diff --git a/Endpoints/HistoryEndpoint.cs b/Endpoints/HistoryEndpoint.cs
index 99ab069..fa3a348 100644
--- a/Endpoints/HistoryEndpoint.cs
+++ b/Endpoints/HistoryEndpoint.cs
@@ -34,9 +34,26 @@ public static class HistoryEndpoint
         }
 
         const int messageLimit = 500;
+        var beforeStr = ctx.Request.Query["beforeId"].FirstOrDefault();
+        var beforeId = long.TryParse(beforeStr, out var b) ? b : 0;
 
         var totalCount = await db.GetActiveMessageCount(sessionId);
-        var messages = await db.GetLatestActiveMessages(sessionId, messageLimit);
+
+        List<MessageRecord> messages;
+        if (beforeId > 0)
+        {
+            messages = await db.GetActiveMessagesBeforeId(sessionId, beforeId, messageLimit);
+        }
+        else
+        {
+            messages = await db.GetLatestActiveMessages(sessionId, messageLimit);
+        }
+
+        // Zähle wie viele Nachrichten es VOR der ältesten geladenen noch gibt
+        var oldestLoadedId = messages.Count > 0 ? messages[0].Id : 0;
+        var remainingOlder = oldestLoadedId > 0
+            ? await db.GetActiveMessageCountBeforeId(sessionId, oldestLoadedId)
+            : 0;
 
         // Nach Chain gruppieren (Reihenfolge beibehalten)
         var chainIds = messages.Select(m => m.ChainId).Distinct().ToList();
@@ -54,7 +71,8 @@ public static class HistoryEndpoint
         await ctx.Response.WriteAsJsonAsync(new
         {
             entries = result,
-            hasMore = totalCount > messageLimit,
+            hasMore = remainingOlder > 0,
+            remainingCount = remainingOlder,
             totalCount,
             loadedCount = messages.Count
         });
diff --git a/Services/DatabaseService.cs b/Services/DatabaseService.cs
index 9e988ea..6a74998 100644
--- a/Services/DatabaseService.cs
+++ b/Services/DatabaseService.cs
@@ -514,6 +514,28 @@ public class DatabaseService
         return messages.Reverse().ToList();
     }
 
+    public async Task<int> GetActiveMessageCountBeforeId(string sessionId, long beforeId)
+    {
+        using var conn = CreateConnection();
+        return await conn.ExecuteScalarAsync<int>(@"
+            SELECT COUNT(*) FROM messages m
+            JOIN chains c ON m.chain_id = c.chain_id
+            WHERE m.id < @beforeId AND c.archive_id IS NULL AND c.session_id = @sessionId",
+            new { sessionId, beforeId });
+    }
+
+    public async Task<List<MessageRecord>> GetActiveMessagesBeforeId(string sessionId, long beforeId, int limit)
+    {
+        using var conn = CreateConnection();
+        var messages = await conn.QueryAsync<MessageRecord>(@"
+            SELECT m.* FROM messages m
+            JOIN chains c ON m.chain_id = c.chain_id
+            WHERE m.id < @beforeId AND c.archive_id IS NULL AND c.session_id = @sessionId
+            ORDER BY m.id DESC LIMIT @limit",
+            new { sessionId, beforeId, limit });
+        return messages.Reverse().ToList();
+    }
+
     public async Task<IEnumerable<MessageRecord>> GetActiveMessagesAfterId(string sessionId, long afterId, int limit = 200)
     {
         using var conn = CreateConnection();
diff --git a/wwwroot/js/api.js b/wwwroot/js/api.js
index 9ea1bcb..76cca49 100644
--- a/wwwroot/js/api.js
+++ b/wwwroot/js/api.js
@@ -43,8 +43,10 @@ async function apiDeleteAgent(agentId) {
   return fetch(`/api/agents/${agentId}`, { method: 'DELETE' });
 }
 
-async function apiHistory(sessionId) {
-  const resp = await fetch(`/api/history?sessionId=${sessionId}`);
+async function apiHistory(sessionId, beforeId) {
+  let url = `/api/history?sessionId=${sessionId}`;
+  if (beforeId) url += `&beforeId=${beforeId}`;
+  const resp = await fetch(url);
   return resp.json();
 }
 
diff --git a/wwwroot/js/chat.js b/wwwroot/js/chat.js
index 7f3df8f..3cf74f1 100644
--- a/wwwroot/js/chat.js
+++ b/wwwroot/js/chat.js
@@ -62,6 +62,8 @@ async function clearChat() {
   chatEl().innerHTML = '';
   lastKnownMessageId = 0;
   loadedArchiveCount = 0;
+  _oldestLoadedMessageId = 0;
+  _hasMoreOlderMessages = false;
   clearReply();
 
   setMeta(`Archiviert: ${archive.chainCount} Chains, ${archive.messageCount} Messages`);
diff --git a/wwwroot/js/history.js b/wwwroot/js/history.js
index 82b0528..7027c03 100644
--- a/wwwroot/js/history.js
+++ b/wwwroot/js/history.js
@@ -1,26 +1,30 @@
 // ── History Loading ──
 
 let lastKnownMessageId = 0;
+let _oldestLoadedMessageId = 0;
+let _hasMoreOlderMessages = false;
 let historyPollInterval = null;
 let loadedArchiveCount = 0;
 
 async function loadHistory() {
   try {
     const sid = getCurrentSessionId();
-    const archives = await apiListArchives(sid);
-    if (archives.length > 0) {
-      showArchiveLoadButton();
-    }
 
     const data = await apiHistory(sid);
     const entries = data.entries || [];
 
+    // Älteste geladene Message-ID merken für Nachladen
+    _hasMoreOlderMessages = data.hasMore;
+    _oldestLoadedMessageId = _findOldestMessageId(entries);
+
     if (data.hasMore) {
-      const skipped = data.totalCount - data.loadedCount;
-      const info = document.createElement('div');
-      info.className = 'msg system-info';
-      info.innerHTML = `<i class="fa fa-info-circle"></i> ${skipped} ältere Nachrichten nicht geladen`;
-      chatEl().appendChild(info);
+      showOlderMessagesButton(data.remainingCount);
+    } else {
+      // Keine älteren Nachrichten mehr → Archiv-Button anzeigen falls vorhanden
+      const archives = await apiListArchives(sid);
+      if (archives.length > 0) {
+        showArchiveLoadButton();
+      }
     }
 
     for (const entry of entries) {
@@ -36,6 +40,150 @@ async function loadHistory() {
   }
 }
 
+async function loadOlderMessages() {
+  if (!_hasMoreOlderMessages || !_oldestLoadedMessageId) return;
+
+  const btn = chatEl().querySelector('.older-messages-btn');
+  if (btn) {
+    btn.disabled = true;
+    btn.innerHTML = '<i class="fa fa-hourglass-half"></i> Wird geladen...';
+  }
+
+  try {
+    const sid = getCurrentSessionId();
+    const data = await apiHistory(sid, _oldestLoadedMessageId);
+    const entries = data.entries || [];
+
+    _hasMoreOlderMessages = data.hasMore;
+    const newOldest = _findOldestMessageId(entries);
+    if (newOldest > 0) _oldestLoadedMessageId = newOldest;
+
+    // Button entfernen
+    removeOlderMessagesButton();
+
+    // Scroll-Position merken
+    const chat = chatEl();
+    const oldScrollHeight = chat.scrollHeight;
+
+    // Nachrichten oben einfügen (vor dem ersten .msg Element)
+    const fragment = document.createDocumentFragment();
+    for (const entry of entries) {
+      _renderMessagesIntoFragment(fragment, entry.messages);
+      if (entry.chain && isChainMetaVisible(entry.chain)) {
+        const badges = buildMetaBadges(entry.chain);
+        const metaDiv = document.createElement('div');
+        metaDiv.className = 'chain-meta';
+        metaDiv.innerHTML = badges.map(b => '<span class="chain-meta-badge">' + esc(b) + '</span>').join('');
+        fragment.appendChild(metaDiv);
+      }
+    }
+
+    // Einfügen: vor dem ersten .msg oder .chain-meta Element
+    const firstMsg = chat.querySelector('.msg, .chain-meta, .tool-box');
+    if (firstMsg) {
+      chat.insertBefore(fragment, firstMsg);
+    } else {
+      chat.appendChild(fragment);
+    }
+
+    // Neuen Button oder Archiv-Button anzeigen
+    if (data.hasMore) {
+      showOlderMessagesButton(data.remainingCount);
+    } else {
+      const archives = await apiListArchives(sid);
+      if (archives.length > 0) {
+        showArchiveLoadButton();
+      }
+    }
+
+    // Scroll-Position beibehalten
+    const newScrollHeight = chat.scrollHeight;
+    chat.scrollTop += (newScrollHeight - oldScrollHeight);
+
+  } catch (e) {
+    console.error('Ältere Nachrichten laden fehlgeschlagen:', e);
+    if (_hasMoreOlderMessages) {
+      showOlderMessagesButton(0);
+    }
+  }
+}
+
+function _findOldestMessageId(entries) {
+  for (const entry of entries) {
+    if (entry.messages && entry.messages.length > 0) {
+      return entry.messages[0].id;
+    }
+  }
+  return 0;
+}
+
+function _renderMessagesIntoFragment(fragment, msgs) {
+  for (const msg of msgs) {
+    const div = document.createElement('div');
+    switch (msg.type) {
+      case 'text':
+        if (msg.role === 'user') {
+          div.className = 'msg user' + (msg.isMarked ? ' marked' : '');
+          div.dataset.role = 'user';
+          div.dataset.timestamp = msg.createdAt || '';
+          if (msg.id) div.dataset.messageId = msg.id;
+          renderUserContent(div, msg.content);
+          _addReplyButton(div);
+          _addMarkButton(div, msg.id, msg.isMarked);
+          fragment.appendChild(div);
+          if (msg.attachmentCount > 0) {
+            let names = [];
+            try { if (msg.attachmentNames) names = JSON.parse(msg.attachmentNames); } catch {}
+            const nameList = names.filter(n => n).join(', ');
+            const ind = document.createElement('div');
+            ind.className = 'attachment-indicator';
+            ind.innerHTML = `<i class="fa fa-paperclip"></i> ${msg.attachmentCount} Datei${msg.attachmentCount > 1 ? 'en' : ''}` + (nameList ? `: ${esc(nameList)}` : '');
+            ind.style.cursor = 'pointer';
+            ind.title = 'Klicken zum Anzeigen';
+            ind.addEventListener('click', () => loadAndShowAttachments(msg.id, ind));
+            div.appendChild(ind);
+          }
+        } else if (msg.role === 'assistant') {
+          div.className = 'msg assistant markdown' + (msg.isMarked ? ' marked' : '');
+          div.dataset.role = 'assistant';
+          div.dataset.timestamp = msg.createdAt || '';
+          if (msg.id) div.dataset.messageId = msg.id;
+          div.innerHTML = renderMarkdown(msg.content);
+          _addReplyButton(div);
+          _addMarkButton(div, msg.id, msg.isMarked);
+          fragment.appendChild(div);
+        }
+        break;
+      case 'tool_use':
+        if (!isToolVisible(msg.toolName)) continue;
+        div.className = 'tool-box';
+        renderToolBoxContent(div, msg.toolName, msg.content, null, false);
+        fragment.appendChild(div);
+        break;
+      case 'tool_result': {
+        const prevBoxes = fragment.querySelectorAll('.tool-box');
+        const lastToolBox = prevBoxes[prevBoxes.length - 1];
+        if (lastToolBox && !lastToolBox.querySelector('.tool-result')) {
+          const rd = document.createElement('div');
+          rd.className = 'tool-result' + (msg.isError ? ' tool-error' : '');
+          rd.textContent = truncate(msg.content || '', 300);
+          rd.hidden = true;
+          lastToolBox.appendChild(rd);
+        }
+        continue;
+      }
+      case 'error':
+        div.className = 'msg system-info';
+        div.style.color = 'var(--dangerous)';
+        div.textContent = (msg.content || '').trim();
+        fragment.appendChild(div);
+        break;
+      default:
+        continue;
+    }
+  }
+}
+
 function renderMessages(msgs, addToConversation) {
   for (const msg of msgs) {
     if (msg.id > lastKnownMessageId) lastKnownMessageId = msg.id;
diff --git a/wwwroot/js/pages/chat-page.js b/wwwroot/js/pages/chat-page.js
index 6fbbb51..beff8a1 100644
--- a/wwwroot/js/pages/chat-page.js
+++ b/wwwroot/js/pages/chat-page.js
@@ -239,6 +239,8 @@ registerPage('chat', {
     messages.length = 0;
     lastKnownMessageId = 0;
     loadedArchiveCount = 0;
+    _oldestLoadedMessageId = 0;
+    _hasMoreOlderMessages = false;
     isStreaming = false;
 
     await loadHistory();
diff --git a/wwwroot/js/ui.js b/wwwroot/js/ui.js
index 2070b53..acb7884 100644
--- a/wwwroot/js/ui.js
+++ b/wwwroot/js/ui.js
@@ -650,10 +650,26 @@ function setMetaHtml(html) {
   metaEl().innerHTML = html;
 }
 
+// ── Older Messages Button ──
+
+function showOlderMessagesButton(remainingCount) {
+  removeOlderMessagesButton();
+  const btn = document.createElement('button');
+  btn.className = 'archive-load-btn older-messages-btn';
+  btn.innerHTML = '<i class="fa fa-arrow-up"></i> ' + remainingCount + ' ältere Nachrichten laden';
+  btn.addEventListener('click', () => loadOlderMessages());
+  chatEl().prepend(btn);
+}
+
+function removeOlderMessagesButton() {
+  const btn = chatEl().querySelector('.older-messages-btn');
+  if (btn) btn.remove();
+}
+
 // ── Archive Button ──
 
 function showArchiveLoadButton() {
-  const existing = chatEl().querySelector('.archive-load-btn');
+  const existing = chatEl().querySelector('.archive-load-btn:not(.older-messages-btn)');
   if (existing) existing.remove();
 
   const btn = document.createElement('button');
@@ -661,11 +677,16 @@ function showArchiveLoadButton() {
   btn.innerHTML = '<i class="fa fa-archive"></i> Archivierte Nachrichten laden';
   btn.addEventListener('click', loadLatestArchive);
 
-  // Immer ganz oben im Chat
-  chatEl().prepend(btn);
+  // Immer ganz oben im Chat (aber nach dem older-messages-btn falls vorhanden)
+  const olderBtn = chatEl().querySelector('.older-messages-btn');
+  if (olderBtn) {
+    olderBtn.after(btn);
+  } else {
+    chatEl().prepend(btn);
+  }
 }
 
 function removeArchiveLoadButton() {
-  const btn = chatEl().querySelector('.archive-load-btn');
-  if (btn) btn.remove();
+  const btns = chatEl().querySelectorAll('.archive-load-btn:not(.older-messages-btn)');
+  btns.forEach(b => b.remove());
 }