diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index d5e1d2db6f..e7e442e9d1 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -3043,7 +3043,9 @@ async def process_chat_payload(request, form_data, user, metadata, model):
 
         if direct_tool_servers:
             for tool_server in direct_tool_servers:
-                system_prompt = tool_server.pop('system_prompt', None)
+                if tool_server.get('is_terminal') is True and not terminal_capability:
+                    continue
+                system_prompt = tool_server.get('system_prompt')
                 if system_prompt:
                     form_data['messages'] = add_or_update_system_message(
                         system_prompt,
@@ -3051,7 +3053,7 @@ async def process_chat_payload(request, form_data, user, metadata, model):
                         append=True,
                     )
 
-                tool_specs = tool_server.pop('specs', [])
+                tool_specs = tool_server.get('specs', [])
 
                 for tool in tool_specs:
                     tools_dict[tool['name']] = {
@@ -3107,6 +3109,50 @@ async def process_chat_payload(request, form_data, user, metadata, model):
                 if name not in tools_dict:
                     tools_dict[name] = tool_dict
 
+        # Only advertise user-shell tools when the originating browser has a connected shell.
+        shell_tools = {
+            name: tool
+            for name, tool in tools_dict.items()
+            if name in {'read_user_terminal', 'send_user_terminal_input'}
+            and (tool.get('type') == 'terminal' or tool.get('server', {}).get('is_terminal') is True)
+        }
+        selected = {
+            name
+            for name, tool in shell_tools.items()
+            if terminal_id
+            and (
+                tool.get('tool_id') == f'terminal:{terminal_id}'
+                or (tool.get('direct') and tool.get('server', {}).get('url') == terminal_id)
+            )
+        }
+        connected = False
+        if (
+            selected
+            and event_caller
+            and metadata.get('session_id')
+            and metadata.get('chat_id')
+            and not metadata.get('automation_id')
+            and not metadata.get('internal')
+        ):
+            try:
+                state = await asyncio.wait_for(
+                    event_caller(
+                        {
+                            'type': 'request:terminal:state',
+                            'data': {'terminal_id': terminal_id, 'session_id': metadata['session_id']},
+                        }
+                    ),
+                    timeout=2,
+                )
+                connected = isinstance(state, dict) and state.get('connected') is True
+            except Exception:
+                # Old/disconnected browsers cannot confirm availability; other tools still work.
+                pass
+
+        for name in shell_tools:
+            if not connected or name not in selected:
+                tools_dict.pop(name)
+
         if tools_dict:
             # Always store resolved tools in metadata so downstream consumers
             # (e.g. pipe functions) can access all tools including MCP and builtins.
diff --git a/src/lib/components/chat/Chat.svelte b/src/lib/components/chat/Chat.svelte
index 99b0e8a0f3..fe577388ca 100644
--- a/src/lib/components/chat/Chat.svelte
+++ b/src/lib/components/chat/Chat.svelte
@@ -3579,7 +3579,11 @@
 						(server, idx) => toolServerIds.includes(idx) || toolServerIds.includes(server?.id)
 					),
 					// Direct terminal servers — always included when enabled (not routed through selectedToolIds)
-					...($terminalServers ?? []).filter((t) => !t.id)
+					...(terminalEnabled
+						? ($terminalServers ?? [])
+								.filter((server) => !server.id)
+								.map((server) => ({ ...server, is_terminal: true }))
+						: [])
 				],
 				features: getFeatures(),
 				variables: {
diff --git a/src/lib/components/chat/XTerminal.svelte b/src/lib/components/chat/XTerminal.svelte
index 492d842402..d9163812ed 100644
--- a/src/lib/components/chat/XTerminal.svelte
+++ b/src/lib/components/chat/XTerminal.svelte
@@ -5,6 +5,7 @@
 	import { WebLinksAddon } from '@xterm/addon-web-links';
 	import '@xterm/xterm/css/xterm.css';
 	import { terminalRequest, type TerminalConnection } from '$lib/apis/terminal';
+	import { connectedUserTerminals } from '$lib/stores';
 
 	export let connection: TerminalConnection;
 	export let chatId: string | null = null;
@@ -22,6 +23,17 @@
 	let pingInterval: ReturnType<typeof setInterval>;
 	let destroyed = false;
 	let sessionId = '';
+	const terminalOwner = Symbol();
+
+	function disconnect() {
+		connectedUserTerminals.update((entries) => {
+			entries.delete(terminalOwner);
+			return entries;
+		});
+		connected = false;
+		connecting = false;
+		clearInterval(pingInterval);
+	}
 
 	export function write(output: string) {
 		if (!term || destroyed) return;
@@ -59,9 +71,14 @@
 			ws = new WebSocket(url);
 			ws.binaryType = 'arraybuffer';
 			ws.onopen = () => {
+				if (destroyed) return;
 				ws?.send(
 					JSON.stringify({ type: 'auth', token: connection.key.trim(), chat_id: chatId ?? '' })
 				);
+				if (connection.selector && chatId) {
+					const shell = { terminalId: connection.selector, chatId };
+					connectedUserTerminals.update((entries) => entries.set(terminalOwner, shell));
+				}
 				connected = true;
 				connecting = false;
 				fit();
@@ -72,21 +89,23 @@
 				}, 25000);
 			};
 			ws.onmessage = (event) => {
+				if (destroyed) return;
 				if (event.data instanceof ArrayBuffer) term?.write(new Uint8Array(event.data));
 				else write(event.data);
 			};
 			ws.onclose = () => {
-				connected = false;
-				connecting = false;
-				clearInterval(pingInterval);
+				if (destroyed) return;
+				disconnect();
 				write('\r\n\x1b[90m[Connection closed]\x1b[0m\r\n');
 			};
 			ws.onerror = () => {
-				connecting = false;
+				if (destroyed) return;
+				disconnect();
 				write('\r\n\x1b[31m[Terminal connection failed]\x1b[0m\r\n');
 			};
 		} catch (error) {
-			connecting = false;
+			if (destroyed) return;
+			disconnect();
 			write(`\r\n\x1b[31m[${error}]\x1b[0m\r\n`);
 		}
 	}
@@ -133,7 +152,7 @@
 
 	onDestroy(() => {
 		destroyed = true;
-		clearInterval(pingInterval);
+		disconnect();
 		ws?.close();
 		resizeObserver?.disconnect();
 		term?.dispose();
diff --git a/src/lib/stores/index.ts b/src/lib/stores/index.ts
index e1db1daf59..00fb0d887f 100644
--- a/src/lib/stores/index.ts
+++ b/src/lib/stores/index.ts
@@ -146,6 +146,9 @@ export type FileNavOpenRequest = string | { path: string; page?: number | null }
 export const showFileNavPath: Writable<FileNavOpenRequest | null> = writable(null);
 export const showFileNavDir: Writable<string | null> = writable(null);
 export const selectedTerminalId: Writable<string | null> = writable(null);
+export const connectedUserTerminals = writable(
+	new Map<symbol, { terminalId: string; chatId: string }>()
+);
 
 export const artifactCode = writable(null);
 export const artifactContents = writable(null);
diff --git a/src/routes/+layout.svelte b/src/routes/+layout.svelte
index 094cea1deb..71221fba94 100644
--- a/src/routes/+layout.svelte
+++ b/src/routes/+layout.svelte
@@ -31,6 +31,7 @@
 		channels,
 		channelId,
 		terminalServers,
+		connectedUserTerminals,
 		showControls,
 		showFileNavPath,
 		showFileNavDir,
@@ -556,6 +557,19 @@
 	};
 
 	const chatEventHandler = async (event, cb) => {
+		// Answer this session's availability check even when another chat is active.
+		if (
+			event?.data?.type === 'request:terminal:state' &&
+			event.data.data?.session_id === $socket?.id
+		) {
+			cb?.({
+				connected: [...$connectedUserTerminals.values()].some(
+					(shell) =>
+						shell.terminalId === event.data.data?.terminal_id && shell.chatId === event.chat_id
+				)
+			});
+			return;
+		}
 		const chat = $page.url.pathname.includes(`/c/${event.chat_id}`);
 
 		// Skip events from temporary chats that are not the current chat.