diff --git a/src/lib/components/chat/Chat.svelte b/src/lib/components/chat/Chat.svelte
index 7c24cb57d4..246b59c61e 100644
--- a/src/lib/components/chat/Chat.svelte
+++ b/src/lib/components/chat/Chat.svelte
@@ -1,4 +1,5 @@
 <script lang="ts">
+	import type { TerminalContext } from '$lib/types';
 	import { v4 as uuidv4 } from 'uuid';
 	import { toast } from 'svelte-sonner';
 
@@ -473,6 +474,7 @@
 	let prompt = '';
 	let chatFiles = [];
 	let files: any[] = [];
+	let terminalContext: TerminalContext | null = null;
 	let params = {};
 	let chatVariables = {};
 	let showChatVariablesModal = false;
@@ -938,6 +940,7 @@
 	};
 
 	const initEmbeddedDraft = async () => {
+		terminalContext = null;
 		clearTimeout(saveControlsTimer);
 		await saveControls();
 
@@ -1062,6 +1065,7 @@
 
 	let lastTerminalSkillSelector: string | null = null;
 	$: if ($selectedTerminalId !== lastTerminalSkillSelector) {
+		terminalContext = null;
 		selectedSkillIds = selectedSkillIds.filter((id) => !id.startsWith('terminal:'));
 		terminalSkills.set([]);
 		lastTerminalSkillSelector = $selectedTerminalId;
@@ -2544,6 +2548,7 @@
 	};
 
 	const initNewChat = async () => {
+		if ($chatId) terminalContext = null;
 		cancelBrowserInteractions();
 		bridge?.end();
 		console.log('initNewChat');
@@ -2787,6 +2792,7 @@
 	};
 
 	const loadChat = async () => {
+		if (chatIdProp && chatIdProp !== $chatId) terminalContext = null;
 		noteChatDebug('loadChat start');
 		// chatIdProp is empty for chats started from the home page (URL set via replaceState)
 		chatId.set(chatIdProp || $chatId);
@@ -5115,6 +5121,7 @@
 									class=" pb-2 {dragged ? 'z-0' : 'z-10'}"
 								>
 									<MessageInput
+										{terminalContext}
 										{typingUsers}
 										on:typing={(event) => emitTyping(event.detail)}
 										callActive={!!(bridge?.connected || bridge?.connecting)}
@@ -5211,6 +5218,7 @@
 								{/if}
 								<div id={embedded ? messageInputDropzoneId : undefined} class="pb-2 z-10">
 									<MessageInput
+										{terminalContext}
 										{typingUsers}
 										on:typing={(event) => emitTyping(event.detail)}
 										callActive={!!(bridge?.connected || bridge?.connecting)}
@@ -5276,6 +5284,7 @@
 						{:else}
 							<div class="flex items-center h-full">
 								<Placeholder
+									{terminalContext}
 									callActive={!!(bridge?.connected || bridge?.connecting)}
 									callEnabled={!isShared}
 									bind:selectedModelIdx
@@ -5332,6 +5341,7 @@
 
 				{#if !embedded}
 					<ChatControls
+						bind:terminalContext
 						bind:history
 						bind:chatFiles
 						bind:params
diff --git a/src/lib/components/chat/ChatControls.svelte b/src/lib/components/chat/ChatControls.svelte
index c8f8e3b0fb..a40b54ade2 100644
--- a/src/lib/components/chat/ChatControls.svelte
+++ b/src/lib/components/chat/ChatControls.svelte
@@ -3,6 +3,7 @@
 </script>
 
 <script lang="ts">
+	import type { TerminalContext } from '$lib/types';
 	import { onMount, tick, getContext } from 'svelte';
 	import {
 		config,
@@ -34,6 +35,7 @@
 	export let models = [];
 
 	export let chatId = null;
+	export let terminalContext: TerminalContext | null = null;
 	export let chatUser = null;
 
 	export let chatFiles = [];
@@ -298,7 +300,7 @@
 									}}
 								/>
 							{:else if activeTab === 'files' && terminalFilesAvailable && $selectedTerminalId}
-								<FileNav {chatId} />
+								<FileNav {chatId} bind:terminalContext />
 							{:else if activeTab === 'files' && codeInterpreterEnabled}
 								<PyodideFileNav />
 							{:else}
@@ -428,7 +430,7 @@
 									}}
 								/>
 							{:else if activeTab === 'files' && terminalFilesAvailable && $selectedTerminalId}
-								<FileNav overlay={dragged} {chatId} />
+								<FileNav overlay={dragged} {chatId} bind:terminalContext />
 							{:else if activeTab === 'files' && codeInterpreterEnabled}
 								<PyodideFileNav overlay={dragged} />
 							{:else}
diff --git a/src/lib/components/chat/FileNav.svelte b/src/lib/components/chat/FileNav.svelte
index 511451d991..dcb3e26a73 100644
--- a/src/lib/components/chat/FileNav.svelte
+++ b/src/lib/components/chat/FileNav.svelte
@@ -12,6 +12,7 @@
 </script>
 
 <script lang="ts">
+	import type { TerminalContext } from '$lib/types';
 	import { toast } from 'svelte-sonner';
 	import Plus from '$lib/components/icons/Plus.svelte';
 	import Folder from '$lib/components/icons/Folder.svelte';
@@ -70,6 +71,7 @@
 
 	export let overlay = false;
 	export let chatId: string | null = null;
+	export let terminalContext: TerminalContext | null = null;
 
 	// ── Terminal panel state ────────────────────────────────────────────
 	let terminalExpanded = false;
@@ -779,6 +781,7 @@
 		clearFilePreview();
 		clearSelection();
 		currentPath = directory;
+		terminalContext = { terminalId: $selectedTerminalId, currentDirectory: directory };
 		savedPath = directory;
 		pushNavHistory(directory);
 
@@ -1552,12 +1555,11 @@
 				terminalEnabled = config?.features?.terminal !== false;
 
 				const serverCwd = await getCwd(terminal.url, terminal.key, chatId ?? undefined);
-				const useServerPath = !!chatId || savedPath === '/';
 				const serverPath = applyCwd(serverCwd);
-				if (useServerPath) {
-					// Fetch session-specific cwd from the server (or global default for new chats)
-					savedPath = serverPath;
-				}
+				savedPath =
+					terminalContext && terminalContext.terminalId === $selectedTerminalId
+						? terminalContext.currentDirectory
+						: serverPath;
 				savedPath = clampToFileRoot(savedPath);
 				loadDir(savedPath, { restoreTree: true });
 			})();
diff --git a/src/lib/components/chat/MessageInput.svelte b/src/lib/components/chat/MessageInput.svelte
index 2191c5a887..45b875569d 100644
--- a/src/lib/components/chat/MessageInput.svelte
+++ b/src/lib/components/chat/MessageInput.svelte
@@ -1,4 +1,5 @@
 <script lang="ts">
+	import type { TerminalContext } from '$lib/types';
 	import { resolveLocalizedFunction } from '$lib/utils/localizedContent';
 	import { functions as localizedFunctions } from '$lib/stores';
 	import DOMPurify from 'dompurify';
@@ -151,6 +152,7 @@
 	export let statusHandler: Function = () => {};
 	export let forkHandler: Function = () => {};
 	export let chatId = '';
+	export let terminalContext: TerminalContext | null = null;
 	export let contextUsage = null;
 	export let contextCompactionEnabled = false;
 	export let embedded = false;
@@ -1014,13 +1016,17 @@
 		if (filesystemUploadTerminal) {
 			try {
 				const cwd =
+					(terminalContext?.terminalId === $selectedTerminalId
+						? terminalContext?.currentDirectory
+						: null) ||
 					(
 						await getCwd(
 							filesystemUploadTerminal.url,
 							filesystemUploadTerminal.key,
 							chatId || undefined
 						)
-					)?.cwd || '/';
+					)?.cwd;
+				if (!cwd) throw new Error($i18n.t('Could not determine the upload folder.'));
 				const uploadedFile = await uploadNewFileToTerminal(
 					filesystemUploadTerminal.url,
 					filesystemUploadTerminal.key,
diff --git a/src/lib/components/chat/Placeholder.svelte b/src/lib/components/chat/Placeholder.svelte
index 71a443c78a..becfd650af 100644
--- a/src/lib/components/chat/Placeholder.svelte
+++ b/src/lib/components/chat/Placeholder.svelte
@@ -1,4 +1,5 @@
 <script lang="ts">
+	import type { TerminalContext } from '$lib/types';
 	import { toast } from 'svelte-sonner';
 	import { marked } from 'marked';
 	import DOMPurify from 'dompurify';
@@ -50,6 +51,7 @@
 
 	export let prompt = '';
 	export let files = [];
+	export let terminalContext: TerminalContext | null = null;
 	export let messageInput = null;
 
 	export let selectedToolIds = [];
@@ -243,6 +245,7 @@
 			<div class="text-base font-normal @md:max-w-3xl w-full py-3 {atSelectedModel ? 'mt-2' : ''}">
 				{#if !($selectedFolder && folderReadOnly)}
 					<MessageInput
+						{terminalContext}
 						{callActive}
 						{callEnabled}
 						bind:this={messageInput}
diff --git a/src/lib/types/index.ts b/src/lib/types/index.ts
index 38acf0d178..604fd3aff5 100644
--- a/src/lib/types/index.ts
+++ b/src/lib/types/index.ts
@@ -14,3 +14,8 @@ export enum TTS_RESPONSE_SPLIT {
 	PARAGRAPHS = 'paragraphs',
 	NONE = 'none'
 }
+
+export type TerminalContext = {
+	terminalId: string | null;
+	currentDirectory: string;
+};