diff --git a/src/lib/components/chat/Chat.svelte b/src/lib/components/chat/Chat.svelte
index ab84909a6..5407f307b 100644
--- a/src/lib/components/chat/Chat.svelte
+++ b/src/lib/components/chat/Chat.svelte
@@ -144,6 +144,7 @@
 
 	let selectedToolIds = [];
 	let selectedFilterIds = [];
+	let pendingOAuthTools = [];
 
 	let imageGenerationEnabled = false;
 	let webSearchEnabled = false;
@@ -274,6 +275,7 @@
 	const resetInput = () => {
 		selectedToolIds = [];
 		selectedFilterIds = [];
+		pendingOAuthTools = [];
 		webSearchEnabled = false;
 		imageGenerationEnabled = false;
 		codeInterpreterEnabled = false;
@@ -298,11 +300,28 @@
 		if (model) {
 			// Set Default Tools
 			if (model?.info?.meta?.toolIds) {
-				selectedToolIds = [
+				const defaultIds = [
 					...new Set(
 						[...(model?.info?.meta?.toolIds ?? [])].filter((id) => $tools.find((t) => t.id === id))
 					)
 				];
+
+				// Separate unauthenticated OAuth tools
+				const unauthed = [];
+				const authed = [];
+				for (const id of defaultIds) {
+					const tool = $tools.find((t) => t.id === id);
+					if (tool && tool.authenticated === false) {
+						const parts = id.split(':');
+						const serverId = parts.at(-1) ?? id;
+						const authType = parts.length > 1 ? parts[0] === 'server' ? parts[1] : parts[0] : null;
+						unauthed.push({ id, name: tool.name ?? id, serverId, authType });
+					} else {
+						authed.push(id);
+					}
+				}
+				selectedToolIds = authed;
+				pendingOAuthTools = unauthed;
 			} else if ($settings?.tools) {
 				selectedToolIds = $settings.tools;
 			} else {
@@ -1765,6 +1784,12 @@
 			selectedModels = _selectedModels;
 		}
 
+		if (pendingOAuthTools.length > 0) {
+			toast.warning(
+				$i18n.t('Please connect all required integrations before sending a message')
+			);
+			return;
+		}
 		if (userPrompt === '' && files.length === 0) {
 			toast.error($i18n.t('Please enter a prompt'));
 			return;
@@ -2843,6 +2868,7 @@
 									bind:selectedFilterIds
 									bind:imageGenerationEnabled
 									bind:codeInterpreterEnabled
+									{pendingOAuthTools}
 									bind:webSearchEnabled
 									bind:atSelectedModel
 									bind:showCommands
@@ -2930,6 +2956,7 @@
 									bind:atSelectedModel
 									bind:showCommands
 									bind:dragged
+									{pendingOAuthTools}
 									toolServers={$toolServers}
 									{stopResponse}
 									{createMessagePair}
diff --git a/src/lib/components/chat/MessageInput.svelte b/src/lib/components/chat/MessageInput.svelte
index 1c8ee493f..602200dee 100644
--- a/src/lib/components/chat/MessageInput.svelte
+++ b/src/lib/components/chat/MessageInput.svelte
@@ -60,6 +60,7 @@
 	import { getTools } from '$lib/apis/tools';
 
 	import { WEBUI_BASE_URL, WEBUI_API_BASE_URL, PASTED_TEXT_CHARACTER_LIMIT } from '$lib/constants';
+	import { getOAuthClientAuthorizationUrl } from '$lib/apis/configs';
 
 	import { createNoteHandler } from '../notes/utils';
 	import { getSuggestionRenderer } from '../common/RichTextInput/suggestions';
@@ -130,6 +131,8 @@
 	export let webSearchEnabled = false;
 	export let codeInterpreterEnabled = false;
 
+	export let pendingOAuthTools = [];
+
 	let showTerminalMenu = false;
 
 	export let messageQueue: { id: string; prompt: string; files: any[] }[] = [];
@@ -1800,6 +1803,27 @@
 												</button>
 											</Tooltip>
 										{/if}
+
+										{#each pendingOAuthTools as pendingTool (pendingTool.id)}
+											<Tooltip content={$i18n.t('Click to connect')} placement="top">
+												<button
+													on:click|preventDefault={() => {
+														sessionStorage.setItem('pendingOAuthToolId', pendingTool.id);
+														const authUrl = getOAuthClientAuthorizationUrl(
+															pendingTool.serverId,
+															pendingTool.authType ?? 'mcp'
+														);
+														window.open(authUrl, '_self', 'noopener');
+													}}
+													type="button"
+													class="group px-2 py-[5px] flex gap-1.5 items-center text-xs rounded-full transition-colors duration-300 focus:outline-hidden max-w-full overflow-hidden
+														text-amber-600 dark:text-amber-400 bg-amber-50 hover:bg-amber-100 dark:bg-amber-400/10 dark:hover:bg-amber-600/10 border border-amber-200/40 dark:border-amber-500/20"
+												>
+													<Wrench className="size-3.5" strokeWidth="1.75" />
+													<span class="truncate">{pendingTool.name}</span>
+												</button>
+											</Tooltip>
+										{/each}
 									</div>
 								</div>
 
diff --git a/src/lib/components/chat/Placeholder.svelte b/src/lib/components/chat/Placeholder.svelte
index b7236dc60..c9816b7fb 100644
--- a/src/lib/components/chat/Placeholder.svelte
+++ b/src/lib/components/chat/Placeholder.svelte
@@ -47,6 +47,7 @@
 
 	export let selectedToolIds = [];
 	export let selectedFilterIds = [];
+	export let pendingOAuthTools = [];
 
 	export let showCommands = false;
 
@@ -218,6 +219,7 @@
 					bind:atSelectedModel
 					bind:showCommands
 					bind:dragged
+					{pendingOAuthTools}
 					{toolServers}
 					{stopResponse}
 					{createMessagePair}