prefs_dir}" \
+      && sudo chown "${username}:staff" "${operator_library_prefs_dir}/${preferences_file}"; then
+      sudo -iu "{username}" killall iTerm2 &>/dev/null || true
+      sleep 1
+      sudo -iu "{username}" open -a iTerm2 &>/dev/null || true
+      sleep 1
+      sudo -iu "{username}" killall iTerm2 &>/dev/null || true
+      log "Successfully copied iTerm2 preferences to ${operator_library_prefs_dir}"
       log "Preferences will be imported during operator first login"
       return 0
     else
@@ -308,6 +369,20 @@ check_running_terminal_apps() {
   fi
 }
 
+# Function to handle optional operations gracefully
+check_optional_success() {
+  local exit_code="$1"
+  local operation_name="$2"
+  if [[ ${exit_code} -eq 0 ]]; then
+    show_log "✅ ${operation_name}"
+    log "✅ ${operation_name}"
+  else
+    show_log "⚠️  ${operation_name} failed (optional feature - continuing)"
+    log "⚠️  ${operation_name} failed (optional feature - continuing)"
+    # Don't use collect_error since this is optional and shouldn't block setup
+  fi
+}
+
 # Main terminal profile configuration function
 configure_terminal_profiles() {
   set_section "Configuring Terminal Profiles"
@@ -329,14 +404,14 @@ configure_terminal_profiles() {
   if [[ -n "${TERMINAL_PROFILE_PATH}" ]] && [[ -f "${TERMINAL_PROFILE_PATH}" ]]; then
     log "Importing Terminal profiles..."
     import_terminal_profile_for_user "${ADMIN_USERNAME}" "${TERMINAL_PROFILE_PATH}"
-    check_success "Terminal profile import for admin user"
+    check_optional_success $? "Terminal profile import for admin user"
 
     if dscl . -list /Users 2>/dev/null | grep -q "^${OPERATOR_USERNAME}$"; then
       import_terminal_profile_for_user "${OPERATOR_USERNAME}" "${TERMINAL_PROFILE_PATH}"
-      check_success "Terminal profile import for operator user"
+      check_optional_success $? "Terminal profile import for operator user"
     fi
   elif [[ -n "${TERMINAL_PROFILE_PATH}" ]]; then
-    log "Terminal profile file not found: ${TERMINAL_PROFILE_PATH}"
+    log "⚠️  Terminal profile file not found: ${TERMINAL_PROFILE_PATH} (optional feature - continuing)"
   else
     log "No Terminal profile configured - skipping Terminal profile setup"
   fi
@@ -345,14 +420,14 @@ configure_terminal_profiles() {
   if [[ "${USE_ITERM2:-false}" == "true" ]] && [[ -f "${ITERM2_PREFERENCES_PATH}" ]]; then
     log "Importing iTerm2 preferences..."
     import_iterm2_preferences_for_user "${ADMIN_USERNAME}" "${ITERM2_PREFERENCES_PATH}"
-    check_success "iTerm2 preferences import for admin user"
+    check_optional_success $? "iTerm2 preferences import for admin user"
 
     if dscl . -list /Users 2>/dev/null | grep -q "^${OPERATOR_USERNAME}$"; then
       import_iterm2_preferences_for_user "${OPERATOR_USERNAME}" "${ITERM2_PREFERENCES_PATH}"
-      check_success "iTerm2 preferences import for operator user"
+      check_optional_success $? "iTerm2 preferences import for operator user"
     fi
   elif [[ "${USE_ITERM2:-false}" == "true" ]] && [[ ! -f "${ITERM2_PREFERENCES_PATH}" ]]; then
-    log "iTerm2 preferences file not found: ${ITERM2_PREFERENCES_PATH}"
+    log "⚠️  iTerm2 preferences file not found: ${ITERM2_PREFERENCES_PATH} (optional feature - continuing)"
   else
     log "iTerm2 not configured - skipping iTerm2 preferences setup"
   fi
@@ -366,17 +441,20 @@ main() {
 
   configure_terminal_profiles
 
-  # Simple completion message
+  # Since terminal profiles are optional, always report success
+  # Any failures in optional operations are handled as warnings, not errors
   local error_count=${#COLLECTED_ERRORS[@]}
 
   if [[ ${error_count} -eq 0 ]]; then
     show_log "✅ Terminal profile configuration completed successfully"
     show_log "ℹ️  Restart Terminal and iTerm2 to see new profiles"
-    return 0
   else
-    show_log "❌ Terminal profile configuration completed with ${error_count} errors"
-    return 1
+    show_log "✅ Terminal profile configuration completed (${error_count} non-critical issues)"
+    show_log "ℹ️  Check logs for details on optional profile import issues"
+    show_log "ℹ️  Restart Terminal and iTerm2 to see any successfully imported profiles"
   fi
+
+  return 0 # Always return success since this is an optional module
 }
 
 # Execute main function