diff --git a/surfsense_web/components/assistant-ui/connector-popup.tsx b/surfsense_web/components/assistant-ui/connector-popup.tsx
index f234f46eb..e0b2e475f 100644
--- a/surfsense_web/components/assistant-ui/connector-popup.tsx
+++ b/surfsense_web/components/assistant-ui/connector-popup.tsx
@@ -4,7 +4,7 @@ import { useAtomValue } from "jotai";
 import { AlertTriangle, Cable, Settings } from "lucide-react";
 import Link from "next/link";
 import { useSearchParams } from "next/navigation";
-import { type FC, useMemo } from "react";
+import { type FC, forwardRef, useImperativeHandle, useMemo } from "react";
 import { documentTypeCountsAtom } from "@/atoms/documents/document-query.atoms";
 import {
 	globalNewLLMConfigsAtom,
@@ -37,7 +37,16 @@ import { AllConnectorsTab } from "./connector-popup/tabs/all-connectors-tab";
 import { ConnectorAccountsListView } from "./connector-popup/views/connector-accounts-list-view";
 import { YouTubeCrawlerView } from "./connector-popup/views/youtube-crawler-view";
 
-export const ConnectorIndicator: FC = () => {
+export interface ConnectorIndicatorHandle {
+	open: () => void;
+}
+
+interface ConnectorIndicatorProps {
+	showTrigger?: boolean;
+}
+
+export const ConnectorIndicator = forwardRef<ConnectorIndicatorHandle, ConnectorIndicatorProps>(
+	({ showTrigger = true }, ref) => {
 	const searchSpaceId = useAtomValue(activeSearchSpaceIdAtom);
 	const searchParams = useSearchParams();
 	const { data: currentUser } = useAtomValue(currentUserAtom);
@@ -189,38 +198,44 @@ export const ConnectorIndicator: FC = () => {
 		(connectors || []).map((c: SearchSourceConnector) => c.connector_type)
 	);
 
+	useImperativeHandle(ref, () => ({
+		open: () => handleOpenChange(true),
+	}));
+
 	if (!searchSpaceId) return null;
 
 	return (
 		<Dialog open={isOpen} onOpenChange={handleOpenChange}>
-			<TooltipIconButton
-				data-joyride="connector-icon"
-				tooltip={hasConnectors ? `Manage ${activeConnectorsCount} connectors` : "Connect your data"}
-				side="bottom"
-				className={cn(
-					"size-[34px] rounded-full p-1 flex items-center justify-center transition-colors relative",
-					"hover:bg-muted-foreground/15 dark:hover:bg-muted-foreground/30",
-					"outline-none focus:outline-none focus-visible:outline-none font-semibold text-xs",
-					"border-0 ring-0 focus:ring-0 shadow-none focus:shadow-none"
-				)}
-				aria-label={
-					hasConnectors ? `View ${activeConnectorsCount} connectors` : "Add your first connector"
-				}
-				onClick={() => handleOpenChange(true)}
-			>
-				{isLoading ? (
-					<Spinner size="sm" />
-				) : (
-					<>
-						<Cable className="size-4 stroke-[1.5px]" />
-						{activeConnectorsCount > 0 && (
-							<span className="absolute -top-0.5 right-0 flex items-center justify-center min-w-[16px] h-4 px-1 text-[10px] font-medium rounded-full bg-primary text-primary-foreground shadow-sm select-none">
-								{activeConnectorsCount > 99 ? "99+" : activeConnectorsCount}
-							</span>
-						)}
-					</>
-				)}
-			</TooltipIconButton>
+			{showTrigger && (
+				<TooltipIconButton
+					data-joyride="connector-icon"
+					tooltip={hasConnectors ? `Manage ${activeConnectorsCount} connectors` : "Connect your data"}
+					side="bottom"
+					className={cn(
+						"size-[34px] rounded-full p-1 flex items-center justify-center transition-colors relative",
+						"hover:bg-muted-foreground/15 dark:hover:bg-muted-foreground/30",
+						"outline-none focus:outline-none focus-visible:outline-none font-semibold text-xs",
+						"border-0 ring-0 focus:ring-0 shadow-none focus:shadow-none"
+					)}
+					aria-label={
+						hasConnectors ? `View ${activeConnectorsCount} connectors` : "Add your first connector"
+					}
+					onClick={() => handleOpenChange(true)}
+				>
+					{isLoading ? (
+						<Spinner size="sm" />
+					) : (
+						<>
+							<Cable className="size-4 stroke-[1.5px]" />
+							{activeConnectorsCount > 0 && (
+								<span className="absolute -top-0.5 right-0 flex items-center justify-center min-w-[16px] h-4 px-1 text-[10px] font-medium rounded-full bg-primary text-primary-foreground shadow-sm select-none">
+									{activeConnectorsCount > 99 ? "99+" : activeConnectorsCount}
+								</span>
+							)}
+						</>
+					)}
+				</TooltipIconButton>
+			)}
 
 			<DialogContent className="max-w-3xl w-[95vw] sm:w-full h-[75vh] sm:h-[85vh] flex flex-col p-0 gap-0 overflow-hidden border border-border ring-0 dark:ring-0 bg-muted dark:bg-muted text-foreground focus:outline-none focus:ring-0 focus-visible:outline-none focus-visible:ring-0 [&>button]:right-4 sm:[&>button]:right-12 [&>button]:top-6 sm:[&>button]:top-10 [&>button]:opacity-80 hover:[&>button]:opacity-100 [&>button_svg]:size-5 select-none">
 				<DialogTitle className="sr-only">Manage Connectors</DialogTitle>
@@ -429,4 +444,6 @@ export const ConnectorIndicator: FC = () => {
 			</DialogContent>
 		</Dialog>
 	);
-};
+});
+
+ConnectorIndicator.displayName = "ConnectorIndicator";
diff --git a/surfsense_web/components/assistant-ui/thread.tsx b/surfsense_web/components/assistant-ui/thread.tsx
index 9646ec036..4281ca2a7 100644
--- a/surfsense_web/components/assistant-ui/thread.tsx
+++ b/surfsense_web/components/assistant-ui/thread.tsx
@@ -14,6 +14,7 @@ import {
 	AlertCircle,
 	ArrowDownIcon,
 	ArrowUpIcon,
+	Cable,
 	CheckIcon,
 	ChevronLeftIcon,
 	ChevronRightIcon,
@@ -22,6 +23,7 @@ import {
 	PlusIcon,
 	RefreshCwIcon,
 	SquareIcon,
+	SquareLibrary,
 } from "lucide-react";
 import { useParams } from "next/navigation";
 import { type FC, useCallback, useContext, useEffect, useMemo, useRef, useState } from "react";
@@ -42,8 +44,10 @@ import {
 import { currentUserAtom } from "@/atoms/user/user-query.atoms";
 import { AssistantMessage } from "@/components/assistant-ui/assistant-message";
 import { ChatSessionStatus } from "@/components/assistant-ui/chat-session-status";
-import { ConnectorIndicator } from "@/components/assistant-ui/connector-popup";
-import { useDocumentUploadDialog } from "@/components/assistant-ui/document-upload-popup";
+import {
+	ConnectorIndicator,
+	type ConnectorIndicatorHandle,
+} from "@/components/assistant-ui/connector-popup";
 import {
 	InlineMentionEditor,
 	type InlineMentionEditorRef,
@@ -62,6 +66,7 @@ import {
 } from "@/components/new-chat/document-mention-picker";
 import type { ThinkingStep } from "@/components/tool-ui/deepagent-thinking";
 import { Button } from "@/components/ui/button";
+import { Popover, PopoverContent, PopoverTrigger } from "@/components/ui/popover";
 import type { Document } from "@/contracts/types/document.types";
 import { useBatchCommentsPreload } from "@/hooks/use-comments";
 import { useCommentsElectric } from "@/hooks/use-comments-electric";
@@ -474,7 +479,8 @@ const ComposerAction: FC<ComposerActionProps> = ({ isBlockedByOtherUser = false
 	const mentionedDocuments = useAtomValue(mentionedDocumentsAtom);
 	const sidebarDocs = useAtomValue(sidebarSelectedDocumentsAtom);
 	const setDocumentsSidebarOpen = useSetAtom(documentsSidebarOpenAtom);
-	const { openDialog: openUploadDialog } = useDocumentUploadDialog();
+	const connectorRef = useRef<ConnectorIndicatorHandle>(null);
+	const [addMenuOpen, setAddMenuOpen] = useState(false);
 
 	const isComposerTextEmpty = useAssistantState(({ composer }) => {
 		const text = composer.text?.trim() || "";
@@ -502,18 +508,53 @@ const ComposerAction: FC<ComposerActionProps> = ({ isBlockedByOtherUser = false
 	return (
 		<div className="aui-composer-action-wrapper relative mx-2 mb-2 flex items-center justify-between">
 			<div className="flex items-center gap-1">
-				<TooltipIconButton
-					tooltip="Upload"
-					side="bottom"
-					variant="ghost"
-					size="icon"
-					className="size-[34px] rounded-full p-1 font-semibold text-xs hover:bg-muted-foreground/15 dark:border-muted-foreground/15 dark:hover:bg-muted-foreground/30"
-					aria-label="Upload documents"
-					onClick={openUploadDialog}
-				>
-					<PlusIcon className="size-4" />
-				</TooltipIconButton>
-				<ConnectorIndicator />
+				<Popover open={addMenuOpen} onOpenChange={setAddMenuOpen}>
+					<PopoverTrigger asChild>
+						<TooltipIconButton
+							tooltip="Configuration"
+							side="bottom"
+							variant="ghost"
+							size="icon"
+							className="size-[34px] rounded-full p-1 font-semibold text-xs hover:bg-muted-foreground/15 dark:border-muted-foreground/15 dark:hover:bg-muted-foreground/30"
+							aria-label="Configuration"
+							data-joyride="connector-icon"
+						>
+							<PlusIcon className="size-4" />
+						</TooltipIconButton>
+					</PopoverTrigger>
+					<PopoverContent
+						side="bottom"
+						align="start"
+						sideOffset={12}
+						className="w-[calc(100vw-2rem)] max-w-60 sm:w-60 p-2"
+					>
+						<div className="flex flex-col gap-0.5">
+							<button
+								type="button"
+								className="flex w-full items-center gap-3 rounded-lg px-3 py-2.5 text-sm font-medium transition-colors hover:bg-accent hover:text-accent-foreground"
+								onClick={() => {
+									setAddMenuOpen(false);
+									setDocumentsSidebarOpen(true);
+								}}
+							>
+								<SquareLibrary className="size-4 shrink-0" />
+								Documents
+							</button>
+							<button
+								type="button"
+								className="flex w-full items-center gap-3 rounded-lg px-3 py-2.5 text-sm font-medium transition-colors hover:bg-accent hover:text-accent-foreground"
+								onClick={() => {
+									setAddMenuOpen(false);
+									connectorRef.current?.open();
+								}}
+							>
+								<Cable className="size-4 shrink-0" />
+								Manage connectors
+							</button>
+						</div>
+					</PopoverContent>
+				</Popover>
+				<ConnectorIndicator ref={connectorRef} showTrigger={false} />
 			</div>
 
 			{!hasModelConfigured && (