diff --git a/src/lib/apis/terminal/index.ts b/src/lib/apis/terminal/index.ts
index a01ffa5125..de2e2fd5a6 100644
--- a/src/lib/apis/terminal/index.ts
+++ b/src/lib/apis/terminal/index.ts
@@ -58,13 +58,14 @@ export const getCwd = async (baseUrl: string, apiKey: string, sessionId?: string
 export const listFiles = async (
 	baseUrl: string,
 	apiKey: string,
-	path: string = '/'
+	path: string = '/',
+	sessionId?: string
 ): Promise<FileEntry[] | null> => {
 	// The endpoint uses `directory` as the query param name
 	const url = `${baseUrl.replace(/\/$/, '')}/files/list?directory=${encodeURIComponent(path)}`;
-	const res = await fetch(url, {
-		headers: { Authorization: `Bearer ${apiKey}` }
-	})
+	const headers: Record<string, string> = { Authorization: `Bearer ${apiKey}` };
+	if (sessionId) headers['X-Session-Id'] = sessionId;
+	const res = await fetch(url, { headers })
 		.then(async (res) => {
 			if (!res.ok) throw await res.json();
 			return res.json();
@@ -79,12 +80,13 @@ export const listFiles = async (
 export const readFile = async (
 	baseUrl: string,
 	apiKey: string,
-	path: string
+	path: string,
+	sessionId?: string
 ): Promise<string | null> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/read?path=${encodeURIComponent(path)}`;
-	const res = await fetch(url, {
-		headers: { Authorization: `Bearer ${apiKey}` }
-	}).catch((err) => {
+	const headers: Record<string, string> = { Authorization: `Bearer ${apiKey}` };
+	if (sessionId) headers['X-Session-Id'] = sessionId;
+	const res = await fetch(url, { headers }).catch((err) => {
 		console.error('open-terminal readFile error:', err);
 		return null;
 	});
@@ -106,12 +108,13 @@ export const readFile = async (
 export const downloadFileBlob = async (
 	baseUrl: string,
 	apiKey: string,
-	path: string
+	path: string,
+	sessionId?: string
 ): Promise<{ blob: Blob; filename: string } | null> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/view?path=${encodeURIComponent(path)}`;
-	const res = await fetch(url, {
-		headers: { Authorization: `Bearer ${apiKey}` }
-	}).catch(() => null);
+	const headers: Record<string, string> = { Authorization: `Bearer ${apiKey}` };
+	if (sessionId) headers['X-Session-Id'] = sessionId;
+	const res = await fetch(url, { headers }).catch(() => null);
 
 	if (!res || !res.ok) return null;
 
@@ -123,15 +126,18 @@ export const downloadFileBlob = async (
 export const archiveFromTerminal = async (
 	baseUrl: string,
 	apiKey: string,
-	paths: string[]
+	paths: string[],
+	sessionId?: string
 ): Promise<{ blob: Blob; filename: string } | null> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/archive`;
+	const headers: Record<string, string> = {
+		Authorization: `Bearer ${apiKey}`,
+		'Content-Type': 'application/json'
+	};
+	if (sessionId) headers['X-Session-Id'] = sessionId;
 	const res = await fetch(url, {
 		method: 'POST',
-		headers: {
-			Authorization: `Bearer ${apiKey}`,
-			'Content-Type': 'application/json'
-		},
+		headers,
 		body: JSON.stringify({ paths })
 	}).catch(() => null);
 
@@ -148,14 +154,17 @@ export const uploadToTerminal = async (
 	baseUrl: string,
 	apiKey: string,
 	directory: string,
-	file: File
+	file: File,
+	sessionId?: string
 ): Promise<{ path: string; size: number } | null> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/upload?directory=${encodeURIComponent(directory)}`;
 	const body = new FormData();
 	body.append('file', file);
+	const headers: Record<string, string> = { Authorization: `Bearer ${apiKey}` };
+	if (sessionId) headers['X-Session-Id'] = sessionId;
 	const res = await fetch(url, {
 		method: 'POST',
-		headers: { Authorization: `Bearer ${apiKey}` },
+		headers,
 		body
 	})
 		.then(async (res) => {
@@ -172,15 +181,18 @@ export const uploadToTerminal = async (
 export const createDirectory = async (
 	baseUrl: string,
 	apiKey: string,
-	path: string
+	path: string,
+	sessionId?: string
 ): Promise<{ path: string } | null> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/mkdir`;
+	const headers: Record<string, string> = {
+		Authorization: `Bearer ${apiKey}`,
+		'Content-Type': 'application/json'
+	};
+	if (sessionId) headers['X-Session-Id'] = sessionId;
 	const res = await fetch(url, {
 		method: 'POST',
-		headers: {
-			Authorization: `Bearer ${apiKey}`,
-			'Content-Type': 'application/json'
-		},
+		headers,
 		body: JSON.stringify({ path })
 	})
 		.then(async (res) => {
@@ -197,12 +209,15 @@ export const createDirectory = async (
 export const deleteEntry = async (
 	baseUrl: string,
 	apiKey: string,
-	path: string
+	path: string,
+	sessionId?: string
 ): Promise<{ path: string; type: string } | null> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/delete?path=${encodeURIComponent(path)}`;
+	const headers: Record<string, string> = { Authorization: `Bearer ${apiKey}` };
+	if (sessionId) headers['X-Session-Id'] = sessionId;
 	const res = await fetch(url, {
 		method: 'DELETE',
-		headers: { Authorization: `Bearer ${apiKey}` }
+		headers
 	})
 		.then(async (res) => {
 			if (!res.ok) throw await res.json();
@@ -247,15 +262,18 @@ export const moveEntry = async (
 	baseUrl: string,
 	apiKey: string,
 	source: string,
-	destination: string
+	destination: string,
+	sessionId?: string
 ): Promise<{ source: string; destination: string } | { error: string }> => {
 	const url = `${baseUrl.replace(/\/$/, '')}/files/move`;
+	const headers: Record<string, string> = {
+		Authorization: `Bearer ${apiKey}`,
+		'Content-Type': 'application/json'
+	};
+	if (sessionId) headers['X-Session-Id'] = sessionId;
 	const res = await fetch(url, {
 		method: 'POST',
-		headers: {
-			Authorization: `Bearer ${apiKey}`,
-			'Content-Type': 'application/json'
-		},
+		headers,
 		body: JSON.stringify({ source, destination })
 	})
 		.then(async (res) => {
diff --git a/src/lib/components/chat/FileNav.svelte b/src/lib/components/chat/FileNav.svelte
index ef2db742aa..988c92669c 100644
--- a/src/lib/components/chat/FileNav.svelte
+++ b/src/lib/components/chat/FileNav.svelte
@@ -331,7 +331,7 @@
 		savedPath = path;
 		pushNavHistory(path);
 
-		const result = await listFiles(terminal.url, terminal.key, path);
+		const result = await listFiles(terminal.url, terminal.key, path, chatId ?? undefined);
 		loading = false;
 
 		// Set working directory on the terminal server (fire-and-forget)
@@ -366,22 +366,22 @@
 		clearFilePreview();
 
 		if (isImage(filePath)) {
-			const result = await downloadFileBlob(terminal.url, terminal.key, filePath);
+			const result = await downloadFileBlob(terminal.url, terminal.key, filePath, chatId ?? undefined);
 			if (result) fileImageUrl = URL.createObjectURL(result.blob);
 		} else if (isVideo(filePath)) {
-			const result = await downloadFileBlob(terminal.url, terminal.key, filePath);
+			const result = await downloadFileBlob(terminal.url, terminal.key, filePath, chatId ?? undefined);
 			if (result) fileVideoUrl = URL.createObjectURL(result.blob);
 		} else if (isAudio(filePath)) {
-			const result = await downloadFileBlob(terminal.url, terminal.key, filePath);
+			const result = await downloadFileBlob(terminal.url, terminal.key, filePath, chatId ?? undefined);
 			if (result) fileAudioUrl = URL.createObjectURL(result.blob);
 		} else if (isPdf(filePath)) {
-			const result = await downloadFileBlob(terminal.url, terminal.key, filePath);
+			const result = await downloadFileBlob(terminal.url, terminal.key, filePath, chatId ?? undefined);
 			if (result) filePdfData = await result.blob.arrayBuffer();
 		} else if (isSqlite(filePath)) {
-			const result = await downloadFileBlob(terminal.url, terminal.key, filePath);
+			const result = await downloadFileBlob(terminal.url, terminal.key, filePath, chatId ?? undefined);
 			if (result) fileSqliteData = await result.blob.arrayBuffer();
 		} else if (isOffice(filePath)) {
-			const result = await downloadFileBlob(terminal.url, terminal.key, filePath);
+			const result = await downloadFileBlob(terminal.url, terminal.key, filePath, chatId ?? undefined);
 			if (result) {
 				const ext = getFileExt(filePath);
 				const arrayBuffer = await result.blob.arrayBuffer();
@@ -414,7 +414,7 @@
 				}
 			}
 		} else {
-			fileContent = await readFile(terminal.url, terminal.key, filePath);
+			fileContent = await readFile(terminal.url, terminal.key, filePath, chatId ?? undefined);
 		}
 		fileLoading = false;
 	};
@@ -427,7 +427,7 @@
 		const isDir = path.endsWith('/');
 		const result = isDir
 			? await archiveFromTerminal(terminal.url, terminal.key, [path.replace(/\/$/, '')])
-			: await downloadFileBlob(terminal.url, terminal.key, path);
+			: await downloadFileBlob(terminal.url, terminal.key, path, chatId ?? undefined);
 		if (!result) return;
 		const url = URL.createObjectURL(result.blob);
 		const a = document.createElement('a');
@@ -459,7 +459,7 @@
 
 		uploading = true;
 		for (const file of droppedFiles) {
-			await uploadToTerminal(terminal.url, terminal.key, currentPath, file);
+			await uploadToTerminal(terminal.url, terminal.key, currentPath, file, chatId ?? undefined);
 		}
 		uploading = false;
 		await loadDir(currentPath);
@@ -471,7 +471,7 @@
 
 		uploading = true;
 		for (const file of files) {
-			await uploadToTerminal(terminal.url, terminal.key, currentPath, file);
+			await uploadToTerminal(terminal.url, terminal.key, currentPath, file, chatId ?? undefined);
 		}
 		uploading = false;
 		await loadDir(currentPath);
@@ -494,7 +494,7 @@
 		const terminal = selectedTerminal;
 		if (!terminal) return;
 
-		const result = await createDirectory(terminal.url, terminal.key, `${currentPath}${name}`);
+		const result = await createDirectory(terminal.url, terminal.key, `${currentPath}${name}`, chatId ?? undefined);
 		toast[result ? 'success' : 'error'](
 			$i18n.t(result ? 'Folder created' : 'Failed to create folder')
 		);
@@ -529,7 +529,7 @@
 		const terminal = selectedTerminal;
 		if (!terminal) return;
 
-		const result = await deleteEntry(terminal.url, terminal.key, path);
+		const result = await deleteEntry(terminal.url, terminal.key, path, chatId ?? undefined);
 		toast[result ? 'success' : 'error'](
 			$i18n.t(result ? '{{name}} deleted' : 'Failed to delete {{name}}', { name })
 		);
@@ -555,7 +555,7 @@
 		const sourceDir = source.endsWith('/') ? source : source + '/';
 		if (destFolder.startsWith(sourceDir)) return;
 
-		const result = await moveEntry(terminal.url, terminal.key, source, destination);
+		const result = await moveEntry(terminal.url, terminal.key, source, destination, chatId ?? undefined);
 		if ('error' in result) {
 			toast.error(result.error);
 		} else {
@@ -574,7 +574,7 @@
 
 		if (oldPath === destination) return;
 
-		const result = await moveEntry(terminal.url, terminal.key, oldPath, destination);
+		const result = await moveEntry(terminal.url, terminal.key, oldPath, destination, chatId ?? undefined);
 		if ('error' in result) {
 			toast.error(result.error);
 		} else {