diff --git a/surfsense_web/components/documents/DocumentNode.tsx b/surfsense_web/components/documents/DocumentNode.tsx
index 57a12ab3a..a295696d5 100644
--- a/surfsense_web/components/documents/DocumentNode.tsx
+++ b/surfsense_web/components/documents/DocumentNode.tsx
@@ -89,7 +89,7 @@ export const DocumentNode = React.memo(function DocumentNode({
 	const isProcessing = statusState === "pending" || statusState === "processing";
 	const [dropdownOpen, setDropdownOpen] = useState(false);
 	const [exporting, setExporting] = useState<string | null>(null);
-	const rowRef = useRef<HTMLButtonElement>(null);
+	const rowRef = useRef<HTMLDivElement>(null);
 
 	const handleExport = useCallback(
 		(format: string) => {
@@ -102,8 +102,8 @@ export const DocumentNode = React.memo(function DocumentNode({
 	);
 
 	const attachRef = useCallback(
-		(node: HTMLButtonElement | null) => {
-			(rowRef as React.MutableRefObject<HTMLButtonElement | null>).current = node;
+		(node: HTMLDivElement | null) => {
+			(rowRef as React.MutableRefObject<HTMLDivElement | null>).current = node;
 			drag(node);
 		},
 		[drag]
@@ -112,8 +112,9 @@ export const DocumentNode = React.memo(function DocumentNode({
 	return (
 		<ContextMenu onOpenChange={onContextMenuOpenChange}>
 			<ContextMenuTrigger asChild>
-				<button
-					type="button"
+				<div
+					role="button"
+					tabIndex={0}
 					ref={attachRef}
 					className={cn(
 					"group flex h-8 w-full items-center gap-2.5 rounded-md px-1 text-sm hover:bg-accent/50 cursor-pointer select-none text-left",
@@ -122,6 +123,12 @@ export const DocumentNode = React.memo(function DocumentNode({
 					)}
 					style={{ paddingLeft: `${depth * 16 + 4}px` }}
 					onClick={handleCheckChange}
+					onKeyDown={(e) => {
+						if (e.key === "Enter" || e.key === " ") {
+							e.preventDefault();
+							handleCheckChange();
+						}
+					}}
 				>
 				{(() => {
 					if (statusState === "pending") {
@@ -231,7 +238,7 @@ export const DocumentNode = React.memo(function DocumentNode({
 							</DropdownMenuItem>
 						</DropdownMenuContent>
 					</DropdownMenu>
-				</button>
+				</div>
 			</ContextMenuTrigger>
 
 			{contextMenuOpen && (
diff --git a/surfsense_web/components/documents/FolderNode.tsx b/surfsense_web/components/documents/FolderNode.tsx
index cb314effb..5a76e882d 100644
--- a/surfsense_web/components/documents/FolderNode.tsx
+++ b/surfsense_web/components/documents/FolderNode.tsx
@@ -14,6 +14,8 @@ import {
 import React, { useCallback, useEffect, useRef, useState } from "react";
 import { useDrag, useDrop } from "react-dnd";
 import { Button } from "@/components/ui/button";
+import { Checkbox } from "@/components/ui/checkbox";
+import type { FolderSelectionState } from "./FolderTreeView";
 import {
 	ContextMenu,
 	ContextMenuContent,
@@ -49,6 +51,8 @@ interface FolderNodeProps {
 	isExpanded: boolean;
 	isRenaming: boolean;
 	childCount: number;
+	selectionState: FolderSelectionState;
+	onToggleSelect: (folderId: number, selectAll: boolean) => void;
 	onToggleExpand: (folderId: number) => void;
 	onRename: (folder: FolderDisplay, newName: string) => void;
 	onStartRename: (folderId: number) => void;
@@ -88,6 +92,8 @@ export const FolderNode = React.memo(function FolderNode({
 	isExpanded,
 	isRenaming,
 	childCount,
+	selectionState,
+	onToggleSelect,
 	onToggleExpand,
 	onRename,
 	onStartRename,
@@ -212,6 +218,10 @@ export const FolderNode = React.memo(function FolderNode({
 		onStartRename(folder.id);
 	}, [folder, onStartRename]);
 
+	const handleCheckChange = useCallback(() => {
+		onToggleSelect(folder.id, selectionState !== "all");
+	}, [folder.id, selectionState, onToggleSelect]);
+
 	const FolderIcon = isExpanded ? FolderOpen : Folder;
 
 	return (
@@ -252,6 +262,13 @@ export const FolderNode = React.memo(function FolderNode({
 						)}
 					</span>
 
+					<Checkbox
+						checked={selectionState === "all" ? true : selectionState === "some" ? "indeterminate" : false}
+						onCheckedChange={handleCheckChange}
+						onClick={(e) => e.stopPropagation()}
+						className="h-3.5 w-3.5 shrink-0"
+					/>
+
 					<FolderIcon className="h-4 w-4 shrink-0 text-muted-foreground" />
 
 					{isRenaming ? (
diff --git a/surfsense_web/components/documents/FolderTreeView.tsx b/surfsense_web/components/documents/FolderTreeView.tsx
index d7a82fb0b..eec0aa7cc 100644
--- a/surfsense_web/components/documents/FolderTreeView.tsx
+++ b/surfsense_web/components/documents/FolderTreeView.tsx
@@ -10,6 +10,8 @@ import type { DocumentTypeEnum } from "@/contracts/types/document.types";
 import { DocumentNode, type DocumentNodeDoc } from "./DocumentNode";
 import { type FolderDisplay, FolderNode } from "./FolderNode";
 
+export type FolderSelectionState = "all" | "some" | "none";
+
 interface FolderTreeViewProps {
 	folders: FolderDisplay[];
 	documents: DocumentNodeDoc[];
@@ -20,6 +22,7 @@ interface FolderTreeViewProps {
 		doc: { id: number; title: string; document_type: string },
 		isMentioned: boolean
 	) => void;
+	onToggleFolderSelect: (folderId: number, selectAll: boolean) => void;
 	onRenameFolder: (folder: FolderDisplay, newName: string) => void;
 	onDeleteFolder: (folder: FolderDisplay) => void;
 	onMoveFolder: (folder: FolderDisplay) => void;
@@ -55,6 +58,7 @@ export function FolderTreeView({
 	onToggleExpand,
 	mentionedDocIds,
 	onToggleChatMention,
+	onToggleFolderSelect,
 	onRenameFolder,
 	onDeleteFolder,
 	onMoveFolder,
@@ -122,6 +126,36 @@ export function FolderTreeView({
 		return match;
 	}, [folders, docsByFolder, foldersByParent, activeTypes]);
 
+	const folderSelectionStates = useMemo(() => {
+		const states: Record<number, FolderSelectionState> = {};
+		const isSelectable = (d: DocumentNodeDoc) =>
+			d.status?.state !== "pending" && d.status?.state !== "processing";
+
+		function compute(folderId: number): { selected: number; total: number } {
+			const directDocs = (docsByFolder[folderId] ?? []).filter(isSelectable);
+			let selected = directDocs.filter((d) => mentionedDocIds.has(d.id)).length;
+			let total = directDocs.length;
+
+			for (const child of foldersByParent[folderId] ?? []) {
+				const sub = compute(child.id);
+				selected += sub.selected;
+				total += sub.total;
+			}
+
+			if (total === 0) states[folderId] = "none";
+			else if (selected === total) states[folderId] = "all";
+			else if (selected > 0) states[folderId] = "some";
+			else states[folderId] = "none";
+
+			return { selected, total };
+		}
+
+		for (const f of folders) {
+			if (states[f.id] === undefined) compute(f.id);
+		}
+		return states;
+	}, [folders, docsByFolder, foldersByParent, mentionedDocIds]);
+
 	function renderLevel(parentId: number | null, depth: number): React.ReactNode[] {
 		const key = parentId ?? "root";
 		const childFolders = (foldersByParent[key] ?? [])
@@ -151,6 +185,8 @@ export function FolderTreeView({
 					isExpanded={expandedIds.has(f.id)}
 					isRenaming={renamingFolderId === f.id}
 					childCount={folderChildCounts[f.id] ?? 0}
+					selectionState={folderSelectionStates[f.id] ?? "none"}
+					onToggleSelect={onToggleFolderSelect}
 					onToggleExpand={onToggleExpand}
 					onRename={onRenameFolder}
 					onStartRename={handleStartRename}
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index 1e1e8f982..f4ddf5ce5 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -348,6 +348,43 @@ export function DocumentsSidebar({
 		[setSidebarDocs]
 	);
 
+	const handleToggleFolderSelect = useCallback(
+		(folderId: number, selectAll: boolean) => {
+			function collectSubtreeDocs(parentId: number): DocumentNodeDoc[] {
+				const directDocs = (treeDocuments ?? []).filter(
+					(d) =>
+						d.folderId === parentId &&
+						d.status?.state !== "pending" &&
+						d.status?.state !== "processing",
+				);
+				const childFolders = foldersByParent[String(parentId)] ?? [];
+				const descendantDocs = childFolders.flatMap((cf) => collectSubtreeDocs(cf.id));
+				return [...directDocs, ...descendantDocs];
+			}
+
+			const subtreeDocs = collectSubtreeDocs(folderId);
+			if (subtreeDocs.length === 0) return;
+
+			if (selectAll) {
+				setSidebarDocs((prev) => {
+					const existingIds = new Set(prev.map((d) => d.id));
+					const newDocs = subtreeDocs
+						.filter((d) => !existingIds.has(d.id))
+						.map((d) => ({
+							id: d.id,
+							title: d.title,
+							document_type: d.document_type as DocumentTypeEnum,
+						}));
+					return newDocs.length > 0 ? [...prev, ...newDocs] : prev;
+				});
+			} else {
+				const idsToRemove = new Set(subtreeDocs.map((d) => d.id));
+				setSidebarDocs((prev) => prev.filter((d) => !idsToRemove.has(d.id)));
+			}
+		},
+		[treeDocuments, foldersByParent, setSidebarDocs],
+	);
+
 	const isSearchMode = !!debouncedSearch.trim();
 
 	const {
@@ -625,6 +662,7 @@ export function DocumentsSidebar({
 						onToggleExpand={toggleFolderExpand}
 						mentionedDocIds={mentionedDocIds}
 						onToggleChatMention={handleToggleChatMention}
+						onToggleFolderSelect={handleToggleFolderSelect}
 						onRenameFolder={handleRenameFolder}
 						onDeleteFolder={handleDeleteFolder}
 						onMoveFolder={handleMoveFolder}