diff --git a/interface/web/src/App.jsx b/interface/web/src/App.jsx
index f96821d..25996d7 100644
--- a/interface/web/src/App.jsx
+++ b/interface/web/src/App.jsx
@@ -4,6 +4,7 @@ import { Playbook } from "./Playbook";
 import { Models } from "./Models";
 import { Settings } from "./Settings";
 import { Memory } from "./Memory";
+import { Documents } from "./Documents";
 import { Logs } from "./Logs";
 
 import { API_BASE } from "./config";
@@ -128,6 +129,15 @@ function App() {
     }
   };
 
+  // Download ShareGPT JSONL — one conversation if convId given, else all.
+  const exportConversations = (e, convId) => {
+    if (e) e.stopPropagation();
+    const url = convId
+      ? `${API_BASE}/conversations/export?conversation_id=${encodeURIComponent(convId)}`
+      : `${API_BASE}/conversations/export`;
+    window.open(url, "_blank");
+  };
+
   const deleteConversation = async (e, conversationId) => {
     e.stopPropagation();
     if (!window.confirm("Delete this conversation?")) return;
@@ -149,6 +159,7 @@ function App() {
     { key: "playbook", label: "📖 Playbooks" },
     { key: "models", label: "🤖 Models", badge: isModelPulling },
     { key: "memory", label: "🧠 Memory" },
+    { key: "documents", label: "📄 Documents" },
     { key: "logs", label: "📜 Logs" },
     { key: "settings", label: "⚙️ Settings" },
   ];
@@ -295,21 +306,39 @@ function App() {
         }}>
           <div style={{ display: "flex", justifyContent: "space-between", alignItems: "center", marginBottom: "0.5rem", flexShrink: 0 }}>
             <span style={{ fontSize: "0.75rem", color: "#888", textTransform: "uppercase", letterSpacing: "0.05em" }}>Chats</span>
-            <button
-              onClick={startNewChat}
-              title="New chat"
-              style={{
-                padding: "0.2rem 0.55rem",
-                background: "#161616",
-                color: "#bbb",
-                border: "1px solid #2a2a2a",
-                borderRadius: "6px",
-                cursor: "pointer",
-                fontSize: "0.75rem",
-              }}
-            >
-              + New
-            </button>
+            <div style={{ display: "flex", gap: "0.35rem" }}>
+              <button
+                onClick={() => exportConversations(null, null)}
+                title="Export all conversations (ShareGPT JSONL)"
+                disabled={conversations.length === 0}
+                style={{
+                  padding: "0.2rem 0.5rem",
+                  background: "#161616",
+                  color: conversations.length === 0 ? "#555" : "#bbb",
+                  border: "1px solid #2a2a2a",
+                  borderRadius: "6px",
+                  cursor: conversations.length === 0 ? "default" : "pointer",
+                  fontSize: "0.75rem",
+                }}
+              >
+                ⤓ Export
+              </button>
+              <button
+                onClick={startNewChat}
+                title="New chat"
+                style={{
+                  padding: "0.2rem 0.55rem",
+                  background: "#161616",
+                  color: "#bbb",
+                  border: "1px solid #2a2a2a",
+                  borderRadius: "6px",
+                  cursor: "pointer",
+                  fontSize: "0.75rem",
+                }}
+              >
+                + New
+              </button>
+            </div>
           </div>
           <input
             type="text"
@@ -372,6 +401,22 @@ function App() {
                     </div>
                     {isHover && (
                       <>
+                        <button
+                          onClick={(e) => exportConversations(e, conv.id)}
+                          title="Export this conversation"
+                          style={{
+                            padding: "0.15rem 0.4rem",
+                            background: "transparent",
+                            color: "#888",
+                            border: "1px solid #333",
+                            borderRadius: "4px",
+                            cursor: "pointer",
+                            fontSize: "0.7rem",
+                            flexShrink: 0,
+                          }}
+                        >
+                          📤
+                        </button>
                         <button
                           onClick={(e) => renameConversation(e, conv)}
                           title="Rename"
@@ -434,6 +479,7 @@ function App() {
         )}
         {currentPage === "playbook" && <Playbook />}
         {currentPage === "memory" && <Memory />}
+        {currentPage === "documents" && <Documents />}
         {currentPage === "logs" && <Logs />}
         {currentPage === "settings" && <Settings />}
       </main>
diff --git a/interface/web/src/Chatbot.jsx b/interface/web/src/Chatbot.jsx
index 1477b84..ceb4070 100644
--- a/interface/web/src/Chatbot.jsx
+++ b/interface/web/src/Chatbot.jsx
@@ -14,6 +14,46 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
   const [copiedIdx, setCopiedIdx] = useState(null);
   const [lastStats, setLastStats] = useState(null);
   const [memoryToast, setMemoryToast] = useState(null);
+  const [images, setImages] = useState([]); // {name, b64} for vision models
+  const [activeTool, setActiveTool] = useState(null); // playbook tool currently running
+  const [editingIdx, setEditingIdx] = useState(null); // user message being edited
+  const [editText, setEditText] = useState("");
+  const [listening, setListening] = useState(false); // mic dictation active
+  const [speakingIdx, setSpeakingIdx] = useState(null); // message being read aloud
+  const recognitionRef = useRef(null);
+
+  // Web Speech API — browser-native, no backend/model. Absent on unsupported browsers.
+  const SpeechRec = typeof window !== "undefined" && (window.SpeechRecognition || window.webkitSpeechRecognition);
+  const ttsSupported = typeof window !== "undefined" && "speechSynthesis" in window;
+
+  const toggleMic = () => {
+    if (!SpeechRec) return;
+    if (listening) { recognitionRef.current?.stop(); return; }
+    const rec = new SpeechRec();
+    rec.lang = "en-US";
+    rec.interimResults = false;
+    rec.onresult = (e) => {
+      const text = Array.from(e.results).map(r => r[0].transcript).join(" ").trim();
+      if (text) setInput(prev => (prev ? prev + " " : "") + text);
+    };
+    rec.onend = () => setListening(false);
+    rec.onerror = () => setListening(false);
+    recognitionRef.current = rec;
+    setListening(true);
+    rec.start();
+  };
+
+  // Read a reply aloud (light markdown strip so symbols aren't spoken).
+  const speak = (idx, text) => {
+    if (!ttsSupported) return;
+    window.speechSynthesis.cancel();
+    if (speakingIdx === idx) { setSpeakingIdx(null); return; }
+    const clean = text.replace(/[*_`#>]/g, "").replace(/\[(.*?)\]\(.*?\)/g, "$1");
+    const u = new SpeechSynthesisUtterance(clean);
+    u.onend = () => setSpeakingIdx(null);
+    setSpeakingIdx(idx);
+    window.speechSynthesis.speak(u);
+  };
 
   const abortRef = useRef(null);
   const messagesEndRef = useRef(null);
@@ -78,19 +118,22 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
     setConversationId(crypto.randomUUID());
   };
 
-  const sendMessage = async () => {
-    if (!input.trim() || loading) return;
-
-    const userMessage = input.trim();
-    setInput("");
-
-    // Add user message
-    setMessages(prev => [...prev, { role: "user", content: userMessage }]);
-
-    // Prepare assistant placeholder
-    const assistantIndex = messages.length + 1;
-    setMessages(prev => [...prev, { role: "assistant", content: "" }]);
+  const onImagePick = (e) => {
+    const files = Array.from(e.target.files || []);
+    files.forEach(file => {
+      const reader = new FileReader();
+      reader.onload = () => {
+        const b64 = String(reader.result || "").split(",")[1]; // strip data: prefix
+        if (b64) setImages(prev => [...prev, { name: file.name, b64 }]);
+      };
+      reader.readAsDataURL(file);
+    });
+    e.target.value = "";
+  };
 
+  // Shared streaming core: POST /chat/stream and fold tokens into the assistant
+  // message at `assistantIndex`. Used by send, regenerate, and edit-and-resend.
+  const streamAssistant = async ({ message, history, images: imgs, assistantIndex }) => {
     setLoading(true);
 
     // Abort previous stream if still open
@@ -99,16 +142,14 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
     abortRef.current = controller;
 
     try {
-      // Exclude the empty assistant placeholder that was just appended
-      const historySnapshot = messages.filter(m => m.content.trim() !== "");
-
       const response = await fetch(`${API_BASE}/chat/stream`, {
         method: "POST",
         headers: { "Content-Type": "application/json" },
         body: JSON.stringify({
-          message: userMessage,
+          message,
           conversation_id: conversationId,
-          history: historySnapshot.map(m => ({ role: m.role, content: m.content })),
+          history,
+          ...(imgs && imgs.length ? { images: imgs } : {}),
         }),
         signal: controller.signal,
       });
@@ -169,10 +210,16 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
               pendingEventType = null;
               continue;
             }
+            if (pendingEventType === "status") {
+              try { setActiveTool(JSON.parse(payload).tool); } catch { /* ignore */ }
+              pendingEventType = null;
+              continue;
+            }
             if (pendingEventType === "done") {
               // Answer is complete; re-enable input while the backend finishes
               // slow post-processing (title, memory) on the still-open stream.
               setLoading(false);
+              setActiveTool(null);
               pendingEventType = null;
               continue;
             }
@@ -197,6 +244,7 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
             let token = payload;
             try { token = JSON.parse(payload); } catch { /* plain text fallback */ }
 
+            if (activeTool) setActiveTool(null); // tokens started -> tools done
             setMessages(prev => {
               const updated = [...prev];
               updated[assistantIndex] = {
@@ -219,6 +267,54 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
     }
   };
 
+  const histBefore = (index) =>
+    messages.slice(0, index).filter(m => m.content.trim() !== "")
+      .map(m => ({ role: m.role, content: m.content }));
+
+  const sendMessage = async () => {
+    if ((!input.trim() && images.length === 0) || loading) return;
+
+    const userMessage = input.trim();
+    const outImages = images.map(i => i.b64);
+    setInput("");
+    setImages([]);
+
+    // Note any attached images so image-only turns aren't blank
+    const shownContent = outImages.length
+      ? `${userMessage}${userMessage ? "\n\n" : ""}📷 ${outImages.length} image${outImages.length === 1 ? "" : "s"} attached`
+      : userMessage;
+    const history = histBefore(messages.length);
+    const assistantIndex = messages.length + 1;
+    setMessages(prev => [...prev, { role: "user", content: shownContent }, { role: "assistant", content: "" }]);
+    await streamAssistant({ message: userMessage, history, images: outImages, assistantIndex });
+  };
+
+  const regenerate = async () => {
+    if (loading) return;
+    const lastUserIdx = messages.map(m => m.role).lastIndexOf("user");
+    if (lastUserIdx < 0) return;
+    const userMessage = messages[lastUserIdx].content;
+    const history = histBefore(lastUserIdx);
+    const base = messages.slice(0, lastUserIdx + 1); // drop the old assistant reply
+    setMessages([...base, { role: "assistant", content: "" }]);
+    await streamAssistant({ message: userMessage, history, images: [], assistantIndex: base.length });
+  };
+
+  const editAndResend = async (index, newText) => {
+    if (loading || !newText.trim()) return;
+    const history = histBefore(index);
+    const base = [...messages.slice(0, index), { role: "user", content: newText.trim() }];
+    setEditingIdx(null);
+    setMessages([...base, { role: "assistant", content: "" }]);
+    await streamAssistant({ message: newText.trim(), history, images: [], assistantIndex: base.length });
+  };
+
+  const stopGeneration = () => {
+    if (abortRef.current) abortRef.current.abort();
+    setLoading(false);
+    setActiveTool(null);
+  };
+
   const updateAssistant = (index, text) => {
     setMessages(prev => {
       const updated = [...prev];
@@ -404,33 +500,71 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
                     boxSizing: "border-box",
                   }}
                 >
-                  {msg.role === "user"
+                  {msg.role === "user" && editingIdx === idx ? (
+                    <div style={{ display: "flex", flexDirection: "column", gap: "0.4rem" }}>
+                      <textarea
+                        value={editText}
+                        onChange={e => setEditText(e.target.value)}
+                        rows={3}
+                        style={{ width: "100%", padding: "0.5rem", background: "#0a3a5c", color: "#fff", border: "1px solid #0099ff", borderRadius: "8px", resize: "vertical", boxSizing: "border-box" }}
+                      />
+                      <div style={{ display: "flex", gap: "0.4rem", justifyContent: "flex-end" }}>
+                        <button onClick={() => editAndResend(idx, editText)} disabled={loading || !editText.trim()}
+                          style={{ padding: "0.3rem 0.7rem", fontSize: "0.8rem", background: "#0099ff", color: "#fff", border: "none", borderRadius: "6px", cursor: "pointer" }}>
+                          Save &amp; resend
+                        </button>
+                        <button onClick={() => setEditingIdx(null)}
+                          style={{ padding: "0.3rem 0.7rem", fontSize: "0.8rem", background: "transparent", color: "#cce", border: "1px solid #0099ff", borderRadius: "6px", cursor: "pointer" }}>
+                          Cancel
+                        </button>
+                      </div>
+                    </div>
+                  ) : msg.role === "user"
                     ? <span style={{ whiteSpace: "pre-wrap" }}>{msg.content}</span>
                       : msg.content
                       ? <Markdown content={msg.content} />
                       : <span style={{ color: "#aaa" }}>Thinking...</span>
                   }
                 </div>
-                {msg.content && (
-                  <button
-                    onClick={() => {
-                      navigator.clipboard.writeText(msg.content).then(() => {
-                        setCopiedIdx(idx);
-                        setTimeout(() => setCopiedIdx(null), 1500);
-                      });
-                    }}
-                    style={{
-                      marginTop: "0.25rem",
-                      padding: "0.15rem 0.5rem",
-                      fontSize: "0.7rem",
-                      color: copiedIdx === idx ? "#4caf50" : "#555",
-                      background: "transparent",
-                      border: "none",
-                      cursor: "pointer",
-                    }}
-                  >
-                    {copiedIdx === idx ? "Copied!" : "Copy"}
-                  </button>
+                {msg.content && editingIdx !== idx && (
+                  <div style={{ display: "flex", gap: "0.25rem", marginTop: "0.25rem" }}>
+                    <button
+                      onClick={() => {
+                        navigator.clipboard.writeText(msg.content).then(() => {
+                          setCopiedIdx(idx);
+                          setTimeout(() => setCopiedIdx(null), 1500);
+                        });
+                      }}
+                      style={{ padding: "0.15rem 0.5rem", fontSize: "0.7rem", color: copiedIdx === idx ? "#4caf50" : "#555", background: "transparent", border: "none", cursor: "pointer" }}
+                    >
+                      {copiedIdx === idx ? "Copied!" : "Copy"}
+                    </button>
+                    {msg.role === "user" && !loading && (
+                      <button
+                        onClick={() => { setEditingIdx(idx); setEditText(msg.content); }}
+                        style={{ padding: "0.15rem 0.5rem", fontSize: "0.7rem", color: "#555", background: "transparent", border: "none", cursor: "pointer" }}
+                      >
+                        Edit
+                      </button>
+                    )}
+                    {msg.role === "assistant" && !loading && idx === messages.length - 1 && (
+                      <button
+                        onClick={regenerate}
+                        style={{ padding: "0.15rem 0.5rem", fontSize: "0.7rem", color: "#555", background: "transparent", border: "none", cursor: "pointer" }}
+                      >
+                        ↻ Regenerate
+                      </button>
+                    )}
+                    {msg.role === "assistant" && ttsSupported && (
+                      <button
+                        onClick={() => speak(idx, msg.content)}
+                        title={speakingIdx === idx ? "Stop" : "Read aloud"}
+                        style={{ padding: "0.15rem 0.5rem", fontSize: "0.7rem", color: speakingIdx === idx ? "#4caf50" : "#555", background: "transparent", border: "none", cursor: "pointer" }}
+                      >
+                        {speakingIdx === idx ? "🔊 Stop" : "🔊 Speak"}
+                      </button>
+                    )}
+                  </div>
                 )}
               </div>
             ))
@@ -439,7 +573,34 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
 <div ref={messagesEndRef} />
         </div>
 
+        {activeTool && (
+          <div style={{ marginBottom: "0.5rem", color: "#8ab4ff", fontSize: "0.9rem" }}>
+            🔧 running tool: {activeTool}…
+          </div>
+        )}
+        {images.length > 0 && (
+          <div style={{ display: "flex", flexWrap: "wrap", gap: "0.5rem", marginBottom: "0.5rem" }}>
+            {images.map((img, i) => (
+              <span key={i} style={{ display: "inline-flex", alignItems: "center", gap: "0.4rem", padding: "0.35rem 0.6rem", background: "#1a1a1a", border: "1px solid #2a2a2a", borderRadius: "8px", color: "#ccc", fontSize: "0.85rem" }}>
+                📷 {img.name}
+                <button onClick={() => setImages(prev => prev.filter((_, j) => j !== i))}
+                  style={{ background: "none", border: "none", color: "#ff8a80", cursor: "pointer", padding: 0 }}>✕</button>
+              </span>
+            ))}
+          </div>
+        )}
         <div style={{ display: "flex", gap: "0.75rem", alignItems: "flex-end" }}>
+          <label title="Attach image (needs a vision model)"
+            style={{ padding: "0.9rem", background: "#222", border: "1px solid #333", borderRadius: "10px", cursor: loading ? "default" : "pointer", opacity: loading ? 0.6 : 1, color: "#ccc" }}>
+            📎
+            <input type="file" accept="image/*" multiple onChange={onImagePick} disabled={loading} style={{ display: "none" }} />
+          </label>
+          {SpeechRec && (
+            <button onClick={toggleMic} title={listening ? "Stop dictation" : "Dictate (speech to text)"}
+              style={{ padding: "0.9rem", background: listening ? "#3a1a1a" : "#222", border: "1px solid " + (listening ? "#c0392b" : "#333"), borderRadius: "10px", cursor: "pointer", color: listening ? "#ff8a80" : "#ccc" }}>
+              {listening ? "🔴" : "🎤"}
+            </button>
+          )}
           <textarea
             value={input}
             onChange={e => setInput(e.target.value)}
@@ -460,19 +621,19 @@ export function Chatbot({ conversationId, setConversationId, onConversationChang
             }}
           />
           <button
-            onClick={sendMessage}
-            disabled={loading || !input.trim()}
+            onClick={loading ? stopGeneration : sendMessage}
+            disabled={!loading && !input.trim() && images.length === 0}
             style={{
               padding: "0.9rem 1.5rem",
-              background: loading || !input.trim() ? "#555" : "#007acc",
+              background: loading ? "#c0392b" : (!input.trim() && images.length === 0 ? "#555" : "#007acc"),
               color: "#fff",
               border: "none",
               borderRadius: "8px",
-              cursor: loading || !input.trim() ? "default" : "pointer",
-              opacity: loading || !input.trim() ? 0.6 : 1,
+              cursor: !loading && !input.trim() && images.length === 0 ? "default" : "pointer",
+              opacity: !loading && !input.trim() && images.length === 0 ? 0.6 : 1,
             }}
           >
-            Send
+            {loading ? "Stop" : "Send"}
           </button>
         </div>
       </div>
diff --git a/interface/web/src/Documents.jsx b/interface/web/src/Documents.jsx
new file mode 100644
index 0000000..91092ed
--- /dev/null
+++ b/interface/web/src/Documents.jsx
@@ -0,0 +1,146 @@
+import { useEffect, useState } from "react";
+import { API_BASE } from "./config";
+
+// RAG document manager: upload/paste text, chunked + embedded server-side, then
+// retrieved into the chat system prompt. See synapse/memory/store.py.
+export function Documents() {
+  const [docs, setDocs] = useState([]);
+  const [title, setTitle] = useState("");
+  const [content, setContent] = useState("");
+  const [busy, setBusy] = useState(false);
+  const [message, setMessage] = useState("");
+  const [viewing, setViewing] = useState(null); // {title, chunks} being previewed
+
+  const openDoc = async (doc) => {
+    try {
+      const r = await fetch(`${API_BASE}/documents/${encodeURIComponent(doc.doc_id)}`);
+      if (r.ok) setViewing({ title: doc.title, chunks: (await r.json()).chunks || [] });
+    } catch { /* ignore */ }
+  };
+
+  const load = async () => {
+    try {
+      const r = await fetch(`${API_BASE}/documents`);
+      if (r.ok) setDocs((await r.json()).documents || []);
+    } catch { /* offline — leave list as-is */ }
+  };
+
+  useEffect(() => { load(); }, []);
+
+  const onFile = (e) => {
+    const file = e.target.files?.[0];
+    if (!file) return;
+    const reader = new FileReader();
+    reader.onload = () => {
+      setContent(String(reader.result || ""));
+      if (!title.trim()) setTitle(file.name.replace(/\.[^.]+$/, ""));
+    };
+    reader.readAsText(file);
+    e.target.value = ""; // allow re-selecting the same file
+  };
+
+  const addDoc = async () => {
+    if (!title.trim() || !content.trim()) {
+      setMessage("Title and content are required.");
+      return;
+    }
+    setBusy(true);
+    setMessage("Chunking and embedding…");
+    try {
+      const r = await fetch(`${API_BASE}/documents`, {
+        method: "POST",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify({ title: title.trim(), content }),
+      });
+      if (r.ok) {
+        const d = await r.json();
+        setMessage(`Indexed "${d.title}" (${d.chunks} chunk${d.chunks === 1 ? "" : "s"}).`);
+        setTitle("");
+        setContent("");
+        load();
+      } else {
+        setMessage((await r.json().catch(() => ({}))).detail || "Failed to index.");
+      }
+    } catch (err) {
+      setMessage(`Error: ${err.message}`);
+    } finally {
+      setBusy(false);
+    }
+  };
+
+  const removeDoc = async (docId) => {
+    try {
+      await fetch(`${API_BASE}/documents/${encodeURIComponent(docId)}`, { method: "DELETE" });
+      load();
+    } catch { /* ignore */ }
+  };
+
+  const input = { padding: "0.9rem", background: "#222", color: "#eee", border: "1px solid #333", borderRadius: "10px", width: "100%", boxSizing: "border-box" };
+
+  return (
+    <div style={{ padding: "1.5rem", color: "#eee", maxWidth: "820px" }}>
+      <h2 style={{ marginTop: 0 }}>📄 Documents</h2>
+      <p style={{ color: "#aaa", marginTop: 0 }}>
+        Upload or paste text. It's chunked, embedded, and pulled into chat as source
+        material when a message is relevant.
+      </p>
+
+      <div style={{ display: "flex", flexDirection: "column", gap: "0.7rem", marginBottom: "1.5rem" }}>
+        <input type="text" placeholder="Title" value={title}
+          onChange={e => setTitle(e.target.value)} style={input} />
+        <textarea rows={8} placeholder="Paste text here, or load a .txt/.md file below"
+          value={content} onChange={e => setContent(e.target.value)} style={input} />
+        <div style={{ display: "flex", gap: "0.7rem", alignItems: "center" }}>
+          <input type="file" accept=".txt,.md,.markdown,text/*" onChange={onFile}
+            style={{ color: "#aaa", flex: 1 }} />
+          <button onClick={addDoc} disabled={busy}
+            style={{ padding: "0.9rem 1.5rem", background: busy ? "#555" : "#007acc", color: "#fff", border: "none", borderRadius: "8px", cursor: busy ? "default" : "pointer" }}>
+            {busy ? "Indexing…" : "Add document"}
+          </button>
+        </div>
+        {message && <div style={{ color: "#8ab4ff" }}>{message}</div>}
+      </div>
+
+      {docs.length === 0 ? (
+        <div style={{ color: "#777" }}>No documents yet.</div>
+      ) : (
+        <div style={{ display: "flex", flexDirection: "column", gap: "0.5rem" }}>
+          {docs.map(d => (
+            <div key={d.doc_id} style={{ display: "flex", justifyContent: "space-between", alignItems: "center", padding: "0.8rem 1rem", background: "#1a1a1a", border: "1px solid #2a2a2a", borderRadius: "10px" }}>
+              <div onClick={() => openDoc(d)} style={{ cursor: "pointer", flex: 1 }} title="View chunks">
+                <div style={{ fontWeight: 600 }}>{d.title}</div>
+                <div style={{ color: "#888", fontSize: "0.85rem" }}>{d.chunks} chunk{d.chunks === 1 ? "" : "s"}</div>
+              </div>
+              <button onClick={() => removeDoc(d.doc_id)}
+                style={{ padding: "0.5rem 0.9rem", background: "#2a1a1a", color: "#ff8a80", border: "1px solid #5a2a2a", borderRadius: "8px", cursor: "pointer" }}>
+                Delete
+              </button>
+            </div>
+          ))}
+        </div>
+      )}
+
+      {viewing && (
+        <div onClick={() => setViewing(null)}
+          style={{ position: "fixed", inset: 0, background: "rgba(0,0,0,0.6)", display: "flex", alignItems: "center", justifyContent: "center", zIndex: 100, padding: "2rem" }}>
+          <div onClick={e => e.stopPropagation()}
+            style={{ background: "#1a1a1a", border: "1px solid #333", borderRadius: "12px", maxWidth: "700px", width: "100%", maxHeight: "80vh", display: "flex", flexDirection: "column" }}>
+            <div style={{ display: "flex", justifyContent: "space-between", alignItems: "center", padding: "1rem 1.25rem", borderBottom: "1px solid #2a2a2a" }}>
+              <strong>{viewing.title}</strong>
+              <button onClick={() => setViewing(null)}
+                style={{ background: "none", border: "none", color: "#aaa", fontSize: "1.2rem", cursor: "pointer" }}>✕</button>
+            </div>
+            <div style={{ overflowY: "auto", padding: "1rem 1.25rem" }}>
+              {viewing.chunks.map(c => (
+                <div key={c.chunk_idx} style={{ marginBottom: "1rem" }}>
+                  <div style={{ color: "#666", fontSize: "0.75rem", marginBottom: "0.3rem" }}>chunk {c.chunk_idx + 1}</div>
+                  <div style={{ whiteSpace: "pre-wrap", color: "#ddd", fontSize: "0.9rem", background: "#141414", border: "1px solid #262626", borderRadius: "8px", padding: "0.7rem" }}>{c.text}</div>
+                </div>
+              ))}
+            </div>
+          </div>
+        </div>
+      )}
+    </div>
+  );
+}
diff --git a/interface/web/src/Playbook.jsx b/interface/web/src/Playbook.jsx
index 8706a07..a3e8109 100644
--- a/interface/web/src/Playbook.jsx
+++ b/interface/web/src/Playbook.jsx
@@ -64,6 +64,8 @@ export function Playbook() {
         goal: full.goal || "",
         instructions: full.instructions || "",
         tags: (full.tags || []).join(", "),
+        tools: (full.tools || []).join(", "),
+        model: full.model || "",
       });
     } catch {
       setForm({
@@ -71,13 +73,15 @@ export function Playbook() {
         goal: playbookSummary.goal || "",
         instructions: playbookSummary.instructions || "",
         tags: (playbookSummary.tags || []).join(", "),
+        tools: (playbookSummary.tools || []).join(", "),
+        model: playbookSummary.model || "",
       });
     }
   };
 
   const resetForm = () => {
     setSelectedId(null);
-    setForm({ title: "", goal: "", instructions: "", tags: "" });
+    setForm({ title: "", goal: "", instructions: "", tags: "", tools: "", model: "" });
     setMessage("");
   };
 
@@ -91,6 +95,8 @@ export function Playbook() {
       goal: form.goal,
       instructions: form.instructions,
       tags: form.tags.split(",").map(t => t.trim()).filter(Boolean),
+      tools: (form.tools || "").split(",").map(t => t.trim()).filter(Boolean),
+      model: (form.model || "").trim(),
     };
     const isUpdate = Boolean(selectedId);
     const safeId = isUpdate ? encodeURIComponent(String(selectedId)) : null;
@@ -352,6 +358,20 @@ export function Playbook() {
               onChange={e => setForm(prev => ({ ...prev, tags: e.target.value }))}
               style={{ padding: "0.9rem", background: "#222", color: "#eee", border: "1px solid #333", borderRadius: "10px" }}
             />
+            <input
+              type="text"
+              placeholder="Tools (comma separated): search_memory, search_history, search_documents, list_models, get_time"
+              value={form.tools}
+              onChange={e => setForm(prev => ({ ...prev, tools: e.target.value }))}
+              style={{ padding: "0.9rem", background: "#222", color: "#eee", border: "1px solid #333", borderRadius: "10px" }}
+            />
+            <input
+              type="text"
+              placeholder="Model (blank = auto-select): e.g. mistral:latest"
+              value={form.model}
+              onChange={e => setForm(prev => ({ ...prev, model: e.target.value }))}
+              style={{ padding: "0.9rem", background: "#222", color: "#eee", border: "1px solid #333", borderRadius: "10px" }}
+            />
             <textarea
               rows={4}
               placeholder="Goal"
diff --git a/interface/web/src/Settings.jsx b/interface/web/src/Settings.jsx
index f51e802..94bc4c9 100644
--- a/interface/web/src/Settings.jsx
+++ b/interface/web/src/Settings.jsx
@@ -5,6 +5,7 @@ const DEFAULTS = {
   model: "",
   think: false, // Qwen3-style reasoning; off = much faster chat/memory
   temperature: 0.7,
+  num_ctx: 0, // context window in tokens; 0 = model default
   system_prompt: "",
   timeout: 120,
   gpu_offload: -1, // -1 = Auto; 0–100 = percent of layers forced onto the GPU
@@ -188,6 +189,26 @@ export function Settings() {
           </div>
         </div>
 
+        <div style={{ marginTop: "1.25rem" }}>
+          <label style={labelStyle}>
+            Context Window (num_ctx)
+            <span style={{ float: "right", color: "#7aa", fontWeight: 600, textTransform: "none", letterSpacing: 0 }}>
+              {form.num_ctx > 0 ? `${form.num_ctx} tok` : "Model default"}
+            </span>
+          </label>
+          <input
+            type="number"
+            min="0"
+            step="512"
+            value={form.num_ctx}
+            onChange={e => update("num_ctx", parseInt(e.target.value) || 0)}
+            style={{ width: "100%", padding: "0.6rem", background: "#222", color: "#eee", border: "1px solid #333", borderRadius: "8px", boxSizing: "border-box" }}
+          />
+          <div style={{ fontSize: "0.72rem", color: "#555", marginTop: "0.2rem" }}>
+            0 = use the model's default. Larger fits more context but uses more memory.
+          </div>
+        </div>
+
         <div style={{ marginTop: "1.25rem" }}>
           <label style={labelStyle}>
             GPU Offload
diff --git a/management/ncp.py b/management/ncp.py
index cad0df5..9f018f4 100644
--- a/management/ncp.py
+++ b/management/ncp.py
@@ -301,20 +301,23 @@ def stop_service(svc: Service) -> bool:
 
 # -- ollama --------------------------------------------------------------------
 
-def start_ollama() -> None:
+def start_ollama(background: bool = False) -> None:
     """Driven through the backend endpoint (the path the control panel uses)
     rather than launching the binary, because OllamaManager owns model and GPU
     selection. Requires the backend to be up.
 
-    Long timeout: the endpoint blocks until the model is warmed - weights read
-    off disk into RAM/VRAM - which the web UI's own "Loading model..." button
-    state calls out as routinely taking about a minute, not just the Ollama
-    process launching."""
+    background=True (`ncp start`): the endpoint returns as soon as `ollama serve`
+    is up and warms the model in a background task, so boot finishes in seconds
+    and the model loads concurrently into the first chat.
+    background=False (`ncp start --ai`): blocks until the model is warmed - weights
+    read off disk into RAM/VRAM, routinely about a minute - so "started" means the
+    AI can actually answer."""
     print("Starting OLLAMA...")
-    req = urllib.request.Request("http://localhost:8000/ollama/start", method="POST")
+    url = "http://localhost:8000/ollama/start" + ("?background=true" if background else "")
+    req = urllib.request.Request(url, method="POST")
     try:
         urllib.request.urlopen(req, timeout=180).read(1)
-        print("NEXUS OLLAMA STARTED")
+        print("NEXUS OLLAMA WARMING (background)" if background else "NEXUS OLLAMA STARTED")
     except Exception as e:
         print(f"  OLLAMA start failed: {e}")
 
@@ -350,14 +353,24 @@ def cmd_start(target) -> None:
     elif target in ("--ai", "-a"):
         start_ollama()
     elif target in (None, "", "all"):
-        # Memory + backend in parallel, both ready before the frontend starts.
+        # Bring the UI up first, then warm Ollama in the background — the model
+        # loads concurrently and into the first chat instead of blocking boot.
+        t0 = time.perf_counter()
         launch(SERVICES["memory"])
         launch(SERVICES["backend"])
         wait_for_port(SERVICES["memory"])
         wait_for_port(SERVICES["backend"])
-        start_ollama()
+        t_services = time.perf_counter()
         launch(SERVICES["frontend"])
         wait_for_port(SERVICES["frontend"])
+        t_frontend = time.perf_counter()
+        start_ollama(background=True)
+        t_ollama = time.perf_counter()
+        print("\nBoot timing:")
+        print(f"  services (memory+backend) : {t_services - t0:5.1f}s")
+        print(f"  frontend (UI ready)       : {t_frontend - t_services:5.1f}s")
+        print(f"  ollama kickoff (bg warm)  : {t_ollama - t_frontend:5.1f}s")
+        print(f"  total to interactive      : {t_ollama - t0:5.1f}s")
     else:
         show_help()
 
diff --git a/synapse/chat.py b/synapse/chat.py
index 843af1d..f14a241 100644
--- a/synapse/chat.py
+++ b/synapse/chat.py
@@ -8,6 +8,11 @@ from typing import AsyncGenerator, Dict, List, Optional, Any
 
 from .nexus_config import settings, DEFAULT_CHAT_MODEL
 from .ollama_manager import get_ollama_manager
+from . import tools as _tools
+
+# Cap on tool-call round-trips before the final answer — stops a confused small
+# model from looping forever.
+MAX_TOOL_STEPS = 5
 
 
 # -------------------------
@@ -126,6 +131,38 @@ async def _normalize_to_async_generator(maybe_iterable) -> AsyncGenerator[str, N
         yield str(item)
 
 
+async def _run_tool_loop(manager, messages, model, tool_schemas, temperature, num_gpu):
+    """Let the model call read-only tools before the final streamed answer.
+
+    Mutates `messages` IN PLACE, appending the assistant tool-call turns and
+    their `role:"tool"` results, and yields a `__status__<tool>` sentinel before
+    each tool runs (surfaced to the UI as a "running tool" indicator).
+    Non-streamed — tool calls arrive as whole messages. Degrades to an untouched
+    `messages` if the model can't do tool calling.
+
+    ponytail: the turn that finally returns content is thrown away and the answer
+    is re-generated by the streaming turn (one wasted call). Simpler than
+    streaming a maybe-already-complete message; revisit if latency matters.
+    """
+    for _ in range(MAX_TOOL_STEPS):
+        msg = await manager.chat(
+            messages=messages, model=model, stream=False,
+            temperature=temperature, num_gpu=num_gpu, tools=tool_schemas,
+        )
+        if not isinstance(msg, dict):
+            break  # None/error or no tool support -> fall back to plain stream
+        calls = msg.get("tool_calls")
+        if not calls:
+            break
+        messages.append(msg)
+        for c in calls:
+            fn = c.get("function", {})
+            name = fn.get("name", "")
+            yield f"__status__{name}"
+            result = await _tools.dispatch(name, fn.get("arguments"))
+            messages.append({"role": "tool", "content": result})
+
+
 # -------------------------
 # Streaming implementation
 # -------------------------
@@ -143,6 +180,7 @@ async def stream_chat_response(
     model = metadata.get("model") or DEFAULT_CHAT_MODEL
     temperature = metadata.get("temperature")
     num_gpu = metadata.get("num_gpu")
+    num_ctx = metadata.get("num_ctx")
     think = metadata.get("think", False)
 
     # Build messages array for /api/chat multi-turn format
@@ -151,7 +189,21 @@ async def stream_chat_response(
         messages.append({"role": "system", "content": system})
     for msg in (history or []):
         messages.append({"role": msg["role"], "content": msg["content"]})
-    messages.append({"role": "user", "content": user_message})
+    user_msg: Dict[str, Any] = {"role": "user", "content": user_message}
+    images = metadata.get("images")  # base64 strings (no data: prefix) for vision models
+    if images:
+        user_msg["images"] = images
+    messages.append(user_msg)
+
+    # Tool-using playbooks: run read-only tool calls, then stream the final answer
+    # with their results already in the messages array.
+    tool_schemas = metadata.get("tools")
+    if tool_schemas:
+        try:
+            async for status in _run_tool_loop(manager, messages, model, tool_schemas, temperature, num_gpu):
+                yield status
+        except Exception:
+            _logger.exception("tool loop failed; streaming without tools")
 
     _logger.info("stream_chat_response: starting stream (model=%s, turns=%d, timeout=%s)", model, len(messages), timeout)
 
@@ -162,7 +214,7 @@ async def stream_chat_response(
     _synapse_trace(f"USR: {user_message}\n{'─' * 50}\n")
 
     try:
-        maybe_iter = manager.chat(messages=messages, model=model, stream=True, temperature=temperature, num_gpu=num_gpu, think=think)
+        maybe_iter = manager.chat(messages=messages, model=model, stream=True, temperature=temperature, num_gpu=num_gpu, think=think, num_ctx=num_ctx)
         async_gen = _normalize_to_async_generator(maybe_iter)
 
         buffer_parts: list[str] = []
diff --git a/synapse/main.py b/synapse/main.py
index 7e714ce..60747b1 100644
--- a/synapse/main.py
+++ b/synapse/main.py
@@ -19,6 +19,7 @@ from .nexus_config import settings, VERSION, DEFAULT_CHAT_MODEL
 from .chat import generate_chat_response, stream_chat_response, _synapse_trace
 from .ollama_manager import initialize_ollama, initialize_ollama_async, get_ollama_manager
 from .playbook_manager import PlaybookManager
+from . import tools as _tools
 
 def _render_memory_block(facts) -> str:
     """Render memory items as grouped ## Section / - bullet markdown.
@@ -230,11 +231,15 @@ async def chat_stream_endpoint(payload: Dict[str, Any]):
     try:
         message = payload.get("message", "")
         app_settings = store.get_settings()
-        model = payload.get("model") or await _auto_select_model(message)
+        # Model precedence: explicit request > active playbook's pinned model > auto-select.
+        _active_pb = playbooks.get_main_playbook()
+        _pb_model = _active_pb.model if (_active_pb and _active_pb.model) else ""
+        model = payload.get("model") or _pb_model or await _auto_select_model(message)
         context = payload.get("context", {})
         conversation_id = payload.get("conversation_id") or str(_uuid.uuid4())
         history = payload.get("history", [])
         temperature = payload.get("temperature", app_settings.get("temperature"))
+        num_ctx = payload.get("num_ctx", app_settings.get("num_ctx", 0))
         think = payload.get("think", app_settings.get("think", False))
         gpu_offload = payload.get("gpu_offload", app_settings.get("gpu_offload", -1))
         num_gpu = await get_ollama_manager().resolve_num_gpu(gpu_offload, model)
@@ -280,6 +285,13 @@ async def chat_stream_endpoint(payload: Dict[str, Any]):
             separator = "\n\n---\nRelevant past exchanges (use as background context only):\n\n"
             system_prompt = (system_prompt + separator + memory_block) if system_prompt else memory_block
 
+        # Retrieve relevant uploaded documents (RAG) and inject the top chunks.
+        doc_hits = await store.search_documents(message, get_ollama_manager().embed, limit=3)
+        if doc_hits:
+            doc_block = "\n\n".join(f"[{d['title']}]\n{d['text']}" for d in doc_hits)
+            separator = "\n\n---\nRelevant documents (cite as source material):\n\n"
+            system_prompt = (system_prompt + separator + doc_block) if system_prompt else doc_block
+
         # Fetch web search results for time-sensitive queries
         search_results = ""
         if needs_web_search(message):
@@ -338,7 +350,19 @@ async def chat_stream_endpoint(payload: Dict[str, Any]):
         _synapse_trace(f"{'─' * 55}\n")
         # ── end MindTrace pre-flight ──────────────────────────────────────
 
-        metadata: Dict[str, Any] = {"model": model, "context": context, "system": system_prompt, "temperature": temperature, "num_gpu": num_gpu, "think": think}
+        metadata: Dict[str, Any] = {"model": model, "context": context, "system": system_prompt, "temperature": temperature, "num_gpu": num_gpu, "num_ctx": num_ctx, "think": think}
+
+        # Vision: base64 images (data: prefix stripped by the client) ride on the user turn.
+        images = payload.get("images")
+        if images:
+            metadata["images"] = images
+
+        # Tool-using playbook: advertise the active playbook's allowlisted tools.
+        if _main_pb and getattr(_main_pb, "tools", None):
+            schemas = _tools.schemas_for(_main_pb.tools)
+            if schemas:
+                metadata["tools"] = schemas
+                _synapse_trace(f"  TOOLS   : {', '.join(_main_pb.tools)}\n")
 
         # Persist conversation and user message before streaming
         store.create_conversation(conversation_id)
@@ -363,6 +387,9 @@ async def chat_stream_endpoint(payload: Dict[str, Any]):
                             pass
                         yield f"event: meta\ndata: {chunk[8:]}\n\n"
                         continue
+                    if chunk.startswith("__status__"):
+                        yield f"event: status\ndata: {_json.dumps({'tool': chunk[10:]})}\n\n"
+                        continue
                     response_chunks.append(chunk)
                     yield f"data: {_json.dumps(chunk)}\n\n"
             except _asyncio.TimeoutError:
@@ -637,13 +664,26 @@ async def ollama_status_endpoint():
 # -------------------------
 # Ollama Start
 # -------------------------
+_warm_tasks: set = set()
+
+
+async def _warm_default_model():
+    """Load the default model into RAM/VRAM so the first chat isn't a cold read.
+    Returns the model name. Raises are the caller's to swallow."""
+    s = store.get_settings()
+    warm_model = s.get("model") or await ollama.select_best_model()
+    num_gpu = await ollama.resolve_num_gpu(s.get("gpu_offload", -1), warm_model)
+    await ollama.warm(warm_model, num_gpu)
+    return warm_model
+
+
 @app.post("/ollama/start")
-async def ollama_start_endpoint():
+async def ollama_start_endpoint(background: bool = False):
     try:
         global ollama
         if ollama is None:
             ollama = initialize_ollama()
-        
+
         # start_async, NOT start: the sync one polls with time.sleep(1) up to 30
         # times, which blocks the event loop — the whole backend (including the
         # UI's 5s status poll) goes dead while Ollama boots, so a slow start
@@ -653,19 +693,24 @@ async def ollama_start_endpoint():
 
         is_running = ollama.is_running() if hasattr(ollama, "is_running") else True
 
-        # Warm the default model so the first chat isn't a cold load. This blocks
-        # until the model is resident, so the UI's Start finishes only once the AI
-        # is actually ready to answer. Best-effort — warm() never raises.
+        # Warm the default model so the first chat isn't a cold load.
+        #   background=False (UI "Start AI"): block until resident, so the button
+        #     finishes only once the AI can actually answer.
+        #   background=True (`ncp start`): fire-and-forget so boot returns fast and
+        #     the model warms concurrently — Ollama serialises the load, so a first
+        #     chat that arrives mid-warm simply waits on the same load.
         warmed = None
         if is_running:
-            try:
-                s = store.get_settings()
-                warm_model = s.get("model") or await ollama.select_best_model()
-                num_gpu = await ollama.resolve_num_gpu(s.get("gpu_offload", -1), warm_model)
-                await ollama.warm(warm_model, num_gpu)
-                warmed = warm_model
-            except Exception:
-                pass
+            if background:
+                task = _asyncio.create_task(_warm_default_model())
+                _warm_tasks.add(task)                       # hold a ref (asyncio only weak-refs tasks)
+                task.add_done_callback(_warm_tasks.discard)
+                warmed = "background"
+            else:
+                try:
+                    warmed = await _warm_default_model()
+                except Exception:
+                    pass
 
         return {"status": "started" if is_running else "failed", "running": is_running, "warmed": warmed}
     except Exception as e:
@@ -701,6 +746,8 @@ async def get_playbooks():
                     "goal": p.goal,
                     "instructions": getattr(p, "instructions", ""),
                     "tags": getattr(p, "tags", []),
+                    "tools": getattr(p, "tools", []),
+                    "model": getattr(p, "model", ""),
                 }
                 for p in playbook_list
             ]
@@ -749,11 +796,13 @@ def _persist_playbook(playbook_dict: Dict[str, Any]) -> Dict[str, Any]:
             goal=playbook_dict.get("goal", ""),
             instructions=playbook_dict.get("instructions", ""),
             tags=playbook_dict.get("tags", []),
+            tools=playbook_dict.get("tools", []),
+            model=playbook_dict.get("model", ""),
             order=order
         )
 
         playbook_store.add_playbook(playbook_item)
-        
+
         # Return as dict
         return {
             "id": playbook_item.id,
@@ -761,6 +810,8 @@ def _persist_playbook(playbook_dict: Dict[str, Any]) -> Dict[str, Any]:
             "goal": playbook_item.goal,
             "instructions": playbook_item.instructions,
             "tags": playbook_item.tags,
+            "tools": playbook_item.tools,
+            "model": playbook_item.model,
         }
     except Exception as e:
         raise HTTPException(status_code=500, detail=f"Failed to persist playbook: {str(e)}")
@@ -810,6 +861,8 @@ async def get_playbook(id: UUID):
             "goal": getattr(pb, "goal", None) or (pb.get("goal") if isinstance(pb, dict) else None),
             "instructions": getattr(pb, "instructions", "") or (pb.get("instructions") if isinstance(pb, dict) else ""),
             "tags": getattr(pb, "tags", []) or (pb.get("tags") if isinstance(pb, dict) else []),
+            "tools": getattr(pb, "tools", []) or (pb.get("tools") if isinstance(pb, dict) else []),
+            "model": getattr(pb, "model", "") or (pb.get("model") if isinstance(pb, dict) else ""),
         }
         return result
     except HTTPException:
@@ -880,6 +933,41 @@ async def delete_playbook_endpoint(id: UUID):
         raise HTTPException(status_code=500, detail=str(e))
 
 
+# -------------------------
+# Documents (RAG)
+# -------------------------
+@app.get("/documents")
+async def list_documents():
+    return {"documents": store.list_documents()}
+
+
+@app.post("/documents")
+async def add_document(payload: Dict[str, Any] = Body(...)):
+    title = (payload.get("title") or "").strip()
+    content = (payload.get("content") or "").strip()
+    if not title or not content:
+        raise HTTPException(status_code=400, detail="title and content are required")
+    result = await store.add_document(title, content, get_ollama_manager().embed)
+    if result["chunks"] == 0:
+        raise HTTPException(status_code=400, detail="no text to index")
+    return result
+
+
+@app.get("/documents/{doc_id}")
+async def get_document(doc_id: str):
+    chunks = store.get_document(doc_id)
+    if not chunks:
+        raise HTTPException(status_code=404, detail="Not Found")
+    return {"doc_id": doc_id, "chunks": chunks}
+
+
+@app.delete("/documents/{doc_id}")
+async def delete_document(doc_id: str):
+    if not store.delete_document(doc_id):
+        raise HTTPException(status_code=404, detail="Not Found")
+    return {"status": "deleted"}
+
+
 # -------------------------
 # Unified Search
 # -------------------------
@@ -914,19 +1002,24 @@ async def get_conversations(q: Optional[str] = None):
 
 
 @app.get("/conversations/export")
-async def export_conversations(min_turns: int = 1):
+async def export_conversations(min_turns: int = 1, conversation_id: Optional[str] = None):
     """Export conversations as ShareGPT JSONL for fine-tuning.
 
     Each line is one conversation:
       {"conversations": [{"from": "human", "value": "..."}, {"from": "gpt", "value": "..."}]}
 
     Query params:
-      min_turns  — minimum user/assistant exchanges to include (default 1)
+      min_turns        — minimum user/assistant exchanges to include (default 1)
+      conversation_id  — export just this one conversation (default: all)
     """
     from fastapi.responses import Response
     import datetime
 
-    conversations = store.all_conversations()
+    if conversation_id:
+        one = store.get_conversation(conversation_id)
+        conversations = [one] if one else []
+    else:
+        conversations = store.all_conversations()
     lines = []
 
     for conv in conversations:
diff --git a/synapse/memory/store.py b/synapse/memory/store.py
index ce48ea5..37f4692 100644
--- a/synapse/memory/store.py
+++ b/synapse/memory/store.py
@@ -150,6 +150,22 @@ class PersistentMemoryStore:
             )
         """)
 
+        # RAG: one row per chunk. doc_id groups the chunks of a single uploaded
+        # document; embedding is a JSON vector (search_document-prefixed), set at
+        # ingest so retrieval needs no backfill.
+        cur.execute("""
+            CREATE TABLE IF NOT EXISTS documents (
+                id TEXT PRIMARY KEY,
+                doc_id TEXT NOT NULL,
+                title TEXT NOT NULL,
+                chunk_idx INTEGER NOT NULL,
+                text TEXT NOT NULL,
+                embedding TEXT,
+                created_at REAL NOT NULL
+            )
+        """)
+        cur.execute("CREATE INDEX IF NOT EXISTS idx_documents_doc_id ON documents (doc_id)")
+
         cur.execute("""
             CREATE TABLE IF NOT EXISTS settings (
                 key TEXT PRIMARY KEY,
@@ -602,6 +618,106 @@ class PersistentMemoryStore:
             "matches": matches,
         }
 
+    # -----------------------------
+    # Documents (RAG)
+    # -----------------------------
+    @staticmethod
+    def _chunk_text(text: str, size: int = 800) -> List[str]:
+        """Split on blank lines, then pack paragraphs into ~`size`-char chunks.
+        ponytail: naive char-based packing, no token counting or overlap — good
+        enough for local recall; add overlap if retrieval misses boundaries."""
+        chunks: List[str] = []
+        buf = ""
+        for para in (p.strip() for p in text.split("\n\n")):
+            if not para:
+                continue
+            if buf and len(buf) + len(para) + 2 > size:
+                chunks.append(buf)
+                buf = para
+            else:
+                buf = f"{buf}\n\n{para}" if buf else para
+        if buf:
+            chunks.append(buf)
+        return chunks
+
+    async def add_document(self, title: str, content: str, embed_fn) -> dict:
+        """Chunk, embed, and store a document. Returns {doc_id, chunks}."""
+        import uuid as _uuid
+        doc_id = str(_uuid.uuid4())
+        pieces = self._chunk_text(content)
+        now = time.time()
+        conn = self._connect()
+        cur = conn.cursor()
+        for i, piece in enumerate(pieces):
+            vec = await embed_fn(self._EMBED_DOC_PREFIX + piece[:2000])
+            cur.execute(
+                "INSERT INTO documents (id, doc_id, title, chunk_idx, text, embedding, created_at)"
+                " VALUES (?, ?, ?, ?, ?, ?, ?)",
+                (str(_uuid.uuid4()), doc_id, title, i, piece,
+                 json.dumps(vec) if vec else None, now),
+            )
+        conn.commit()
+        conn.close()
+        return {"doc_id": doc_id, "title": title, "chunks": len(pieces)}
+
+    def list_documents(self) -> List[dict]:
+        conn = self._connect()
+        cur = conn.cursor()
+        cur.execute("""
+            SELECT doc_id, title, COUNT(*) AS chunks, MIN(created_at) AS created_at
+            FROM documents GROUP BY doc_id, title ORDER BY created_at DESC
+        """)
+        rows = cur.fetchall()
+        conn.close()
+        return [dict(r) for r in rows]
+
+    def get_document(self, doc_id: str) -> List[dict]:
+        """Ordered chunks of one document: [{chunk_idx, text}]."""
+        conn = self._connect()
+        cur = conn.cursor()
+        cur.execute(
+            "SELECT chunk_idx, text FROM documents WHERE doc_id = ? ORDER BY chunk_idx",
+            (doc_id,),
+        )
+        rows = cur.fetchall()
+        conn.close()
+        return [dict(r) for r in rows]
+
+    def delete_document(self, doc_id: str) -> bool:
+        conn = self._connect()
+        cur = conn.cursor()
+        cur.execute("DELETE FROM documents WHERE doc_id = ?", (doc_id,))
+        deleted = cur.rowcount
+        conn.commit()
+        conn.close()
+        return deleted > 0
+
+    async def search_documents(
+        self, query: str, embed_fn, limit: int = 3, min_score: float = 0.6
+    ) -> List[dict]:
+        """Top-`limit` document chunks most similar to `query`. Returns
+        [{title, text, score}]. Empty on no query / embeddings down."""
+        if not query or not query.strip():
+            return []
+        query_vec = await embed_fn(self._EMBED_QUERY_PREFIX + query.strip())
+        if not query_vec:
+            return []
+        conn = self._connect()
+        cur = conn.cursor()
+        cur.execute("SELECT title, text, embedding FROM documents WHERE embedding IS NOT NULL")
+        scored = []
+        for row in cur.fetchall():
+            try:
+                vec = json.loads(row["embedding"])
+            except Exception:
+                continue
+            score = _cosine(query_vec, vec)
+            if score >= min_score:
+                scored.append({"title": row["title"], "text": row["text"], "score": score})
+        conn.close()
+        scored.sort(key=lambda d: d["score"], reverse=True)
+        return scored[:limit]
+
     # -----------------------------
     # Settings API
     # -----------------------------
@@ -611,6 +727,8 @@ class PersistentMemoryStore:
         # latency for chat/memory. Turn on for hard multi-step problems.
         "think": False,
         "temperature": 0.7,
+        # Context window (tokens Ollama keeps in view). 0 → Ollama's model default.
+        "num_ctx": 0,
         "system_prompt": "",
         "timeout": 120,
         # How long Ollama keeps the model resident in VRAM between messages.
diff --git a/synapse/ollama_manager.py b/synapse/ollama_manager.py
index 27bfdbd..3c897bd 100644
--- a/synapse/ollama_manager.py
+++ b/synapse/ollama_manager.py
@@ -175,7 +175,7 @@ def _preferred_model(models: list, preference) -> str | None:
     return None
 
 
-def _chat_options(temperature: float | None, num_gpu: int | None) -> dict:
+def _chat_options(temperature: float | None, num_gpu: int | None, num_ctx: int | None = None) -> dict:
     """Assemble the Ollama `options` block from the knobs we expose.
 
     Returns an empty dict when nothing is set so callers can omit `options`
@@ -186,6 +186,8 @@ def _chat_options(temperature: float | None, num_gpu: int | None) -> dict:
         opts["temperature"] = temperature
     if num_gpu is not None:
         opts["num_gpu"] = num_gpu
+    if num_ctx:  # 0 / None -> let Ollama use the model default
+        opts["num_ctx"] = num_ctx
     return opts
 
 
@@ -503,10 +505,16 @@ class OllamaManager:
         temperature: float | None = None,
         num_gpu: int | None = None,
         think: bool = False,
+        tools: list | None = None,
+        num_ctx: int | None = None,
         **kwargs,
     ):
         """Multi-turn chat via /api/chat (accepts a messages array with roles).
 
+        When `tools` is given (non-stream only), the request advertises them and
+        the FULL message dict is returned (so the caller sees `tool_calls`);
+        otherwise the response content string is returned as before.
+
         `think` toggles Qwen3-style reasoning. Default off: the hidden <think>
         block is pure latency for chat/memory. Ollama ignores it for models that
         don't support thinking.
@@ -516,12 +524,14 @@ class OllamaManager:
             if stream:
                 return self._chat_stream(
                     messages=messages, model=model, temperature=temperature,
-                    num_gpu=num_gpu, think=think, start=start,
+                    num_gpu=num_gpu, think=think, start=start, num_ctx=num_ctx,
                 )
             else:
                 body: dict = {"model": model, "messages": messages, "stream": False}
                 body["think"] = think
-                opts = _chat_options(temperature, num_gpu)
+                if tools:
+                    body["tools"] = tools
+                opts = _chat_options(temperature, num_gpu, num_ctx)
                 if opts:
                     body["options"] = opts
                 self._apply_keep_alive(body)
@@ -529,7 +539,9 @@ class OllamaManager:
                     r = await client.post(f"{self._api_base}/api/chat", json=body)
                 elapsed = time.perf_counter() - start
                 r.raise_for_status()
-                return r.json().get("message", {}).get("content", "")
+                message = r.json().get("message", {})
+                # Tool callers need the whole message (tool_calls); others want content.
+                return message if tools else message.get("content", "")
         except Exception as e:
             elapsed = time.perf_counter() - start
             _log.exception("chat error after %.3fs: %s", elapsed, e)
@@ -643,12 +655,12 @@ class OllamaManager:
 
     async def _chat_stream(self, messages: list, model: str, start: float,
                            temperature: float | None = None, num_gpu: int | None = None,
-                           think: bool = False):
+                           think: bool = False, num_ctx: int | None = None):
         """Async generator streaming tokens, then a final __meta__ stats sentinel."""
         try:
             body: dict = {"model": model, "messages": messages, "stream": True}
             body["think"] = think  # see chat(): reasoning off by default for speed
-            opts = _chat_options(temperature, num_gpu)
+            opts = _chat_options(temperature, num_gpu, num_ctx)
             if opts:
                 body["options"] = opts
             self._apply_keep_alive(body)
diff --git a/synapse/playbooks/store.py b/synapse/playbooks/store.py
index c5fea4b..ce7aca6 100644
--- a/synapse/playbooks/store.py
+++ b/synapse/playbooks/store.py
@@ -22,6 +22,8 @@ class PlaybookItem(BaseModel):
     goal: str
     instructions: str
     tags: List[str] = []
+    tools: List[str] = []
+    model: str = ""
     order: int = 0
 
 
@@ -43,6 +45,8 @@ class PlaybookFileStore:
                 goal=data.get("goal", ""),
                 instructions=data.get("instructions", ""),
                 tags=data.get("tags", []),
+                tools=data.get("tools", []),
+                model=data.get("model", ""),
                 order=data.get("order", 0),
             )
         except Exception:
@@ -58,6 +62,8 @@ class PlaybookFileStore:
             "title": item.title,
             "goal": item.goal,
             "tags": item.tags,
+            "tools": item.tools,
+            "model": item.model,
             "order": item.order,
             "instructions": self._clean(item.instructions),
         }
diff --git a/synapse/tools.py b/synapse/tools.py
new file mode 100644
index 0000000..68d26b5
--- /dev/null
+++ b/synapse/tools.py
@@ -0,0 +1,138 @@
+"""Read-only tools a playbook can call during chat.
+
+Ollama drives the calling: `/api/chat` with a `tools` param returns
+`message.tool_calls`, and this module is just the registry + dispatch. Every
+tool here only READS local state (SQLite, Ollama) — no side effects. The
+per-playbook allowlist (`PlaybookItem.tools`) is the security boundary; keep the
+registry read-only until the loop is trusted.
+"""
+from __future__ import annotations
+
+import json
+from typing import Awaitable, Callable
+
+from .memory.store import store
+from .ollama_manager import get_ollama_manager
+
+
+async def _search_memory(query: str = "", **_) -> str:
+    q = (query or "").strip().lower()
+    hits = [
+        {"section": it.section, "text": it.text}
+        for it in store.all()
+        if not q
+        or q in it.text.lower()
+        or q in (it.section or "").lower()
+        or any(q in t.lower() for t in it.tags)
+    ]
+    return json.dumps(hits[:20])
+
+
+async def _search_history(query: str = "", **_) -> str:
+    # Hybrid recall: semantic (embeddings) unioned with lexical, falls back to
+    # lexical if embeddings are down. Same retrieval the chat endpoint uses.
+    convs = await store.semantic_search_conversations(
+        query or "", get_ollama_manager().embed, limit=3
+    )
+    return json.dumps([{"matches": c.get("matches", [])} for c in convs])
+
+
+async def _list_models(**_) -> str:
+    return json.dumps(await get_ollama_manager().list_models())
+
+
+async def _search_documents(query: str = "", **_) -> str:
+    hits = await store.search_documents(query or "", get_ollama_manager().embed, limit=3)
+    return json.dumps([{"title": h["title"], "text": h["text"]} for h in hits])
+
+
+async def _get_time(**_) -> str:
+    from datetime import datetime
+    return json.dumps({"now": datetime.now().isoformat(timespec="seconds")})
+
+
+# name -> (schema, callable). Schema is the OpenAI/Ollama function-tool format.
+REGISTRY: dict[str, tuple[dict, Callable[..., Awaitable[str]]]] = {
+    "search_memory": (
+        {
+            "type": "function",
+            "function": {
+                "name": "search_memory",
+                "description": "Search the user's persistent memory facts. Empty query returns all facts.",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"query": {"type": "string", "description": "text to match"}},
+                },
+            },
+        },
+        _search_memory,
+    ),
+    "search_history": (
+        {
+            "type": "function",
+            "function": {
+                "name": "search_history",
+                "description": "Search past conversations for exchanges containing the query text.",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"query": {"type": "string"}},
+                    "required": ["query"],
+                },
+            },
+        },
+        _search_history,
+    ),
+    "list_models": (
+        {
+            "type": "function",
+            "function": {
+                "name": "list_models",
+                "description": "List the locally installed Ollama models.",
+                "parameters": {"type": "object", "properties": {}},
+            },
+        },
+        _list_models,
+    ),
+    "search_documents": (
+        {
+            "type": "function",
+            "function": {
+                "name": "search_documents",
+                "description": "Search the user's uploaded documents for relevant passages.",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"query": {"type": "string"}},
+                    "required": ["query"],
+                },
+            },
+        },
+        _search_documents,
+    ),
+    "get_time": (
+        {
+            "type": "function",
+            "function": {
+                "name": "get_time",
+                "description": "Get the current local date and time.",
+                "parameters": {"type": "object", "properties": {}},
+            },
+        },
+        _get_time,
+    ),
+}
+
+
+def schemas_for(names: list[str]) -> list[dict]:
+    """Tool schemas for a playbook's allowlist; unknown names are dropped."""
+    return [REGISTRY[n][0] for n in (names or []) if n in REGISTRY]
+
+
+async def dispatch(name: str, args: dict | None) -> str:
+    """Run a tool by name. Never raises — returns an error string on failure."""
+    entry = REGISTRY.get(name)
+    if not entry:
+        return json.dumps({"error": f"unknown tool: {name}"})
+    try:
+        return await entry[1](**(args or {}))
+    except Exception as e:  # a broken tool must not kill the chat loop
+        return json.dumps({"error": f"{name} failed: {e}"})
diff --git a/tests/test_documents.py b/tests/test_documents.py
new file mode 100644
index 0000000..a1c3a95
--- /dev/null
+++ b/tests/test_documents.py
@@ -0,0 +1,57 @@
+"""Document ingest / RAG store — hermetic (fake embeddings, temp DB)."""
+import asyncio
+import tempfile
+from pathlib import Path
+
+from synapse.memory.store import PersistentMemoryStore
+
+
+def _store():
+    return PersistentMemoryStore(Path(tempfile.mkdtemp()) / "t.db")
+
+
+def test_chunker_packs_and_splits():
+    s = _store()
+    one = s._chunk_text("short one.\n\nshort two.")
+    assert one == ["short one.\n\nshort two."]  # both fit one chunk
+    many = s._chunk_text("a" * 700 + "\n\n" + "b" * 700)
+    assert len(many) == 2  # each paragraph near the size cap -> own chunk
+
+
+async def _fake_embed(text):
+    kws = ["lego", "star", "wars", "gpu", "vega"]
+    v = [float(text.lower().count(k)) for k in kws]
+    return v if any(v) else None
+
+
+def test_add_list_search_delete_roundtrip():
+    async def run():
+        s = _store()
+        r = await s.add_document(
+            "Guide",
+            "Beat the lego star wars boss with the force.\n\nUnrelated gpu vega notes.",
+            _fake_embed,
+        )
+        assert r["chunks"] >= 1
+        assert [d["title"] for d in s.list_documents()] == ["Guide"]
+
+        hits = await s.search_documents("lego star wars", _fake_embed, limit=2, min_score=0.1)
+        assert hits and "lego" in hits[0]["text"].lower()
+        # scores are sorted descending
+        assert all(hits[i]["score"] >= hits[i + 1]["score"] for i in range(len(hits) - 1))
+
+        # get_document returns ordered chunks for the viewer
+        chunks = s.get_document(r["doc_id"])
+        assert [c["chunk_idx"] for c in chunks] == list(range(len(chunks)))
+
+        assert s.delete_document(r["doc_id"]) is True
+        assert s.list_documents() == []
+        assert s.get_document(r["doc_id"]) == []       # gone -> no chunks
+        assert s.delete_document(r["doc_id"]) is False  # already gone
+
+    asyncio.run(run())
+
+
+def test_search_empty_query_returns_nothing():
+    s = _store()
+    assert asyncio.run(s.search_documents("", _fake_embed)) == []
diff --git a/tests/test_smoke.py b/tests/test_smoke.py
index 7cf0e8d..c6ba377 100644
--- a/tests/test_smoke.py
+++ b/tests/test_smoke.py
@@ -43,6 +43,14 @@ def test_keep_alive_pins_the_model():
     assert "keep_alive" not in mgr._apply_keep_alive({"model": "x"})
 
 
+def test_num_ctx_option_only_when_positive():
+    # 0 / None -> omit num_ctx so Ollama uses the model default; positive -> set it.
+    from synapse.ollama_manager import _chat_options
+    assert "num_ctx" not in _chat_options(None, None, 0)
+    assert "num_ctx" not in _chat_options(None, None, None)
+    assert _chat_options(None, None, 8192)["num_ctx"] == 8192
+
+
 def test_default_models_have_one_source_of_truth():
     # The curator default is the config constant, not a copy of it.
     assert PersistentMemoryStore._SETTINGS_DEFAULTS["memory_model"] == DEFAULT_MEMORY_MODEL
diff --git a/tests/test_tools.py b/tests/test_tools.py
new file mode 100644
index 0000000..1529ed2
--- /dev/null
+++ b/tests/test_tools.py
@@ -0,0 +1,74 @@
+"""Tool-using playbook loop — the read-only MVP.
+
+Run from nexus-core/ with the Promethean venv active:  pytest -q
+
+Hermetic: a fake manager stands in for Ollama, so no network/model is needed.
+Guards the two pieces that would silently break the feature: the allowlist
+filter and the tool-call loop's terminate-on-content behaviour.
+"""
+import asyncio
+
+from synapse import tools
+from synapse.chat import _run_tool_loop
+
+
+def test_schemas_for_drops_unknown_names():
+    schemas = tools.schemas_for(["search_memory", "not_a_tool"])
+    names = [s["function"]["name"] for s in schemas]
+    assert names == ["search_memory"]
+    assert tools.schemas_for([]) == []
+
+
+async def _drain(gen):
+    return [s async for s in gen]
+
+
+class _FakeManager:
+    """Returns a tool_call on the first chat() call, plain content after."""
+    def __init__(self):
+        self.calls = 0
+
+    async def chat(self, **_):
+        self.calls += 1
+        if self.calls == 1:
+            return {
+                "role": "assistant",
+                "tool_calls": [
+                    {"function": {"name": "search_memory", "arguments": {"query": "gpu"}}}
+                ],
+            }
+        return {"role": "assistant", "content": "here is the answer"}
+
+
+def test_tool_loop_runs_tool_then_stops(monkeypatch):
+    async def fake_dispatch(name, args):
+        assert name == "search_memory"
+        assert args == {"query": "gpu"}
+        return '[{"section": "GPU", "text": "Vega 20 4GB"}]'
+
+    monkeypatch.setattr(tools, "dispatch", fake_dispatch)
+
+    messages = [{"role": "user", "content": "what gpu do i have?"}]
+    schemas = tools.schemas_for(["search_memory"])
+    statuses = asyncio.run(_drain(
+        _run_tool_loop(_FakeManager(), messages, "m", schemas, None, None)
+    ))
+
+    # one status sentinel per tool run
+    assert statuses == ["__status__search_memory"]
+    # messages mutated in place: user -> assistant(tool_calls) -> tool(result);
+    # the final content turn is NOT appended (the streaming turn regenerates it).
+    assert [m["role"] for m in messages] == ["user", "assistant", "tool"]
+    assert "Vega 20" in messages[-1]["content"]
+
+
+def test_tool_loop_degrades_when_model_returns_no_dict():
+    class _NoToolManager:
+        async def chat(self, **_):
+            return None  # model can't do tools / errored
+
+    messages = [{"role": "user", "content": "hi"}]
+    before = list(messages)
+    statuses = asyncio.run(_drain(_run_tool_loop(_NoToolManager(), messages, "m", [{}], None, None)))
+    assert statuses == []          # no tool ran
+    assert messages == before      # untouched -> falls back to a plain stream