diff --git a/surfsense_web/components/assistant-ui/thread.tsx b/surfsense_web/components/assistant-ui/thread.tsx
index 709b932e6..ab25d28f8 100644
--- a/surfsense_web/components/assistant-ui/thread.tsx
+++ b/surfsense_web/components/assistant-ui/thread.tsx
@@ -549,6 +549,15 @@ const ComposerAction: FC<ComposerActionProps> = ({ isBlockedByOtherUser = false
 					</PopoverContent>
 				</Popover>
 				<ConnectorIndicator ref={connectorRef} showTrigger={false} />
+				{sidebarDocs.length > 0 && (
+					<button
+						type="button"
+						onClick={() => setDocumentsSidebarOpen(true)}
+						className="rounded-full border border-border/60 bg-accent/50 px-2.5 py-1 text-xs font-medium text-foreground/80 transition-colors hover:bg-accent"
+					>
+						{sidebarDocs.length} {sidebarDocs.length === 1 ? "source" : "sources"} selected
+					</button>
+				)}
 			</div>
 
 			{!hasModelConfigured && (
@@ -559,15 +568,6 @@ const ComposerAction: FC<ComposerActionProps> = ({ isBlockedByOtherUser = false
 			)}
 
 			<div className="flex items-center gap-2">
-				{sidebarDocs.length > 0 && (
-					<button
-						type="button"
-						onClick={() => setDocumentsSidebarOpen(true)}
-						className="rounded-full border border-border/60 bg-accent/50 px-2.5 py-1 text-xs font-medium text-foreground/80 transition-colors hover:bg-accent"
-					>
-						{sidebarDocs.length} {sidebarDocs.length === 1 ? "source" : "sources"} selected
-					</button>
-				)}
 
 				<AssistantIf condition={({ thread }) => !thread.isRunning}>
 					<ComposerPrimitive.Send asChild disabled={isSendDisabled}>
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index 25e333b24..c59e39b57 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -1,6 +1,6 @@
 "use client";
 
-import { useAtom, useAtomValue } from "jotai";
+import { useAtom, useAtomValue, useSetAtom } from "jotai";
 import { ChevronLeft, ChevronRight } from "lucide-react";
 import { useParams } from "next/navigation";
 import { useTranslations } from "next-intl";
@@ -12,9 +12,12 @@ import {
 	type SortKey,
 } from "@/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell";
 import { sidebarSelectedDocumentsAtom } from "@/atoms/chat/mentioned-documents.atom";
+import { connectorDialogOpenAtom } from "@/atoms/connector-dialog/connector-dialog.atoms";
 import { deleteDocumentMutationAtom } from "@/atoms/documents/document-mutation.atoms";
 import { Button } from "@/components/ui/button";
+import { Avatar, AvatarFallback, AvatarGroup } from "@/components/ui/avatar";
 import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
+import { getConnectorIcon } from "@/contracts/enums/connectorIcons";
 import type { DocumentTypeEnum } from "@/contracts/types/document.types";
 import { useDebouncedValue } from "@/hooks/use-debounced-value";
 import { useDocumentSearch } from "@/hooks/use-document-search";
@@ -22,6 +25,14 @@ import { useDocuments } from "@/hooks/use-documents";
 import { useMediaQuery } from "@/hooks/use-media-query";
 import { SidebarSlideOutPanel } from "./SidebarSlideOutPanel";
 
+const SHOWCASE_CONNECTORS = [
+	{ type: "GOOGLE_DRIVE_CONNECTOR", label: "Google Drive" },
+	{ type: "GOOGLE_GMAIL_CONNECTOR", label: "Gmail" },
+	{ type: "NOTION_CONNECTOR", label: "Notion" },
+	{ type: "YOUTUBE_CONNECTOR", label: "YouTube" },
+	{ type: "SLACK_CONNECTOR", label: "Slack" },
+] as const;
+
 interface DocumentsSidebarProps {
 	open: boolean;
 	onOpenChange: (open: boolean) => void;
@@ -35,6 +46,7 @@ export function DocumentsSidebar({ open, onOpenChange, isDocked = false, onDocke
 	const params = useParams();
 	const isMobile = !useMediaQuery("(min-width: 640px)");
 	const searchSpaceId = Number(params.search_space_id);
+	const setConnectorDialogOpen = useSetAtom(connectorDialogOpenAtom);
 
 	const [search, setSearch] = useState("");
 	const debouncedSearch = useDebouncedValue(search, 250);
@@ -201,6 +213,38 @@ export function DocumentsSidebar({ open, onOpenChange, isDocked = false, onDocke
 				</div>
 			</div>
 
+		{/* Connected tools strip */}
+			<div className="shrink-0 mx-4 mb-3 flex items-center gap-2 rounded-lg border bg-muted/50 px-3 py-2">
+				<button
+					type="button"
+					onClick={() => setConnectorDialogOpen(true)}
+					className="flex items-center gap-2 min-w-0 flex-1 text-left"
+				>
+					<span className="truncate text-xs text-muted-foreground">
+						Connect your tools
+					</span>
+					<AvatarGroup className="ml-auto shrink-0">
+						{SHOWCASE_CONNECTORS.map(({ type, label }, i) => (
+							<Tooltip key={type}>
+								<TooltipTrigger asChild>
+									<Avatar
+										className="size-6"
+										style={{ zIndex: SHOWCASE_CONNECTORS.length - i }}
+									>
+										<AvatarFallback className="bg-muted text-[10px]">
+											{getConnectorIcon(type, "size-3.5")}
+										</AvatarFallback>
+									</Avatar>
+								</TooltipTrigger>
+								<TooltipContent side="top" className="text-xs">
+									{label}
+								</TooltipContent>
+							</Tooltip>
+						))}
+					</AvatarGroup>
+				</button>
+			</div>
+
 			<div className="flex-1 min-h-0 overflow-x-hidden pt-0 flex flex-col">
 				<div className="px-4 pb-2">
 					<DocumentsFilters
diff --git a/surfsense_web/components/ui/avatar.tsx b/surfsense_web/components/ui/avatar.tsx
index 8261f76a0..6e64f5778 100644
--- a/surfsense_web/components/ui/avatar.tsx
+++ b/surfsense_web/components/ui/avatar.tsx
@@ -38,4 +38,27 @@ function AvatarFallback({
 	);
 }
 
-export { Avatar, AvatarImage, AvatarFallback };
+function AvatarGroup({ className, ...props }: React.ComponentProps<"div">) {
+	return (
+		<div
+			data-slot="avatar-group"
+			className={cn("flex -space-x-2", className)}
+			{...props}
+		/>
+	);
+}
+
+function AvatarGroupCount({ className, ...props }: React.ComponentProps<"span">) {
+	return (
+		<span
+			data-slot="avatar-group-count"
+			className={cn(
+				"relative flex size-8 shrink-0 items-center justify-center rounded-full border-2 border-background bg-muted text-xs font-medium text-muted-foreground",
+				className
+			)}
+			{...props}
+		/>
+	);
+}
+
+export { Avatar, AvatarImage, AvatarFallback, AvatarGroup, AvatarGroupCount };