diff --git a/app/components/debug/HistorySection.vue b/app/components/debug/HistorySection.vue
index 2f52d4a..95f0c49 100644
--- a/app/components/debug/HistorySection.vue
+++ b/app/components/debug/HistorySection.vue
@@ -4,43 +4,105 @@
     <div class="space-y-4">
       <h3 class="text-lg font-medium text-[var(--wa-text)]">Solicitar Historial de Mensajes</h3>
       <p class="text-sm text-[var(--wa-text-muted)]">
-        Solicita mensajes adicionales del historial. Los resultados llegaran via el evento messaging-history.set.
+        Solicita mensajes adicionales del historial de WhatsApp. Los mensajes se guardaran en la base de datos.
       </p>
-      <div class="grid grid-cols-2 gap-4">
+
+      <!-- Chat Selector -->
+      <div class="space-y-2">
+        <label class="text-sm text-[var(--wa-text-muted)]">Seleccionar Chat</label>
+        <USelectMenu
+          v-model="selectedChat"
+          :items="chatOptions"
+          placeholder="Seleccionar chat..."
+          searchable
+          :loading="loadingChats"
+          class="w-full"
+        />
+      </div>
+
+      <!-- Selected Chat Info -->
+      <div v-if="selectedChat && oldestMessage" class="p-3 rounded bg-[var(--wa-bg-hover)] space-y-1">
+        <p class="text-sm text-[var(--wa-text)]">
+          <span class="text-[var(--wa-text-muted)]">Chat:</span> {{ selectedChat.label }}
+        </p>
+        <p class="text-sm text-[var(--wa-text)]">
+          <span class="text-[var(--wa-text-muted)]">Mensaje mas antiguo:</span>
+          {{ formatDate(oldestMessage.timestamp) }}
+        </p>
+      </div>
+
+      <div v-else-if="selectedChat && !loadingOldest" class="p-3 rounded bg-yellow-900/20 text-yellow-400 text-sm">
+        Este chat no tiene mensajes guardados en la base de datos.
+      </div>
+
+      <!-- Count Input -->
+      <div class="space-y-2">
+        <label class="text-sm text-[var(--wa-text-muted)]">Cantidad de mensajes a solicitar</label>
         <UInput
           v-model.number="count"
           type="number"
           placeholder="Cantidad de mensajes"
           :min="1"
           :max="1000"
-        />
-        <UInput
-          v-model.number="oldestMsgTimestamp"
-          type="number"
-          placeholder="Timestamp mas antiguo (opcional)"
-        />
-      </div>
-      <div class="space-y-2">
-        <p class="text-sm text-[var(--wa-text-muted)]">Oldest Message Key (opcional, JSON):</p>
-        <UTextarea
-          v-model="oldestMsgKeyJson"
-          placeholder='{"remoteJid": "...", "id": "...", "fromMe": false}'
-          :rows="3"
-          class="font-mono text-sm"
+          class="w-48"
         />
       </div>
+
+      <!-- Action Button -->
       <UButton
         :loading="loading"
         :disabled="!instanceId || !count"
         @click="fetchHistory"
+        color="primary"
       >
-        Solicitar Historial
+        Solicitar {{ count }} mensajes del historial
       </UButton>
+
+      <!-- Advanced Mode Toggle -->
+      <div class="pt-4 border-t border-[var(--wa-border)]">
+        <UCheckbox v-model="showAdvanced" label="Modo avanzado (JSON manual)" />
+      </div>
+
+      <!-- Advanced Mode Fields -->
+      <div v-if="showAdvanced" class="space-y-4 p-4 rounded bg-[var(--wa-bg-hover)]">
+        <p class="text-xs text-[var(--wa-text-muted)]">
+          Estos campos permiten especificar manualmente el mensaje de referencia para la sincronizacion.
+        </p>
+        <div class="grid grid-cols-2 gap-4">
+          <UInput
+            v-model.number="manualTimestamp"
+            type="number"
+            placeholder="Timestamp (segundos)"
+          />
+        </div>
+        <div class="space-y-2">
+          <label class="text-sm text-[var(--wa-text-muted)]">Message Key (JSON):</label>
+          <UTextarea
+            v-model="oldestMsgKeyJson"
+            placeholder='{"remoteJid": "...", "id": "...", "fromMe": false}'
+            :rows="3"
+            class="font-mono text-sm"
+          />
+        </div>
+      </div>
     </div>
   </div>
 </template>
 
 <script setup lang="ts">
+interface Chat {
+  id: string
+  jid: string
+  name: string
+  isGroup: boolean
+}
+
+interface OldestMessage {
+  hasMessages: boolean
+  messageKey: { remoteJid: string; id: string; fromMe: boolean } | null
+  timestamp: number | null
+}
+
 const props = defineProps<{
   instanceId: string | null
 }>()
@@ -49,23 +111,104 @@ const emit = defineEmits<{
   (e: 'response', data: any): void
 }>()
 
-const count = ref<number>(50)
-const oldestMsgTimestamp = ref<number | null>(null)
-const oldestMsgKeyJson = ref('')
+const count = ref<number>(100)
 const loading = ref(false)
+const showAdvanced = ref(false)
+const oldestMsgKeyJson = ref('')
+const manualTimestamp = ref<number | null>(null)
+
+// Chat selection
+const chats = ref<Chat[]>([])
+const selectedChat = ref<{ label: string; value: string; jid: string } | null>(null)
+const loadingChats = ref(false)
+const oldestMessage = ref<OldestMessage | null>(null)
+const loadingOldest = ref(false)
+
+// Computed chat options for select menu
+const chatOptions = computed(() =>
+  chats.value.map(chat => ({
+    label: chat.name || chat.jid.split('@')[0],
+    value: chat.id,
+    jid: chat.jid
+  }))
+)
+
+// Load chats when instanceId changes
+watch(() => props.instanceId, async (instanceId) => {
+  if (!instanceId) {
+    chats.value = []
+    selectedChat.value = null
+    return
+  }
+
+  loadingChats.value = true
+  try {
+    chats.value = await $fetch<Chat[]>(`/api/messages/${instanceId}/chats`)
+  } catch (e) {
+    console.error('Error loading chats:', e)
+    chats.value = []
+  } finally {
+    loadingChats.value = false
+  }
+}, { immediate: true })
+
+// Load oldest message when chat is selected
+watch(selectedChat, async (chat) => {
+  if (!chat || !props.instanceId) {
+    oldestMessage.value = null
+    return
+  }
+
+  loadingOldest.value = true
+  try {
+    oldestMessage.value = await $fetch<OldestMessage>(
+      `/api/messages/${props.instanceId}/${chat.value}/oldest`
+    )
+
+    // Auto-populate JSON field if not in advanced mode
+    if (oldestMessage.value?.hasMessages && oldestMessage.value.messageKey) {
+      oldestMsgKeyJson.value = JSON.stringify(oldestMessage.value.messageKey, null, 2)
+      manualTimestamp.value = oldestMessage.value.timestamp
+    } else {
+      oldestMsgKeyJson.value = ''
+      manualTimestamp.value = null
+    }
+  } catch (e) {
+    console.error('Error loading oldest message:', e)
+    oldestMessage.value = null
+  } finally {
+    loadingOldest.value = false
+  }
+})
+
+// Format timestamp to readable date
+const formatDate = (timestamp: number | null) => {
+  if (!timestamp) return 'N/A'
+  return new Date(timestamp * 1000).toLocaleString()
+}
 
 const fetchHistory = async () => {
   loading.value = true
   try {
     let oldestMsgKey = undefined
-    if (oldestMsgKeyJson.value.trim()) {
-      try {
-        oldestMsgKey = JSON.parse(oldestMsgKeyJson.value)
-      } catch {
-        emit('response', { success: false, error: 'Invalid JSON for oldestMsgKey' })
-        loading.value = false
-        return
+    let oldestMsgTimestamp = undefined
+
+    if (showAdvanced.value) {
+      // Use manual JSON input
+      if (oldestMsgKeyJson.value.trim()) {
+        try {
+          oldestMsgKey = JSON.parse(oldestMsgKeyJson.value)
+        } catch {
+          emit('response', { success: false, error: 'Invalid JSON for oldestMsgKey' })
+          loading.value = false
+          return
+        }
       }
+      oldestMsgTimestamp = manualTimestamp.value || undefined
+    } else if (oldestMessage.value?.hasMessages) {
+      // Use auto-detected oldest message
+      oldestMsgKey = oldestMessage.value.messageKey
+      oldestMsgTimestamp = oldestMessage.value.timestamp
     }
 
     const result = await $fetch('/api/debug/history/fetch', {
@@ -74,7 +217,7 @@ const fetchHistory = async () => {
         instanceId: props.instanceId,
         count: count.value,
         oldestMsgKey,
-        oldestMsgTimestamp: oldestMsgTimestamp.value || undefined
+        oldestMsgTimestamp
       }
     })
     emit('response', result)
diff --git a/app/pages/messages/index.vue b/app/pages/messages/index.vue
index 44c13e3..f2b79fd 100644
--- a/app/pages/messages/index.vue
+++ b/app/pages/messages/index.vue
@@ -188,6 +188,32 @@
               </button>
             </div>
 
+            <!-- Load from WhatsApp when local DB is exhausted -->
+            <div
+              v-else-if="!hasMoreMessages && !loadingWhatsAppHistory"
+              class="flex flex-col items-center py-3 gap-2"
+            >
+              <span class="text-xs text-[var(--wa-text-muted)]">
+                No hay mas mensajes en la base de datos
+              </span>
+              <button
+                class="text-xs px-3 py-1.5 rounded bg-[var(--wa-green)] text-white hover:opacity-90 transition-opacity"
+                @click="fetchWhatsAppHistory"
+              >
+                Cargar historial de WhatsApp
+              </button>
+            </div>
+
+            <div
+              v-else-if="loadingWhatsAppHistory"
+              class="flex flex-col items-center py-3 gap-2"
+            >
+              <UIcon name="i-lucide-loader-2" class="w-5 h-5 animate-spin text-[var(--wa-green)]" />
+              <span class="text-xs text-[var(--wa-text-muted)]">
+                Solicitando historial de WhatsApp...
+              </span>
+            </div>
+
             <MessagesMessageBubble
               v-for="message in reversedMessages"
               :key="message.id"
@@ -244,6 +270,7 @@ const messages = ref<any[]>([])
 const loadingChats = ref(false)
 const loadingMessages = ref(false)
 const loadingMore = ref(false)
+const loadingWhatsAppHistory = ref(false)
 const hasMoreMessages = ref(true)
 const showDebugPanel = ref(false)
 const showChatsDebug = ref(false)
@@ -360,6 +387,56 @@ const handleScroll = () => {
   }
 }
 
+// Fetch message history from WhatsApp (when local DB is exhausted)
+const fetchWhatsAppHistory = async () => {
+  if (!selectedInstance.value?.value || !selectedChat.value) return
+
+  loadingWhatsAppHistory.value = true
+  try {
+    const instanceId = selectedInstance.value.value
+    const chatId = selectedChat.value.id
+
+    // Get the oldest message from local DB
+    const oldest = await $fetch<{
+      hasMessages: boolean
+      messageKey: { remoteJid: string; id: string; fromMe: boolean } | null
+      timestamp: number | null
+    }>(`/api/messages/${instanceId}/${chatId}/oldest`)
+
+    // Request history from WhatsApp
+    if (!oldest.hasMessages) {
+      // No messages in DB, request without reference
+      await $fetch('/api/debug/history/fetch', {
+        method: 'POST',
+        body: {
+          instanceId,
+          count: 100
+        }
+      })
+    } else {
+      // Request messages older than the oldest in DB
+      await $fetch('/api/debug/history/fetch', {
+        method: 'POST',
+        body: {
+          instanceId,
+          count: 100,
+          oldestMsgKey: oldest.messageKey,
+          oldestMsgTimestamp: oldest.timestamp
+        }
+      })
+    }
+
+    // Wait for history sync to complete and reload
+    await new Promise(r => setTimeout(r, 3000))
+    await reloadMessages()
+    hasMoreMessages.value = true
+  } catch (e) {
+    console.error('Error fetching WhatsApp history:', e)
+  } finally {
+    loadingWhatsAppHistory.value = false
+  }
+}
+
 // Computed presence text for current chat
 const currentChatPresence = computed(() => {
   if (!selectedChat.value?.jid) return null
diff --git a/server/api/messages/[instanceId]/[chatId]/oldest.get.ts b/server/api/messages/[instanceId]/[chatId]/oldest.get.ts
new file mode 100644
index 0000000..86b9f63
--- /dev/null
+++ b/server/api/messages/[instanceId]/[chatId]/oldest.get.ts
@@ -0,0 +1,65 @@
+/**
+ * GET /api/messages/:instanceId/:chatId/oldest
+ * Get the oldest message from a chat for use with fetchMessageHistory
+ */
+import { query } from '../../../../utils/database'
+
+interface ChatRow {
+  jid: string
+}
+
+interface MessageRow {
+  message_id: string
+  from_me: boolean
+  timestamp: Date
+}
+
+export default defineEventHandler(async (event) => {
+  const username = getHeader(event, 'x-authentik-username')
+  if (!username) {
+    throw createError({ statusCode: 401, message: 'Unauthorized' })
+  }
+
+  const instanceId = getRouterParam(event, 'instanceId')
+  const chatId = getRouterParam(event, 'chatId')
+
+  // Get chat info (jid)
+  const chatResult = await query<ChatRow>(
+    'SELECT jid FROM chats WHERE id = $1 AND instance_id = $2',
+    [chatId, instanceId]
+  )
+
+  if (!chatResult.rows.length) {
+    throw createError({ statusCode: 404, message: 'Chat not found' })
+  }
+
+  // Get oldest message
+  const oldestResult = await query<MessageRow>(
+    `SELECT message_id, from_me, timestamp
+     FROM messages
+     WHERE chat_id = $1
+     ORDER BY timestamp ASC
+     LIMIT 1`,
+    [chatId]
+  )
+
+  if (!oldestResult.rows.length) {
+    return {
+      hasMessages: false,
+      messageKey: null,
+      timestamp: null
+    }
+  }
+
+  const oldest = oldestResult.rows[0]
+
+  return {
+    hasMessages: true,
+    messageKey: {
+      remoteJid: chatResult.rows[0].jid,
+      id: oldest.message_id,
+      fromMe: oldest.from_me
+    },
+    timestamp: Math.floor(new Date(oldest.timestamp).getTime() / 1000)
+  }
+})