diff --git a/surfsense_web/components/assistant-ui/connector-popup.tsx b/surfsense_web/components/assistant-ui/connector-popup.tsx
index 7184d393f..e838dd02e 100644
--- a/surfsense_web/components/assistant-ui/connector-popup.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup.tsx
@@ -1,12 +1,19 @@
 "use client";
 
 import { useAtomValue } from "jotai";
-import { Cable } from "lucide-react";
+import { AlertTriangle, Cable, Settings } from "lucide-react";
+import Link from "next/link";
 import { useSearchParams } from "next/navigation";
 import type { FC } from "react";
+import {
+	globalNewLLMConfigsAtom,
+	llmPreferencesAtom,
+} from "@/atoms/new-llm-config/new-llm-config-query.atoms";
 import { activeSearchSpaceIdAtom } from "@/atoms/search-spaces/search-space-query.atoms";
 import { currentUserAtom } from "@/atoms/user/user-query.atoms";
 import { TooltipIconButton } from "@/components/assistant-ui/tooltip-icon-button";
+import { Alert, AlertDescription, AlertTitle } from "@/components/ui/alert";
+import { Button } from "@/components/ui/button";
 import { Dialog, DialogContent, DialogTitle } from "@/components/ui/dialog";
 import { Spinner } from "@/components/ui/spinner";
 import { Tabs, TabsContent } from "@/components/ui/tabs";
@@ -34,6 +41,26 @@ export const ConnectorIndicator: FC = () => {
 	const searchSpaceId = useAtomValue(activeSearchSpaceIdAtom);
 	const searchParams = useSearchParams();
 	const { data: currentUser } = useAtomValue(currentUserAtom);
+	const { data: preferences = {}, isFetching: preferencesLoading } =
+		useAtomValue(llmPreferencesAtom);
+	const { data: globalConfigs = [], isFetching: globalConfigsLoading } =
+		useAtomValue(globalNewLLMConfigsAtom);
+
+	// Check if document summary LLM is properly configured
+	// - If ID is 0 (Auto mode), we need global configs to be available
+	// - If ID is positive (user config) or negative (specific global config), it's configured
+	// - If ID is null/undefined, it's not configured
+	const docSummaryLlmId = preferences.document_summary_llm_id;
+	const isAutoMode = docSummaryLlmId === 0;
+	const hasGlobalConfigs = globalConfigs.length > 0;
+
+	const hasDocumentSummaryLLM =
+		docSummaryLlmId !== null &&
+		docSummaryLlmId !== undefined &&
+		// If it's Auto mode, we need global configs to actually be available
+		(!isAutoMode || hasGlobalConfigs);
+
+	const llmConfigLoading = preferencesLoading || globalConfigsLoading;
 
 	// Fetch document type counts using Electric SQL + PGlite for real-time updates
 	const { documentTypeCounts, loading: documentTypesLoading } = useDocumentsElectric(searchSpaceId);
@@ -329,6 +356,27 @@ export const ConnectorIndicator: FC = () => {
 						<div className="flex-1 min-h-0 relative overflow-hidden">
 							<div className="h-full overflow-y-auto" onScroll={handleScroll}>
 								<div className="px-4 sm:px-12 py-4 sm:py-8 pb-12 sm:pb-16">
+									{/* LLM Configuration Warning */}
+									{!llmConfigLoading && !hasDocumentSummaryLLM && (
+										<Alert variant="destructive" className="mb-6">
+											<AlertTriangle className="h-4 w-4" />
+											<AlertTitle>LLM Configuration Required</AlertTitle>
+											<AlertDescription className="mt-2">
+												<p className="mb-3">
+													{isAutoMode && !hasGlobalConfigs
+														? "Auto mode is selected but no global LLM configurations are available. Please configure a custom LLM in Settings to process and summarize documents from your connected sources."
+														: "You need to configure a Document Summary LLM before adding connectors. This LLM is used to process and summarize documents from your connected sources."}
+												</p>
+												<Button asChild size="sm" variant="outline">
+													<Link href={`/dashboard/${searchSpaceId}/settings`}>
+														<Settings className="mr-2 h-4 w-4" />
+														Go to Settings
+													</Link>
+												</Button>
+											</AlertDescription>
+										</Alert>
+									)}
+
 									<TabsContent value="all" className="m-0">
 										<AllConnectorsTab
 											searchQuery={searchQuery}
@@ -338,10 +386,10 @@ export const ConnectorIndicator: FC = () => {
 											allConnectors={connectors}
 											documentTypeCounts={documentTypeCounts}
 											indexingConnectorIds={indexingConnectorIds}
-											onConnectOAuth={handleConnectOAuth}
-											onConnectNonOAuth={handleConnectNonOAuth}
-											onCreateWebcrawler={handleCreateWebcrawler}
-											onCreateYouTubeCrawler={handleCreateYouTubeCrawler}
+											onConnectOAuth={hasDocumentSummaryLLM ? handleConnectOAuth : () => {}}
+											onConnectNonOAuth={hasDocumentSummaryLLM ? handleConnectNonOAuth : () => {}}
+											onCreateWebcrawler={hasDocumentSummaryLLM ? handleCreateWebcrawler : () => {}}
+											onCreateYouTubeCrawler={hasDocumentSummaryLLM ? handleCreateYouTubeCrawler : () => {}}
 											onManage={handleStartEdit}
 											onViewAccountsList={handleViewAccountsList}
 										/>
diff --git a/surfsense_web/components/assistant-ui/document-upload-popup.tsx b/surfsense_web/components/assistant-ui/document-upload-popup.tsx
index abbd5cd1a..b8f2eb1cf 100644
--- a/surfsense_web/components/assistant-ui/document-upload-popup.tsx
+++ b/surfsense_web/components/assistant-ui/document-upload-popup.tsx
@@ -1,7 +1,8 @@
 "use client";
 
 import { useAtomValue } from "jotai";
-import { Upload } from "lucide-react";
+import { AlertTriangle, Settings, Upload } from "lucide-react";
+import Link from "next/link";
 import {
 	createContext,
 	type FC,
@@ -11,8 +12,14 @@ import {
 	useRef,
 	useState,
 } from "react";
+import {
+	globalNewLLMConfigsAtom,
+	llmPreferencesAtom,
+} from "@/atoms/new-llm-config/new-llm-config-query.atoms";
 import { activeSearchSpaceIdAtom } from "@/atoms/search-spaces/search-space-query.atoms";
 import { DocumentUploadTab } from "@/components/sources/DocumentUploadTab";
+import { Alert, AlertDescription, AlertTitle } from "@/components/ui/alert";
+import { Button } from "@/components/ui/button";
 import { Dialog, DialogContent, DialogTitle } from "@/components/ui/dialog";
 
 // Context for opening the dialog from anywhere
@@ -84,6 +91,10 @@ const DocumentUploadPopupContent: FC<{
 	onOpenChange: (open: boolean) => void;
 }> = ({ isOpen, onOpenChange }) => {
 	const searchSpaceId = useAtomValue(activeSearchSpaceIdAtom);
+	const { data: preferences = {}, isFetching: preferencesLoading } =
+		useAtomValue(llmPreferencesAtom);
+	const { data: globalConfigs = [], isFetching: globalConfigsLoading } =
+		useAtomValue(globalNewLLMConfigsAtom);
 
 	if (!searchSpaceId) return null;
 
@@ -91,6 +102,22 @@ const DocumentUploadPopupContent: FC<{
 		onOpenChange(false);
 	};
 
+	// Check if document summary LLM is properly configured
+	// - If ID is 0 (Auto mode), we need global configs to be available
+	// - If ID is positive (user config) or negative (specific global config), it's configured
+	// - If ID is null/undefined, it's not configured
+	const docSummaryLlmId = preferences.document_summary_llm_id;
+	const isAutoMode = docSummaryLlmId === 0;
+	const hasGlobalConfigs = globalConfigs.length > 0;
+
+	const hasDocumentSummaryLLM =
+		docSummaryLlmId !== null &&
+		docSummaryLlmId !== undefined &&
+		// If it's Auto mode, we need global configs to actually be available
+		(!isAutoMode || hasGlobalConfigs);
+
+	const isLoading = preferencesLoading || globalConfigsLoading;
+
 	return (
 		<Dialog open={isOpen} onOpenChange={onOpenChange}>
 			<DialogContent className="max-w-4xl w-[95vw] sm:w-full h-[calc(100dvh-2rem)] sm:h-[85vh] flex flex-col p-0 gap-0 overflow-hidden border border-border bg-muted text-foreground [&>button]:right-3 sm:[&>button]:right-12 [&>button]:top-3 sm:[&>button]:top-10 [&>button]:opacity-80 hover:[&>button]:opacity-100 [&>button]:z-[100] [&>button_svg]:size-4 sm:[&>button_svg]:size-5">
@@ -118,7 +145,27 @@ const DocumentUploadPopupContent: FC<{
 
 					{/* Content */}
 					<div className="px-4 sm:px-12 pb-4 sm:pb-16">
-						<DocumentUploadTab searchSpaceId={searchSpaceId} onSuccess={handleSuccess} />
+						{!isLoading && !hasDocumentSummaryLLM ? (
+							<Alert variant="destructive" className="mb-4">
+								<AlertTriangle className="h-4 w-4" />
+								<AlertTitle>LLM Configuration Required</AlertTitle>
+								<AlertDescription className="mt-2">
+									<p className="mb-3">
+										{isAutoMode && !hasGlobalConfigs
+											? "Auto mode is selected but no global LLM configurations are available. Please configure a custom LLM in Settings to process and summarize your uploaded documents."
+											: "You need to configure a Document Summary LLM before uploading files. This LLM is used to process and summarize your uploaded documents."}
+									</p>
+									<Button asChild size="sm" variant="outline">
+										<Link href={`/dashboard/${searchSpaceId}/settings`}>
+											<Settings className="mr-2 h-4 w-4" />
+											Go to Settings
+										</Link>
+									</Button>
+								</AlertDescription>
+							</Alert>
+						) : (
+							<DocumentUploadTab searchSpaceId={searchSpaceId} onSuccess={handleSuccess} />
+						)}
 					</div>
 				</div>