diff --git a/src/lib/components/chat/FileNav.svelte b/src/lib/components/chat/FileNav.svelte
index f8dfd4f067..a7fb4b7103 100644
--- a/src/lib/components/chat/FileNav.svelte
+++ b/src/lib/components/chat/FileNav.svelte
@@ -465,11 +465,14 @@
 		return isInsideFileRoot(path) ? asDirectoryPath(path) : fileRoot.path;
 	};
 
-	const applyCwd = (cwd: TerminalCwd | null) => {
+	const applyCwd = (cwd: TerminalCwd | null, preferredPath?: string) => {
 		const cwdPath = cwd?.cwd ? asDirectoryPath(cwd.cwd) : null;
 		const homePath = cwd?.home ? asDirectoryPath(cwd.home) : null;
+		const preferredDirectory = preferredPath ? asDirectoryPath(preferredPath) : null;
+		const pathForRoot =
+			preferredDirectory && preferredDirectory !== '/' ? preferredDirectory : cwdPath;
 		const homeRoot =
-			homePath && cwdPath && (cwdPath === homePath || cwdPath.startsWith(homePath))
+			homePath && pathForRoot && (pathForRoot === homePath || pathForRoot.startsWith(homePath))
 				? { path: homePath, label: 'Home' }
 				: undefined;
 		const rootPath = cwd?.root?.path ? asDirectoryPath(cwd.root.path) : null;
@@ -1137,18 +1140,20 @@
 		if (!handledDisplayFile && terminal) {
 			loading = true;
 
-			void (async () => {
-				// Discover server features on initial mount
-				const config = await getTerminalConfig(terminal.url, terminal.key);
-				terminalEnabled = config?.features?.terminal !== false;
+				void (async () => {
+					// Discover server features on initial mount
+					const config = await getTerminalConfig(terminal.url, terminal.key);
+					terminalEnabled = config?.features?.terminal !== false;
 
-				if (chatId || savedPath === '/') {
-					// Fetch session-specific cwd from the server (or global default for new chats)
-					savedPath = applyCwd(await getCwd(terminal.url, terminal.key, chatId ?? undefined));
-				}
-				savedPath = clampToFileRoot(savedPath);
-				loadDir(savedPath, { restoreTree: true });
-			})();
+					const serverCwd = await getCwd(terminal.url, terminal.key, chatId ?? undefined);
+					const serverPath = applyCwd(serverCwd, savedPath);
+					if (chatId || savedPath === '/') {
+						// Fetch session-specific cwd from the server (or global default for new chats)
+						savedPath = serverPath;
+					}
+					savedPath = clampToFileRoot(savedPath);
+					loadDir(savedPath, { restoreTree: true });
+				})();
 		}
 
 		mounted = true;
diff --git a/src/lib/components/chat/FileNav/Icon.svelte b/src/lib/components/chat/FileNav/Icon.svelte
index 1227ad1713..5fa7f4b5a6 100644
--- a/src/lib/components/chat/FileNav/Icon.svelte
+++ b/src/lib/components/chat/FileNav/Icon.svelte
@@ -377,6 +377,28 @@
 			fill="currentColor"
 			stroke="none">PDF</text
 		>
+	{:else if name === 'docx-logo'}
+		<path
+			d="M4 21.4V2.6C4 2.26863 4.26863 2 4.6 2H16.2515C16.4106 2 16.5632 2.06321 16.6757 2.17574L19.8243 5.32426C19.9368 5.43679 20 5.5894 20 5.74853V21.4C20 21.7314 19.7314 22 19.4 22H4.6C4.26863 22 4 21.7314 4 21.4Z"
+		/>
+		<path d="M16 2V5.4C16 5.73137 16.2686 6 16.6 6H20" />
+		<path d="M8 10H16" />
+		<path d="M8 14H16" />
+		<path d="M8 18H13" />
+	{:else if name === 'xlsx-logo'}
+		<path
+			d="M4 21.4V2.6C4 2.26863 4.26863 2 4.6 2H16.2515C16.4106 2 16.5632 2.06321 16.6757 2.17574L19.8243 5.32426C19.9368 5.43679 20 5.5894 20 5.74853V21.4C20 21.7314 19.7314 22 19.4 22H4.6C4.26863 22 4 21.7314 4 21.4Z"
+		/>
+		<path d="M16 2V5.4C16 5.73137 16.2686 6 16.6 6H20" />
+		<path d="M7.5 10H16.5V18H7.5V10Z" />
+		<path d="M7.5 14H16.5" />
+		<path d="M12 10V18" />
+	{:else if name === 'pptx-logo'}
+		<path
+			d="M4 21.4V2.6C4 2.26863 4.26863 2 4.6 2H16.2515C16.4106 2 16.5632 2.06321 16.6757 2.17574L19.8243 5.32426C19.9368 5.43679 20 5.5894 20 5.74853V21.4C20 21.7314 19.7314 22 19.4 22H4.6C4.26863 22 4 21.7314 4 21.4Z"
+		/>
+		<path d="M16 2V5.4C16 5.73137 16.2686 6 16.6 6H20" />
+		<path d="M8 10H16V16H8V10Z" />
 	{:else if name === 'npm'}
 		<path d="M1 8L23 8V15L11 15V17L7.5 17V15L1 15V8Z" />
 		<path d="M7.5 8L7.5 15" />
diff --git a/src/lib/components/chat/FileNav/fileIcon.ts b/src/lib/components/chat/FileNav/fileIcon.ts
index b7c12397dd..4e3454a590 100644
--- a/src/lib/components/chat/FileNav/fileIcon.ts
+++ b/src/lib/components/chat/FileNav/fileIcon.ts
@@ -149,13 +149,14 @@ export function fileIconName(name: string, type: string = 'file'): string {
 		case 'rar':
 			return 'archive';
 		case 'docx':
+			return 'docx-logo';
 		case 'txt':
 			return 'page-text';
 		case 'xlsx':
 		case 'xls':
-			return 'table';
+			return 'xlsx-logo';
 		case 'pptx':
-			return 'page';
+			return 'pptx-logo';
 		default:
 			return 'empty-page';
 	}