diff --git a/src/app/api/files/upload/route.ts b/src/app/api/files/upload/route.ts
index f93adff..2aa682d 100644
--- a/src/app/api/files/upload/route.ts
+++ b/src/app/api/files/upload/route.ts
@@ -9,6 +9,36 @@ import { resolveStateDir } from "@/lib/clawdbot/paths";
 export const runtime = "nodejs";
 
 const MAX_UPLOAD_BYTES = 10 * 1024 * 1024;
+const CONTENT_TYPE_BY_EXT: Record<string, string> = {
+  ".png": "image/png",
+  ".jpg": "image/jpeg",
+  ".jpeg": "image/jpeg",
+  ".gif": "image/gif",
+  ".webp": "image/webp",
+  ".txt": "text/plain",
+  ".md": "text/markdown",
+  ".markdown": "text/markdown",
+  ".csv": "text/csv",
+  ".json": "application/json",
+  ".xml": "application/xml",
+  ".pdf": "application/pdf",
+  ".js": "text/plain",
+  ".jsx": "text/plain",
+  ".ts": "text/plain",
+  ".tsx": "text/plain",
+  ".py": "text/plain",
+  ".rb": "text/plain",
+  ".go": "text/plain",
+  ".rs": "text/plain",
+  ".java": "text/plain",
+  ".kt": "text/plain",
+  ".sql": "text/plain",
+  ".html": "text/plain",
+  ".css": "text/plain",
+  ".yaml": "text/plain",
+  ".yml": "text/plain",
+  ".log": "text/plain",
+};
 const ALLOWED_CONTENT_TYPES = new Set([
   "image/png",
   "image/jpeg",
@@ -22,6 +52,7 @@ const ALLOWED_CONTENT_TYPES = new Set([
   "text/xml",
   "application/pdf",
 ]);
+const ALLOWED_EXTENSIONS = new Set(Object.keys(CONTENT_TYPE_BY_EXT));
 
 const TEXT_CONTENT_TYPES = [
   "text/",
@@ -39,6 +70,18 @@ const uploadsDir = () => path.join(resolveStateDir(), "claw3d", "uploads");
 const isTextContentType = (contentType: string): boolean =>
   TEXT_CONTENT_TYPES.some((prefix) => contentType.startsWith(prefix));
 
+const resolveUploadContentType = (file: File): string | null => {
+  const explicit = file.type.trim().toLowerCase();
+  if (explicit && (ALLOWED_CONTENT_TYPES.has(explicit) || explicit.startsWith("text/"))) {
+    return explicit;
+  }
+  const ext = path.extname(file.name || "").trim().toLowerCase();
+  if (!ext || !ALLOWED_EXTENSIONS.has(ext)) {
+    return null;
+  }
+  return CONTENT_TYPE_BY_EXT[ext] ?? null;
+};
+
 export async function POST(request: Request) {
   try {
     const formData = await request.formData();
@@ -53,9 +96,13 @@ export async function POST(request: Request) {
       return NextResponse.json({ error: "File exceeds 10 MB limit." }, { status: 400 });
     }
 
-    const contentType = file.type.trim().toLowerCase();
-    if (!contentType || !ALLOWED_CONTENT_TYPES.has(contentType) && !contentType.startsWith("text/")) {
-      return NextResponse.json({ error: `Unsupported file type: ${contentType || "(unknown)"}` }, { status: 400 });
+    const contentType = resolveUploadContentType(file);
+    if (!contentType) {
+      const ext = path.extname(file.name || "").trim().toLowerCase();
+      return NextResponse.json(
+        { error: `Unsupported file type: ${ext || file.type.trim().toLowerCase() || "(unknown)"}` },
+        { status: 400 }
+      );
     }
 
     const fileId = crypto.randomBytes(8).toString("hex");
diff --git a/src/features/agents/components/AgentChatPanel.tsx b/src/features/agents/components/AgentChatPanel.tsx
index a6c1fa6..4a2f34f 100644
--- a/src/features/agents/components/AgentChatPanel.tsx
+++ b/src/features/agents/components/AgentChatPanel.tsx
@@ -25,6 +25,7 @@ import type {
   ExecApprovalDecision,
   PendingExecApproval,
 } from "@/features/agents/approvals/types";
+import type { RuntimeAttachment } from "@/lib/runtime/types";
 import {
   buildAgentChatRenderBlocks,
   buildFinalAgentChatItems,
@@ -203,7 +204,7 @@ type AgentChatPanelProps = {
   onToolCallingToggle?: (enabled: boolean) => void;
   onThinkingTracesToggle?: (enabled: boolean) => void;
   onDraftChange: (value: string) => void;
-  onSend: (message: string) => void;
+  onSend: (message: string, attachments: RuntimeAttachment[]) => void;
   onRemoveQueuedMessage?: (index: number) => void;
   onStopRun: () => void;
   onAvatarShuffle: () => void;
@@ -1456,16 +1457,15 @@ export const AgentChatPanel = ({
     (message: string) => {
       if (!canSend) return;
       const trimmed = message.trim();
-      const attachmentBlocks = attachments.map(buildUploadedAttachmentPromptBlock);
-      const finalMessage = [trimmed, ...attachmentBlocks].filter(Boolean).join("\n\n").trim();
-      if (!finalMessage) return;
+      if (!trimmed && attachments.length === 0) return;
+      const pendingAttachments = attachments.map(({ id: _id, ...rest }) => rest as RuntimeAttachment);
       plainDraftRef.current = "";
       setDraftValue("");
       setAttachments([]);
       setAttachmentStatus(null);
       onDraftChange("");
       scrollToBottomNextOutputRef.current = true;
-      onSend(finalMessage);
+      onSend(trimmed, pendingAttachments);
     },
     [attachments, canSend, onDraftChange, onSend]
   );
diff --git a/src/features/agents/operations/chatSendOperation.ts b/src/features/agents/operations/chatSendOperation.ts
index 31675f5..64897bc 100644
--- a/src/features/agents/operations/chatSendOperation.ts
+++ b/src/features/agents/operations/chatSendOperation.ts
@@ -11,6 +11,7 @@ import {
 import type { AgentState } from "@/features/agents/state/store";
 import { randomUUID } from "@/lib/uuid";
 import type { TranscriptAppendMeta } from "@/features/agents/state/transcript";
+import type { RuntimeAttachment } from "@/lib/runtime/types";
 
 type SendDispatchAction =
   | { type: "updateAgent"; agentId: string; patch: Partial<AgentState> }
@@ -86,13 +87,15 @@ export async function sendChatMessageViaStudio(params: {
   agentId: string;
   sessionKey: string;
   message: string;
+  attachments?: RuntimeAttachment[];
   clearRunTracking?: (runId: string) => void;
   echoUserMessage?: boolean;
   now?: () => number;
   generateRunId?: () => string;
 }): Promise<void> {
   const trimmed = params.message.trim();
-  if (!trimmed) return;
+  const attachments = params.attachments ?? [];
+  if (!trimmed && attachments.length === 0) return;
   const echoUserMessage = params.echoUserMessage !== false;
 
   const generateRunId = params.generateRunId ?? (() => randomUUID());
@@ -206,6 +209,7 @@ export async function sendChatMessageViaStudio(params: {
     const sendResult = await params.client.call("chat.send", {
       sessionKey: params.sessionKey,
       message: buildAgentInstruction({ message: trimmed }),
+      ...(attachments.length > 0 ? { attachments } : {}),
       deliver: false,
       idempotencyKey: runId,
     });
diff --git a/src/features/agents/operations/useChatInteractionController.ts b/src/features/agents/operations/useChatInteractionController.ts
index c692e0e..8348e33 100644
--- a/src/features/agents/operations/useChatInteractionController.ts
+++ b/src/features/agents/operations/useChatInteractionController.ts
@@ -1,6 +1,7 @@
 import { useCallback, useEffect, useRef, useState } from "react";
 
 import { createRafBatcher } from "@/lib/dom";
+import type { RuntimeAttachment } from "@/lib/runtime/types";
 import {
   planDraftFlushIntent,
   planDraftTimerIntent,
@@ -23,6 +24,23 @@ type GatewayClientLike = {
   call: (method: string, params: unknown) => Promise<unknown>;
 };
 
+const buildQueuedAttachmentMessage = (message: string, attachments: RuntimeAttachment[]): string => {
+  const trimmed = message.trim();
+  const attachmentBlocks = attachments.map((attachment) => {
+    const lines = [
+      `[Attached file: ${attachment.name}]`,
+      `URL: ${attachment.url}`,
+      `Content-Type: ${attachment.contentType}`,
+    ];
+    if (attachment.extractedText?.trim()) {
+      lines.push("", attachment.extractedText.trim());
+    }
+    lines.push(`[End attached file: ${attachment.name}]`);
+    return lines.join("\n");
+  });
+  return [trimmed, ...attachmentBlocks].filter(Boolean).join("\n\n").trim();
+};
+
 export type UseChatInteractionControllerParams = {
   client: GatewayClientLike;
   status: GatewayStatus;
@@ -43,7 +61,7 @@ export type ChatInteractionController = {
   stopBusyAgentId: string | null;
   flushPendingDraft: (agentId: string | null) => void;
   handleDraftChange: (agentId: string, value: string) => void;
-  handleSend: (agentId: string, sessionKey: string, message: string) => Promise<void>;
+  handleSend: (agentId: string, sessionKey: string, message: string, attachments?: RuntimeAttachment[]) => Promise<void>;
   removeQueuedMessage: (agentId: string, index: number) => void;
   handleNewSession: (agentId: string) => Promise<void>;
   handleStopRun: (agentId: string, sessionKey: string) => Promise<void>;
@@ -186,9 +204,11 @@ export function useChatInteractionController(
   );
 
   const handleSend = useCallback(
-    async (agentId: string, sessionKey: string, message: string) => {
+    async (agentId: string, sessionKey: string, message: string, attachments?: RuntimeAttachment[]) => {
       const trimmed = message.trim();
-      if (!trimmed) return;
+      const normalizedAttachments = attachments ?? [];
+      const hasAttachments = normalizedAttachments.length > 0;
+      if (!trimmed && !hasAttachments) return;
       const pendingDraftTimer = pendingDraftTimersRef.current.get(agentId) ?? null;
       if (pendingDraftTimer !== null) {
         window.clearTimeout(pendingDraftTimer);
@@ -211,7 +231,7 @@ export function useChatInteractionController(
         params.dispatch({
           type: "enqueueQueuedMessage",
           agentId,
-          message: trimmed,
+          message: buildQueuedAttachmentMessage(trimmed, normalizedAttachments),
         });
         return;
       }
@@ -224,6 +244,7 @@ export function useChatInteractionController(
         agentId,
         sessionKey,
         message: trimmed,
+        attachments: normalizedAttachments,
         clearRunTracking: (runId) => params.clearRunTracking(runId),
       });
     },
diff --git a/src/features/agents/screens/AgentsPageScreen.tsx b/src/features/agents/screens/AgentsPageScreen.tsx
index 394aa32..2995969 100644
--- a/src/features/agents/screens/AgentsPageScreen.tsx
+++ b/src/features/agents/screens/AgentsPageScreen.tsx
@@ -864,9 +864,9 @@ const AgentsPageScreen = () => {
     });
   });
   const handleChatSend = useCallback(
-    async (agentId: string, sessionKey: string, message: string) => {
+    async (agentId: string, sessionKey: string, message: string, attachments?: import("@/lib/runtime/types").RuntimeAttachment[]) => {
       stopVoiceReplyPlayback();
-      await handleSend(agentId, sessionKey, message);
+      await handleSend(agentId, sessionKey, message, attachments);
     },
     [handleSend, stopVoiceReplyPlayback]
   );
@@ -1779,11 +1779,12 @@ const AgentsPageScreen = () => {
                           handleThinkingTracesToggle(focusedAgent.agentId, enabled)
                         }
                         onDraftChange={(value) => handleDraftChange(focusedAgent.agentId, value)}
-                        onSend={(message) =>
+                        onSend={(message, attachments) =>
                           handleChatSend(
                             focusedAgent.agentId,
                             focusedAgent.sessionKey,
-                            message
+                            message,
+                            attachments
                           )
                         }
                         onRemoveQueuedMessage={(index) =>
diff --git a/src/features/office/screens/OfficeScreen.tsx b/src/features/office/screens/OfficeScreen.tsx
index 1867511..11356da 100644
--- a/src/features/office/screens/OfficeScreen.tsx
+++ b/src/features/office/screens/OfficeScreen.tsx
@@ -1102,6 +1102,7 @@ export function OfficeScreen({
   const previousGatewayStatusRef = useRef<"disconnected" | "connecting" | "connected">(
     "disconnected",
   );
+  const didAutoNavigateFromLobbyRef = useRef(false);
   const [floorRosterCache, setFloorRosterCache] = useState(() =>
     createFloorRosterCache(),
   );
@@ -1162,10 +1163,20 @@ export function OfficeScreen({
     };
   }, [settingsCoordinator]);
 
+  // Reset auto-navigate flag when disconnected so the next connection can navigate again.
   useEffect(() => {
-    const previousStatus = previousGatewayStatusRef.current;
-    previousGatewayStatusRef.current = status;
-    if (previousStatus === "connected" || status !== "connected") return;
+    if (status !== "connected" && status !== "connecting") {
+      didAutoNavigateFromLobbyRef.current = false;
+    }
+  }, [status]);
+
+  // Auto-navigate away from lobby when a real adapter connects.
+  // Uses a ref flag instead of previousGatewayStatusRef so the effect can
+  // re-run when detectedAdapterType arrives in a later render (after status
+  // already flipped to "connected").
+  useEffect(() => {
+    if (status !== "connected") return;
+    if (didAutoNavigateFromLobbyRef.current) return;
     if (activeFloor.kind !== "lobby" || activeFloor.provider !== "demo") return;
 
     const connectedProvider =
@@ -1182,7 +1193,9 @@ export function OfficeScreen({
       ) ?? null;
     if (!targetFloor || targetFloor.id === activeFloor.id) return;
 
+    didAutoNavigateFromLobbyRef.current = true;
     setActiveFloorId(targetFloor.id);
+    setSelectedAdapterType(targetFloor.provider as StudioGatewayAdapterType);
     settingsCoordinator.schedulePatch({ activeFloorId: targetFloor.id }, 0);
   }, [
     activeFloor.id,
@@ -1190,6 +1203,7 @@ export function OfficeScreen({
     activeFloor.provider,
     detectedAdapterType,
     selectedAdapterType,
+    setSelectedAdapterType,
     settingsCoordinator,
     status,
   ]);
diff --git a/src/lib/gateway/GatewayClient.ts b/src/lib/gateway/GatewayClient.ts
index a3040e9..2011106 100644
--- a/src/lib/gateway/GatewayClient.ts
+++ b/src/lib/gateway/GatewayClient.ts
@@ -971,6 +971,7 @@ export const useGatewayConnection = (
           : "openclaw";
       setDetectedAdapterType(nextDetectedAdapterType);
       setHasLastKnownGoodState(nextDetectedAdapterType === selectedAdapterType);
+      // Flush immediately (debounce=0) so lastKnownGood survives a quick refresh.
       settingsCoordinator.schedulePatch({
         gateway: {
           lastKnownGood: {
@@ -979,7 +980,7 @@ export const useGatewayConnection = (
             adapterType: nextDetectedAdapterType,
           },
         },
-      });
+      }, 0);
       gatewayDebugLog("connect:success", {
         selectedAdapterType,
         detectedAdapterType: nextDetectedAdapterType,
diff --git a/src/lib/runtime/types.ts b/src/lib/runtime/types.ts
index 2398566..8947baf 100644
--- a/src/lib/runtime/types.ts
+++ b/src/lib/runtime/types.ts
@@ -6,6 +6,13 @@ import type {
   GatewayStatus,
 } from "@/lib/gateway/GatewayClient";
 
+export type RuntimeAttachment = {
+  name: string;
+  url: string;
+  contentType: string;
+  extractedText?: string | null;
+};
+
 export type RuntimeCapability =
   | "agents"
   | "sessions"