diff --git a/modules/website/wordpress/wordpress-cron-manager.sh b/modules/website/wordpress/wordpress-cron-manager.sh
index 9d27477..4ef1c4d 100755
--- a/modules/website/wordpress/wordpress-cron-manager.sh
+++ b/modules/website/wordpress/wordpress-cron-manager.sh
@@ -1018,6 +1018,118 @@ report_save() {
     fi
 }
 
+# ADVANCED FEATURE: Automatic Rollback Support (OPT-19)
+# Provides safety net for large-scale operations with ability to revert changes
+# Creates checkpoint backups and enables reverting to known-good state
+declare -g ROLLBACK_ENABLED=false
+declare -g ROLLBACK_DIR="/tmp/wp-cron-rollback-$$"
+declare -gA ROLLBACK_BACKUPS  # Maps wp-config.php path to backup path
+
+# Initialize rollback system
+rollback_init() {
+    if [ "$DRY_RUN" = "true" ]; then
+        return 0  # Skip rollback in dry-run mode
+    fi
+
+    ROLLBACK_ENABLED=true
+    mkdir -p "$ROLLBACK_DIR" 2>/dev/null
+
+    if [ ! -d "$ROLLBACK_DIR" ]; then
+        print_warning "Could not create rollback directory: $ROLLBACK_DIR"
+        ROLLBACK_ENABLED=false
+        return 1
+    fi
+
+    return 0
+}
+
+# Create checkpoint backup before modification
+rollback_create_checkpoint() {
+    local wp_config="$1"
+    local backup_path="$ROLLBACK_DIR/$(basename "$wp_config").bak"
+
+    if [ ! "$ROLLBACK_ENABLED" = "true" ]; then
+        return 0
+    fi
+
+    if ! cp "$wp_config" "$backup_path" 2>/dev/null; then
+        print_error "Failed to create rollback checkpoint: $wp_config"
+        return 1
+    fi
+
+    # Store mapping for later rollback
+    ROLLBACK_BACKUPS["$wp_config"]="$backup_path"
+    return 0
+}
+
+# Restore file from rollback checkpoint
+rollback_restore_file() {
+    local wp_config="$1"
+    local backup_path="${ROLLBACK_BACKUPS[$wp_config]}"
+
+    if [ ! -f "$backup_path" ]; then
+        print_error "No rollback checkpoint found for: $wp_config"
+        return 1
+    fi
+
+    if ! cp "$backup_path" "$wp_config" 2>/dev/null; then
+        print_error "Failed to restore from rollback checkpoint: $wp_config"
+        return 1
+    fi
+
+    print_success "Restored from checkpoint: $wp_config"
+    return 0
+}
+
+# Rollback all changes to checkpoint
+rollback_all() {
+    if [ ! "$ROLLBACK_ENABLED" = "true" ]; then
+        print_error "Rollback not enabled"
+        return 1
+    fi
+
+    if [ ${#ROLLBACK_BACKUPS[@]} -eq 0 ]; then
+        print_info "No checkpoints to rollback"
+        return 0
+    fi
+
+    print_warning "Rolling back ${#ROLLBACK_BACKUPS[@]} modified files..."
+
+    local failed=0
+    for wp_config in "${!ROLLBACK_BACKUPS[@]}"; do
+        if ! rollback_restore_file "$wp_config"; then
+            failed=$((failed + 1))
+        fi
+    done
+
+    if [ $failed -eq 0 ]; then
+        print_success "All files restored successfully"
+        return 0
+    else
+        print_error "Failed to restore $failed files"
+        return 1
+    fi
+}
+
+# Clean up rollback directory
+rollback_cleanup() {
+    if [ -d "$ROLLBACK_DIR" ]; then
+        rm -rf "$ROLLBACK_DIR" 2>/dev/null
+    fi
+}
+
+# Rollback trap handler (called on EXIT/INT/TERM)
+rollback_on_interrupt() {
+    if [ "$ROLLBACK_ENABLED" = "true" ]; then
+        echo ""
+        print_warning "Operation interrupted"
+        if confirm "Rollback all changes?"; then
+            rollback_all
+        fi
+    fi
+    rollback_cleanup
+}
+
 # OPTIMIZATION: Build cron command consistently
 # Centralizes cron command format (appears 4 times throughout script)
 # Returns: cron command string for wp-cron.php execution