diff --git a/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/class-hvac-community-events.php b/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/class-hvac-community-events.php
index 560e20dd..68577393 100644
--- a/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/class-hvac-community-events.php
+++ b/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/class-hvac-community-events.php
@@ -64,7 +64,8 @@ class HVAC_Community_Events {
 	        'certificates/class-certificate-settings.php',   // Certificate settings
 	        'certificates/class-certificate-template.php',   // Certificate template
 	        'certificates/class-certificate-security.php',   // Certificate security
-	        'certificates/class-certificate-ajax-handler.php' // Certificate AJAX handling
+	        'certificates/class-certificate-ajax-handler.php', // Certificate AJAX handling
+	        'community/class-email-debug.php'    // Email debugging tools
 	    ];
 	    // Make sure Login_Handler is loaded first for shortcode registration
 	    $login_handler_path = HVAC_CE_PLUGIN_DIR . 'includes/community/class-login-handler.php';
diff --git a/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-attendees-data.php b/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-attendees-data.php
index 8f1e7ffd..a37d2fe7 100644
--- a/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-attendees-data.php
+++ b/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-attendees-data.php
@@ -253,7 +253,14 @@ class HVAC_Email_Attendees_Data {
      * @return array Result with status and message.
      */
     public function send_email( $recipients, $subject, $message, $cc = '' ) {
+        // Start debug log
+        $debug_log = "=== Email Sending Debug ===\n";
+        
         if ( empty( $recipients ) || empty( $subject ) || empty( $message ) ) {
+            $debug_log .= "Error: Missing required fields\n";
+            if (class_exists('HVAC_Logger')) {
+                HVAC_Logger::error('Email sending failed: Missing required fields', 'Email System');
+            }
             return array(
                 'success' => false,
                 'message' => 'Missing required fields (recipients, subject, or message).',
@@ -261,6 +268,10 @@ class HVAC_Email_Attendees_Data {
         }
 
         if ( ! $this->is_valid_event() || ! $this->user_can_email_attendees() ) {
+            $debug_log .= "Error: Permission denied\n";
+            if (class_exists('HVAC_Logger')) {
+                HVAC_Logger::error('Email sending failed: Permission denied', 'Email System');
+            }
             return array(
                 'success' => false,
                 'message' => 'You do not have permission to email attendees for this event.',
@@ -270,6 +281,7 @@ class HVAC_Email_Attendees_Data {
         $headers = array('Content-Type: text/html; charset=UTF-8');
         $event_details = $this->get_event_details();
         $event_title = $event_details['title'];
+        $debug_log .= "Event: {$event_title} (ID: {$this->event_id})\n";
         
         // Add CC if provided
         if ( ! empty( $cc ) ) {
@@ -278,6 +290,7 @@ class HVAC_Email_Attendees_Data {
                 $cc_email = trim( $cc_email );
                 if ( is_email( $cc_email ) ) {
                     $headers[] = 'Cc: ' . $cc_email;
+                    $debug_log .= "Added CC: {$cc_email}\n";
                 }
             }
         }
@@ -287,48 +300,123 @@ class HVAC_Email_Attendees_Data {
         $from_name = $current_user->display_name;
         $from_email = $current_user->user_email;
         $headers[] = 'From: ' . $from_name . ' <' . $from_email . '>';
+        $debug_log .= "From: {$from_name} <{$from_email}>\n";
 
         // Process recipients
         $all_attendees = $this->get_attendees();
+        $debug_log .= "Total attendees found: " . count($all_attendees) . "\n";
+        
         $attendee_emails = array();
         $sent_count = 0;
         $error_count = 0;
 
+        $debug_log .= "Recipients provided: " . count($recipients) . "\n";
+        
         // Handle numeric IDs or email addresses
         foreach ( $recipients as $recipient ) {
+            $debug_log .= "Processing recipient: {$recipient}\n";
+            
             if ( is_numeric( $recipient ) ) {
+                $debug_log .= "Recipient is numeric ID\n";
                 // Find attendee by ID
                 foreach ( $all_attendees as $attendee ) {
                     if ( $attendee['attendee_id'] == $recipient ) {
                         $attendee_emails[$attendee['email']] = $attendee['name'];
+                        $debug_log .= "Matched with attendee: {$attendee['name']} <{$attendee['email']}>\n";
                         break;
                     }
                 }
             } elseif ( is_email( $recipient ) ) {
+                $debug_log .= "Recipient is email address\n";
                 // Add directly if it's an email
                 $attendee_name = '';
                 foreach ( $all_attendees as $attendee ) {
                     if ( $attendee['email'] === $recipient ) {
                         $attendee_name = $attendee['name'];
+                        $debug_log .= "Matched with attendee name: {$attendee_name}\n";
                         break;
                     }
                 }
                 $attendee_emails[$recipient] = $attendee_name;
+            } else {
+                $debug_log .= "Invalid recipient format\n";
+            }
+        }
+
+        $debug_log .= "Recipients to email: " . count($attendee_emails) . "\n";
+        
+        if (empty($attendee_emails)) {
+            $debug_log .= "No valid recipients found! Using fallback to direct send.\n";
+            
+            // Fallback - directly use the first selected email
+            foreach ($recipients as $recipient) {
+                if (is_email($recipient)) {
+                    $attendee_emails[$recipient] = '';
+                    $debug_log .= "Added direct recipient: {$recipient}\n";
+                    break;
+                }
             }
         }
 
         // Subject with event title
         $email_subject = sprintf( '[%s] %s', $event_title, $subject );
+        $debug_log .= "Email subject: {$email_subject}\n";
 
         // Send to each recipient individually for personalization
         foreach ( $attendee_emails as $email => $name ) {
+            $debug_log .= "Sending to: {$email}\n";
+            
             // Personalize message with attendee name if available
             $personalized_message = $message;
             if ( ! empty( $name ) ) {
                 $personalized_message = "Hello " . $name . ",\n\n" . $message;
+                $debug_log .= "Personalized with name: {$name}\n";
             }
 
-            $mail_sent = wp_mail( $email, $email_subject, wpautop( $personalized_message ), $headers );
+            // Log complete mail params for debugging
+            $debug_log .= "Mail parameters:\n";
+            $debug_log .= "To: {$email}\n";
+            $debug_log .= "Subject: {$email_subject}\n";
+            $debug_log .= "Headers: " . print_r($headers, true) . "\n";
+            
+            // Add error logger for wp_mail
+            add_action('wp_mail_failed', function($wp_error) use (&$debug_log) {
+                $debug_log .= "Mail error: " . $wp_error->get_error_message() . "\n";
+                if (class_exists('HVAC_Logger')) {
+                    HVAC_Logger::error('WordPress Mail Error: ' . $wp_error->get_error_message(), 'Email System');
+                }
+            });
+            
+            // Use server email settings temporarily to avoid host-specific issues
+            $debug_log .= "Using PHP mail() settings\n";
+            add_filter('pre_wp_mail', function($null, $atts) use ($email, $email_subject, $personalized_message, $headers, &$debug_log) {
+                // Try sending with PHP mail directly
+                $to = $email;
+                $subject = $email_subject;
+                $message = wpautop($personalized_message);
+                $headers_string = implode("\r\n", $headers);
+                
+                $debug_log .= "Using PHP mail() function directly\n";
+                
+                $mail_sent = mail($to, $subject, $message, $headers_string);
+                
+                $debug_log .= "PHP mail() result: " . ($mail_sent ? 'Success' : 'Failed') . "\n";
+                
+                // Return true to indicate we've handled the email
+                if ($mail_sent) {
+                    return true;
+                }
+                
+                // Return null to let wp_mail proceed with its normal process
+                return $null;
+            }, 10, 2);
+            
+            $mail_sent = wp_mail($email, $email_subject, wpautop($personalized_message), $headers);
+            
+            // Remove the filter after sending
+            remove_filter('pre_wp_mail', function(){}, 10);
+            
+            $debug_log .= "wp_mail result: " . ($mail_sent ? 'Success' : 'Failed') . "\n";
             
             if ( $mail_sent ) {
                 $sent_count++;
@@ -337,6 +425,11 @@ class HVAC_Email_Attendees_Data {
             }
         }
 
+        // Log the complete debug information
+        if (class_exists('HVAC_Logger')) {
+            HVAC_Logger::info($debug_log, 'Email System');
+        }
+        
         // Return results
         if ( $error_count > 0 ) {
             return array(
diff --git a/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-debug.php b/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-debug.php
new file mode 100644
index 00000000..ef6d7afa
--- /dev/null
+++ b/wordpress-dev/wordpress/wp-content/plugins/hvac-community-events/includes/community/class-email-debug.php
@@ -0,0 +1,244 @@
+<?php
+/**
+ * HVAC Community Events - Email Debugging Class
+ *
+ * Provides debugging tools for email functionality.
+ *
+ * @package HVAC_Community_Events
+ * @subpackage Community
+ */
+
+// Exit if accessed directly
+if (!defined('ABSPATH')) {
+    exit;
+}
+
+/**
+ * Class HVAC_Email_Debug
+ *
+ * Debugging tools for email functionality.
+ */
+class HVAC_Email_Debug {
+    /**
+     * Initialize debugging hooks
+     */
+    public static function init() {
+        // Add debugging AJAX action
+        add_action('wp_ajax_hvac_debug_email_attendees', [self::class, 'debug_email_attendees']);
+        
+        // Add debugging button to admin footer on email attendees page
+        add_action('wp_footer', [self::class, 'add_debug_button']);
+        
+        // Debug wp_mail
+        add_action('wp_mail_failed', [self::class, 'log_mail_error']);
+    }
+    
+    /**
+     * Add debug button to the email attendees page
+     */
+    public static function add_debug_button() {
+        // Only add on email attendees page
+        if (!is_page('email-attendees')) {
+            return;
+        }
+        
+        // Get event ID from URL
+        $event_id = isset($_GET['event_id']) ? intval($_GET['event_id']) : 0;
+        if ($event_id <= 0) {
+            return;
+        }
+        
+        // Add debug button
+        ?>
+        <div style="position: fixed; bottom: 20px; right: 20px; z-index: 9999;">
+            <button id="hvac-debug-email" class="button" data-event-id="<?php echo esc_attr($event_id); ?>">Debug Email System</button>
+        </div>
+        
+        <div id="hvac-debug-output" style="display:none; position: fixed; top: 50px; left: 50px; right: 50px; bottom: 50px; background: #fff; border: 2px solid #333; padding: 20px; overflow: auto; z-index: 10000;">
+            <h2>Email System Debug Output</h2>
+            <pre id="hvac-debug-content" style="white-space: pre-wrap; font-family: monospace;"></pre>
+            <button id="hvac-debug-close" class="button" style="position: absolute; top: 10px; right: 10px;">Close</button>
+        </div>
+        
+        <script>
+            jQuery(document).ready(function($) {
+                $('#hvac-debug-email').on('click', function() {
+                    var eventId = $(this).data('event-id');
+                    $('#hvac-debug-content').html('Loading debug information...');
+                    $('#hvac-debug-output').show();
+                    
+                    $.ajax({
+                        url: ajaxurl,
+                        type: 'POST',
+                        data: {
+                            action: 'hvac_debug_email_attendees',
+                            event_id: eventId,
+                            nonce: '<?php echo wp_create_nonce('hvac_debug_email'); ?>'
+                        },
+                        success: function(response) {
+                            $('#hvac-debug-content').html(response.data || 'No debug data returned.');
+                        },
+                        error: function() {
+                            $('#hvac-debug-content').html('Error fetching debug information.');
+                        }
+                    });
+                });
+                
+                $('#hvac-debug-close').on('click', function() {
+                    $('#hvac-debug-output').hide();
+                });
+            });
+        </script>
+        <?php
+    }
+    
+    /**
+     * Debug email attendees functionality
+     */
+    public static function debug_email_attendees() {
+        // Verify nonce
+        if (!isset($_POST['nonce']) || !wp_verify_nonce($_POST['nonce'], 'hvac_debug_email')) {
+            wp_send_json_error('Invalid nonce');
+            return;
+        }
+        
+        // Get event ID
+        $event_id = isset($_POST['event_id']) ? intval($_POST['event_id']) : 0;
+        if ($event_id <= 0) {
+            wp_send_json_error('Invalid event ID');
+            return;
+        }
+        
+        // Create debug output
+        $output = "=== EMAIL SYSTEM DEBUG ===\n\n";
+        
+        // Check if user is logged in
+        $output .= "User login status: " . (is_user_logged_in() ? 'Logged in' : 'Not logged in') . "\n";
+        if (is_user_logged_in()) {
+            $current_user = wp_get_current_user();
+            $output .= "Current user: " . $current_user->display_name . " (" . $current_user->user_email . ")\n";
+            $output .= "User roles: " . implode(', ', $current_user->roles) . "\n";
+        }
+        
+        // Check event
+        $output .= "\n=== EVENT INFORMATION ===\n";
+        $event = get_post($event_id);
+        if (!$event) {
+            $output .= "Event ID {$event_id} not found.\n";
+        } else {
+            $output .= "Event ID: {$event_id}\n";
+            $output .= "Event title: " . get_the_title($event) . "\n";
+            $output .= "Event status: " . get_post_status($event) . "\n";
+            $output .= "Event author: " . $event->post_author . "\n";
+            
+            // Check if user can edit event
+            $output .= "Current user can edit event: " . (get_current_user_id() === (int)$event->post_author || current_user_can('edit_posts') ? 'Yes' : 'No') . "\n";
+        }
+        
+        // Get attendees
+        $output .= "\n=== ATTENDEES DATA ===\n";
+        require_once HVAC_CE_PLUGIN_DIR . 'includes/community/class-email-attendees-data.php';
+        $email_data = new HVAC_Email_Attendees_Data($event_id);
+        
+        // Check if event is valid
+        $output .= "Event is valid: " . ($email_data->is_valid_event() ? 'Yes' : 'No') . "\n";
+        $output .= "User can email attendees: " . ($email_data->user_can_email_attendees() ? 'Yes' : 'No') . "\n";
+        
+        // Get attendees
+        $attendees = $email_data->get_attendees();
+        $output .= "Number of attendees found: " . count($attendees) . "\n\n";
+        
+        if (!empty($attendees)) {
+            $output .= "Attendee details:\n";
+            foreach ($attendees as $index => $attendee) {
+                $output .= "--- Attendee " . ($index + 1) . " ---\n";
+                $output .= "Name: " . (!empty($attendee['name']) ? $attendee['name'] : 'No name') . "\n";
+                $output .= "Email: " . (!empty($attendee['email']) ? $attendee['email'] : 'No email') . "\n";
+                $output .= "Ticket: " . (!empty($attendee['ticket_name']) ? $attendee['ticket_name'] : 'No ticket name') . "\n";
+                $output .= "Attendee ID: " . (!empty($attendee['attendee_id']) ? $attendee['attendee_id'] : 'No ID') . "\n";
+                $output .= "Order ID: " . (!empty($attendee['order_id']) ? $attendee['order_id'] : 'No order ID') . "\n\n";
+            }
+        }
+        
+        // Test direct attendee query
+        $output .= "\n=== DIRECT ATTENDEE QUERY ===\n";
+        $query_args = [
+            'post_type' => 'tribe_tpp_attendees',
+            'posts_per_page' => -1,
+            'meta_query' => [
+                [
+                    'key' => '_tribe_tpp_event',
+                    'value' => $event_id,
+                    'compare' => '=',
+                ],
+            ],
+        ];
+        
+        $attendees_query = new WP_Query($query_args);
+        $output .= "Direct query found posts: " . $attendees_query->found_posts . "\n";
+        
+        if ($attendees_query->have_posts()) {
+            while ($attendees_query->have_posts()) {
+                $attendees_query->the_post();
+                $attendee_id = get_the_ID();
+                
+                $output .= "- Post ID: {$attendee_id}, Title: " . get_the_title() . "\n";
+                
+                // Get metadata
+                $email = get_post_meta($attendee_id, '_tribe_tickets_email', true);
+                if (empty($email)) {
+                    $email = get_post_meta($attendee_id, '_tribe_tpp_email', true);
+                }
+                
+                $output .= "  Email: " . ($email ?: 'None') . "\n";
+                
+                // Check other important meta
+                $ticket_id = get_post_meta($attendee_id, '_tribe_tpp_product', true);
+                $output .= "  Ticket ID: " . ($ticket_id ?: 'None') . "\n";
+                
+                if ($ticket_id) {
+                    $output .= "  Ticket Title: " . get_the_title($ticket_id) . "\n";
+                }
+                
+                $output .= "  Order ID: " . get_post_meta($attendee_id, '_tribe_tpp_order', true) . "\n";
+                $output .= "  Check-in: " . get_post_meta($attendee_id, '_tribe_tpp_checkin', true) . "\n";
+                $output .= "\n";
+            }
+            wp_reset_postdata();
+        }
+        
+        // Test email functionality
+        $output .= "\n=== EMAIL FUNCTIONALITY ===\n";
+        $output .= "WordPress mail function available: " . (function_exists('wp_mail') ? 'Yes' : 'No') . "\n";
+        
+        // Get mail settings
+        $output .= "Mail configuration:\n";
+        $admin_email = get_option('admin_email');
+        $output .= "Admin email: {$admin_email}\n";
+        
+        $output .= "Mail test: ";
+        // Don't actually send mail in debug, just check configuration
+        $output .= "Not sending test email to avoid mail server load\n";
+        
+        $output .= "\nNote: If you need to send a test email, you can use the form on the page with a minimal set of recipients.\n";
+        
+        // Return debug output
+        wp_send_json_success($output);
+    }
+    
+    /**
+     * Log mail errors
+     */
+    public static function log_mail_error($wp_error) {
+        $error_message = $wp_error->get_error_message();
+        error_log('WordPress Mail Error: ' . $error_message);
+        
+        // Also log to our custom file if logging is enabled
+        if (class_exists('HVAC_Logger')) {
+            HVAC_Logger::error('WordPress Mail Error: ' . $error_message, 'Email System');
+        }
+    }
+}
+
+// Initialize the debugging class
+HVAC_Email_Debug::init();
\ No newline at end of file