diff --git a/api/get_conversation_detail.php b/api/get_conversation_detail.php
index e0e1c80..619cf16 100644
--- a/api/get_conversation_detail.php
+++ b/api/get_conversation_detail.php
@@ -135,7 +135,9 @@ try {
             'in_service' => !empty($user['in_service']) ? true : false,
             'in_service_by' => isset($user['in_service_by']) ? intval($user['in_service_by']) : null,
             'in_service_at' => $user['in_service_at'] ?? null,
-            'in_service_by_name' => $inServiceByName
+            'in_service_by_name' => $inServiceByName,
+            'advisor_requested' => !empty($user['advisor_requested']) ? true : false,
+            'on_hold' => !empty($user['on_hold']) ? true : false
         ],
         'conversations' => $conversations,
         'total_conversations' => count($conversations)
diff --git a/api/get_conversation_list.php b/api/get_conversation_list.php
index 17a04f8..1a6a0c2 100644
--- a/api/get_conversation_list.php
+++ b/api/get_conversation_list.php
@@ -31,6 +31,7 @@ try {
             c.message_type as last_message_type,
             c.created_at as last_message_time,
             c.status as last_message_status,
+            u.advisor_requested as advisor_requested,
             COUNT(*) as total_conversations,
             SUM(CASE WHEN c.direction = 'incoming' AND c.status = 'received' THEN 1 ELSE 0 END) as unread_count
          FROM users u
@@ -40,7 +41,7 @@ try {
              FROM conversations 
              GROUP BY user_id
          )
-         GROUP BY u.id, u.phone_number, u.name, c.content, c.direction, c.message_type, c.created_at, c.status
+         GROUP BY u.id, u.phone_number, u.name, c.content, c.direction, c.message_type, c.created_at, c.status, u.advisor_requested
          ORDER BY c.created_at DESC
          LIMIT 50"
     );
@@ -61,6 +62,7 @@ try {
             'last_message_type' => $conv['last_message_type'] ?? 'text',
             'last_message_time' => $conv['last_message_time'],
             'last_message_status' => $conv['last_message_status'] ?? 'sent',
+            'advisor_requested' => !empty($conv['advisor_requested']) ? true : false,
             'total_conversations' => intval($conv['total_conversations']),
             'unread_count' => intval($conv['unread_count']),
             'time_ago' => timeAgo($conv['last_message_time'])
diff --git a/assets/css/styles.css b/assets/css/styles.css
index 185d7fd..b148420 100644
--- a/assets/css/styles.css
+++ b/assets/css/styles.css
@@ -1164,6 +1164,15 @@ body {
     box-shadow: 0 6px 18px rgba(11, 122, 87, 0.25);
 }
 
+/* Conversation requiring advisor attention */
+.conversation-item.attention {
+    border-left: 4px solid #dc3545;
+    background: rgba(220, 53, 69, 0.03);
+}
+.conversation-item.attention .conversation-avatar {
+    box-shadow: 0 6px 18px rgba(220, 53, 69, 0.12);
+}
+
 /* Notification bell indicator when there are unseen notifications */
 #notification-bell.has-notifications {
     position: relative;
diff --git a/assets/js/app_simple.js b/assets/js/app_simple.js
index 72713bd..a0e8149 100644
--- a/assets/js/app_simple.js
+++ b/assets/js/app_simple.js
@@ -515,6 +515,10 @@ class SimpleWhatsAppManager {
             // Add class to highlight unread conversation (darker green)
             const unreadClass = (conv.unread_count && conv.unread_count > 0) ? ' unread' : '';
 
+            // Attention badge for advisor requests
+            const attentionBadge = conv.advisor_requested ? `<div class="conversation-attention" title="Requiere atención"><i class="fas fa-exclamation"></i></div>` : '';
+            const attentionClass = conv.advisor_requested ? ' attention' : '';
+
             // Status icon
             const statusIcon = conv.last_direction === 'outgoing' 
                 ? '<i class="fas fa-check-double conversation-status-icon outgoing"></i>'
@@ -528,7 +532,7 @@ class SimpleWhatsAppManager {
                 : '';
 
             html += `
-                <div class="conversation-item${unreadClass}" onclick="openChatWindow(${conv.user_id})">
+                <div class="conversation-item${unreadClass}${attentionClass}" onclick="openChatWindow(${conv.user_id})">
                     <div class="conversation-avatar ${isOnline ? 'online' : ''}">
                         ${userInitial}
                     </div>
@@ -549,6 +553,7 @@ class SimpleWhatsAppManager {
                     </div>
                     <div class="conversation-meta">
                         ${unreadBadge}
+                        ${attentionBadge}
                         <div class="conversation-actions">
                             <button class="btn btn-sm" onclick="event.stopPropagation(); openChatWindow(${conv.user_id})" title="Abrir chat">
                                 <i class="fas fa-comments"></i>
@@ -635,7 +640,7 @@ class SimpleWhatsAppManager {
             const unreadClass = (conv.unread_count && conv.unread_count > 0) ? ' unread' : '';
 
             html += `
-                <div class="conversation-item${unreadClass}" onclick="openChatWindow(${conv.user_id})">
+                <div class="conversation-item${unreadClass}${attentionClass}" onclick="openChatWindow(${conv.user_id})">
                     <div class="conversation-avatar ${isOnline ? 'online' : ''}">
                         ${userInitial}
                     </div>
@@ -656,6 +661,7 @@ class SimpleWhatsAppManager {
                     </div>
                     <div class="conversation-meta">
                         ${unreadBadge}
+                        ${attentionBadge}
                         <div class="conversation-actions">
                             <button class="btn btn-sm" onclick="event.stopPropagation(); openChatWindow(${conv.user_id})" title="Abrir chat">
                                 <i class="fas fa-comments"></i>
diff --git a/chat_window.php b/chat_window.php
index cd4bcff..864bd82 100644
--- a/chat_window.php
+++ b/chat_window.php
@@ -200,6 +200,35 @@ if (empty($user_id)) {
             font-size: 0.65rem;
             opacity: 0.85;
         }
+
+        /* Mensajes que requieren atención (asesor) */
+        .message-alert {
+            background: #fff7f7 !important;
+            border-left: 4px solid #dc3545 !important;
+            color: #6b0000;
+        }
+
+        .header-advisor-badge {
+            display: inline-block;
+            background: #dc3545;
+            color: white;
+            padding: 2px 6px;
+            border-radius: 12px;
+            font-size: 0.75rem;
+            margin-left: 8px;
+        }
+
+        .conversation-attention {
+            display: flex;
+            align-items: center;
+            justify-content: center;
+            width: 28px;
+            height: 28px;
+            border-radius: 50%;
+            background: #dc3545;
+            color: white;
+            font-size: 0.9rem;
+        }
         
         /* Estilos para multimedia */
         .attach-btn {
@@ -358,11 +387,11 @@ if (empty($user_id)) {
                         <i class="fas fa-user"></i>
                     </div>
                     <div>
-                        <h5 class="mb-0" id="userName">Cargando...</h5>
+                        <h5 class="mb-0" id="userName">Cargando... <span id="advisorBadge" style="display:none;" class="header-advisor-badge">¡Atención!</span></h5>
                         <small class="status-indicator" id="userStatus">
                             <i class="fas fa-circle text-success"></i> En línea
                         </small>
-                    </div>
+                    </div> 
                 </div>
                 <div class="d-flex align-items-center">
                     <button id="attendBtn" class="btn btn-outline-light btn-sm me-2" onclick="toggleAttend()" title="Atender/Finalizar">
@@ -696,6 +725,16 @@ if (empty($user_id)) {
                     document.getElementById('userAvatar').innerHTML = 
                         `<span>${(currentUser.name || 'U').charAt(0).toUpperCase()}</span>`;
                     
+                    // Mostrar badge de atención si existe
+                    try {
+                        const advisorBadge = document.getElementById('advisorBadge');
+                        if (advisorBadge) {
+                            advisorBadge.style.display = currentUser.advisor_requested ? 'inline-block' : 'none';
+                        }
+                    } catch (e) {
+                        // ignore
+                    }
+
                     // Estado de atención
                     renderAttendControls();
                     
@@ -735,7 +774,7 @@ if (empty($user_id)) {
             let html = '';
             conversations.forEach(msg => {
                 const isOutgoing = msg.direction === 'outgoing';
-                const messageClass = isOutgoing ? 'message-outgoing' : 'message-incoming';
+                let messageClass = isOutgoing ? 'message-outgoing' : 'message-incoming';
                 
                 // Debug: ver todos los datos del mensaje (prioriza media_url_external y valida URLs)
                 const has_media_external = isValidMediaUrl(msg.media_url_external);
@@ -923,7 +962,26 @@ if (empty($user_id)) {
                     }
                 } else {
                     // Mensaje de texto normal
-                    contentHtml = escapeHtml(msg.content) || '<em>Sin contenido</em>';
+                    // Detectar mensajes 'system' embebidos en content (JSON)
+                    let alertInfo = null;
+                    try {
+                        const parsed = JSON.parse(msg.content || '');
+                        if (parsed && parsed.system) {
+                            alertInfo = parsed;
+                        }
+                    } catch (e) {
+                        // No es JSON, seguir
+                    }
+
+                    if (alertInfo) {
+                        contentHtml = `<div class="fw-bold">${escapeHtml(alertInfo.text || '[Atención]')}</div>`;
+                        // Añadir clase especial a la burbuja
+                        // marca el mensaje como requiring attention mediante messageClass
+                        // we'll append an additional class later
+                        messageClass += ' message-alert';
+                    } else {
+                        contentHtml = escapeHtml(msg.content) || '<em>Sin contenido</em>';
+                    }
                 }
                 
                 const messageTime = escapeHtml(msg.time || '');
diff --git a/conversations.php b/conversations.php
index e83c7ef..70aadd9 100644
--- a/conversations.php
+++ b/conversations.php
@@ -733,17 +733,19 @@
                     const avatar = conv.avatar_url ? `<img src="${conv.avatar_url}" alt="avatar" class="conversation-avatar-img">` : `<div class="conversation-avatar">${this.getInitials(conv.name)}</div>`;
 
                     const unreadBadge = conv.unread_count && conv.unread_count > 0 ? `<span class="badge bg-danger unread-badge">${conv.unread_count}</span>` : '';
+                    const attentionBadge = conv.advisor_requested ? `<span class="badge bg-danger ms-1">¡Atención!</span>` : '';
 
                     // different color if has unread and not active
                     const unreadClass = (conv.unread_count && conv.unread_count > 0 && !isActive) ? 'unread' : '';
+                    const attentionClass = conv.advisor_requested ? ' attention' : '';
 
                     return `
-                        <div class="conversation-item ${isActive} ${unreadClass}" data-user-id="${conv.user_id}" onclick="chat.openConversation(${conv.user_id}, '${conv.name}', '${conv.phone_number}')">
+                        <div class="conversation-item ${isActive} ${unreadClass}${attentionClass}" data-user-id="${conv.user_id}" onclick="chat.openConversation(${conv.user_id}, '${conv.name}', '${conv.phone_number}')">
                             <div class="conversation-avatar-wrapper">
                                 ${avatar}
                             </div>
                             <div class="conversation-info">
-                                <div class="conversation-name">${conv.name} ${unreadBadge}</div>
+                                <div class="conversation-name">${conv.name} ${unreadBadge} ${attentionBadge}</div>
                                 <div class="conversation-preview">
                                     ${conv.direction === 'outgoing' ? '✓ ' : ''}${preview}
                                 </div>
diff --git a/services/BotService.php b/services/BotService.php
index 551cc69..7bed435 100644
--- a/services/BotService.php
+++ b/services/BotService.php
@@ -69,7 +69,30 @@ class BotService {
                 } catch (Exception $e) {
                     // ignore send errors
                 }
-                error_log("[BotService] processMessage - sent 'enviados' ack to user {$user['id']}");
+
+                // Marcar para atención humana y crear un system message para que el asesor lo vea
+                try {
+                    $this->db->update('users', ['advisor_requested' => 1], 'phone_number = :phone', ['phone' => $phoneNumber]);
+
+                    $sys = [
+                        'system' => 'attention',
+                        'type' => 'user_sent_documents',
+                        'text' => 'El usuario indicó que ha enviado documentos o información; requiere atención.'
+                    ];
+
+                    $this->db->insert('conversations', [
+                        'user_id' => $user['id'],
+                        'direction' => 'incoming',
+                        'message_type' => 'text',
+                        'content' => json_encode($sys),
+                        'status' => 'received',
+                        'created_at' => date('Y-m-d H:i:s')
+                    ]);
+                } catch (Exception $e) {
+                    error_log('[BotService] failed to mark advisor_requested on envio: ' . $e->getMessage());
+                }
+
+                error_log("[BotService] processMessage - sent 'enviados' ack to user {$user['id']} and marked advisor_requested");
                 return;
             }
         } catch (Throwable $t) {
@@ -508,6 +531,22 @@ class BotService {
             // No ponemos on_hold para evitar bloqueo automático; usamos advisor_requested
             $this->db->update('users', ['advisor_requested' => 1, 'bot_paused_until' => $pausedUntil], 'phone_number = :phone', ['phone' => $phoneNumber]);
             $this->whatsappService->sendTextMessage($phoneNumber, "🔔 Te hemos transferido con un asesor, te responderemos en breve.");
+
+            // Crear un mensaje 'system' en la conversación para que el equipo lo detecte fácilmente
+            try {
+                $user = $this->db->fetch('SELECT id FROM users WHERE phone_number = :phone', ['phone' => $phoneNumber]);
+                $this->db->insert('conversations', [
+                    'user_id' => $user['id'] ?? null,
+                    'direction' => 'incoming',
+                    'message_type' => 'text',
+                    'content' => json_encode(['system' => 'advisor_request', 'text' => 'Usuario solicitó asesor']),
+                    'status' => 'received',
+                    'created_at' => date('Y-m-d H:i:s')
+                ]);
+            } catch (Exception $e) {
+                error_log('[BotService] requestAdvisor - failed to insert system message: ' . $e->getMessage());
+            }
+
             if (function_exists('writeLog')) writeLog('INFO', "Advisor solicited for $phoneNumber until $pausedUntil");
         } catch (Exception $e) {
             error_log('requestAdvisor failed: ' . $e->getMessage());