diff --git a/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsFilters.tsx b/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsFilters.tsx
index 1cc7d8907..fabbaee39 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsFilters.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsFilters.tsx
@@ -1,20 +1,9 @@
 "use client";
 
-import { CircleAlert, ListFilter, Search, Trash, Upload, X } from "lucide-react";
+import { ListFilter, Search, Upload, X } from "lucide-react";
 import { useTranslations } from "next-intl";
 import React, { useMemo, useRef, useState } from "react";
 import { useDocumentUploadDialog } from "@/components/assistant-ui/document-upload-popup";
-import {
-	AlertDialog,
-	AlertDialogAction,
-	AlertDialogCancel,
-	AlertDialogContent,
-	AlertDialogDescription,
-	AlertDialogFooter,
-	AlertDialogHeader,
-	AlertDialogTitle,
-	AlertDialogTrigger,
-} from "@/components/ui/alert-dialog";
 import { Button } from "@/components/ui/button";
 import { Checkbox } from "@/components/ui/checkbox";
 import { Input } from "@/components/ui/input";
@@ -24,18 +13,14 @@ import { getDocumentTypeIcon, getDocumentTypeLabel } from "./DocumentTypeIcon";
 
 export function DocumentsFilters({
 	typeCounts: typeCountsRecord,
-	selectedIds,
 	onSearch,
 	searchValue,
-	onBulkDelete,
 	onToggleType,
 	activeTypes,
 }: {
 	typeCounts: Partial<Record<DocumentTypeEnum, number>>;
-	selectedIds: Set<number>;
 	onSearch: (v: string) => void;
 	searchValue: string;
-	onBulkDelete: () => Promise<void>;
 	onToggleType: (type: DocumentTypeEnum, checked: boolean) => void;
 	activeTypes: DocumentTypeEnum[];
 }) {
@@ -189,48 +174,6 @@ export function DocumentsFilters({
 					)}
 				</div>
 
-				{/* Bulk Delete Button */}
-				{selectedIds.size > 0 && (
-					<AlertDialog>
-						<AlertDialogTrigger asChild>
-							<Button variant="destructive" size="sm" className="h-9 shrink-0 gap-1.5 px-2.5">
-								<Trash size={14} />
-								<span className="flex h-5 w-5 items-center justify-center rounded-full bg-destructive-foreground/20 text-[10px] font-medium">
-									{selectedIds.size}
-								</span>
-							</Button>
-						</AlertDialogTrigger>
-						<AlertDialogContent className="max-w-md">
-							<div className="flex flex-col gap-2 sm:flex-row sm:gap-4">
-								<div
-									className="flex size-10 shrink-0 items-center justify-center rounded-full bg-destructive/10 text-destructive"
-									aria-hidden="true"
-								>
-									<CircleAlert size={18} strokeWidth={2} />
-								</div>
-								<AlertDialogHeader className="flex-1">
-									<AlertDialogTitle>
-										Delete {selectedIds.size} document{selectedIds.size !== 1 ? "s" : ""}?
-									</AlertDialogTitle>
-									<AlertDialogDescription>
-										This action cannot be undone. This will permanently delete the selected{" "}
-										{selectedIds.size === 1 ? "document" : "documents"} from your search space.
-									</AlertDialogDescription>
-								</AlertDialogHeader>
-							</div>
-							<AlertDialogFooter>
-								<AlertDialogCancel>Cancel</AlertDialogCancel>
-								<AlertDialogAction
-									onClick={onBulkDelete}
-									className="bg-destructive text-destructive-foreground hover:bg-destructive/90"
-								>
-									Delete
-								</AlertDialogAction>
-							</AlertDialogFooter>
-						</AlertDialogContent>
-					</AlertDialog>
-				)}
-
 				{/* Upload Button */}
 				<Button
 					onClick={openUploadDialog}
diff --git a/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx b/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx
index 5925d98f0..08bb7bb21 100644
--- a/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx
+++ b/surfsense_web/app/dashboard/[search_space_id]/documents/(manage)/components/DocumentsTableShell.tsx
@@ -275,8 +275,6 @@ export function DocumentsTableShell({
 	documents,
 	loading,
 	error,
-	selectedIds,
-	setSelectedIds,
 	sortKey,
 	sortDesc,
 	onSortChange,
@@ -286,12 +284,12 @@ export function DocumentsTableShell({
 	loadingMore = false,
 	onLoadMore,
 	isSearchMode = false,
+	mentionedDocIds,
+	onToggleChatMention,
 }: {
 	documents: Document[];
 	loading: boolean;
 	error: boolean;
-	selectedIds: Set<number>;
-	setSelectedIds: (update: Set<number>) => void;
 	sortKey: SortKey;
 	sortDesc: boolean;
 	onSortChange: (key: SortKey) => void;
@@ -301,6 +299,10 @@ export function DocumentsTableShell({
 	loadingMore?: boolean;
 	onLoadMore?: () => void;
 	isSearchMode?: boolean;
+	/** IDs of documents currently mentioned as chips in the chat composer */
+	mentionedDocIds?: Set<number>;
+	/** Toggle a document's mention in the chat (add if not mentioned, remove if mentioned) */
+	onToggleChatMention?: (doc: Document, mentioned: boolean) => void;
 }) {
 	const t = useTranslations("documents");
 	const { openDialog } = useDocumentUploadDialog();
@@ -398,30 +400,28 @@ export function DocumentsTableShell({
 		return state !== "pending" && state !== "processing";
 	};
 
+	const hasChatMode = !!onToggleChatMention && !!mentionedDocIds;
+
 	const selectableDocs = sorted.filter(isSelectable);
-	const allSelectedOnPage =
-		selectableDocs.length > 0 && selectableDocs.every((d) => selectedIds.has(d.id));
-	const someSelectedOnPage =
-		selectableDocs.some((d) => selectedIds.has(d.id)) && !allSelectedOnPage;
+	const allMentionedOnPage =
+		hasChatMode &&
+		selectableDocs.length > 0 &&
+		selectableDocs.every((d) => mentionedDocIds.has(d.id));
+	const someMentionedOnPage =
+		hasChatMode &&
+		selectableDocs.some((d) => mentionedDocIds.has(d.id)) &&
+		!allMentionedOnPage;
 
 	const toggleAll = (checked: boolean) => {
-		const next = new Set(selectedIds);
-		if (checked)
-			selectableDocs.forEach((d) => {
-				next.add(d.id);
-			});
-		else
-			sorted.forEach((d) => {
-				next.delete(d.id);
-			});
-		setSelectedIds(next);
-	};
-
-	const toggleOne = (id: number, checked: boolean) => {
-		const next = new Set(selectedIds);
-		if (checked) next.add(id);
-		else next.delete(id);
-		setSelectedIds(next);
+		if (!onToggleChatMention) return;
+		for (const doc of selectableDocs) {
+			const isMentioned = mentionedDocIds?.has(doc.id) ?? false;
+			if (checked && !isMentioned) {
+				onToggleChatMention(doc, false);
+			} else if (!checked && isMentioned) {
+				onToggleChatMention(doc, true);
+			}
+		}
 	};
 
 	const onSortHeader = (key: SortKey) => onSortChange(key);
@@ -438,9 +438,9 @@ export function DocumentsTableShell({
 							<TableHead className="w-10 pl-3 pr-0 text-center h-8">
 								<div className="flex items-center justify-center h-full">
 									<Checkbox
-										checked={allSelectedOnPage || (someSelectedOnPage && "indeterminate")}
+										checked={allMentionedOnPage || (someMentionedOnPage && "indeterminate")}
 										onCheckedChange={(v) => toggleAll(!!v)}
-										aria-label="Select all"
+										aria-label={hasChatMode ? "Toggle all for chat" : "Select all"}
 										className="border-foreground data-[state=checked]:bg-primary data-[state=checked]:border-primary"
 									/>
 								</div>
@@ -526,58 +526,69 @@ export function DocumentsTableShell({
 					<div ref={desktopScrollRef} className="flex-1 overflow-auto">
 						<Table className="table-fixed w-full">
 							<TableBody>
-								{sorted.map((doc, index) => {
-									const isSelected = selectedIds.has(doc.id);
-									const canSelect = isSelectable(doc);
-									return (
-										<RowContextMenu
-											key={doc.id}
-											doc={doc}
-											onPreview={handleViewDocument}
-											onDelete={setDeleteDoc}
-											searchSpaceId={searchSpaceId}
+							{sorted.map((doc) => {
+								const isMentioned = mentionedDocIds?.has(doc.id) ?? false;
+								const canInteract = isSelectable(doc);
+								const handleRowClick = () => {
+									if (canInteract && onToggleChatMention) {
+										onToggleChatMention(doc, isMentioned);
+									}
+								};
+								return (
+									<RowContextMenu
+										key={doc.id}
+										doc={doc}
+										onPreview={handleViewDocument}
+										onDelete={setDeleteDoc}
+										searchSpaceId={searchSpaceId}
+									>
+										<tr
+											className={`border-b border-border/50 transition-colors ${
+												isMentioned
+													? "bg-primary/5 hover:bg-primary/8"
+													: "hover:bg-muted/30"
+											} ${canInteract && hasChatMode ? "cursor-pointer" : ""}`}
+											onClick={handleRowClick}
 										>
-											<tr
-												className={`border-b border-border/50 transition-colors ${
-													isSelected ? "bg-primary/5 hover:bg-primary/8" : "hover:bg-muted/30"
-												}`}
+											<TableCell
+												className="w-10 pl-3 pr-0 py-1.5 text-center"
+												onClick={(e) => e.stopPropagation()}
 											>
-												<TableCell className="w-10 pl-3 pr-0 py-1.5 text-center">
-													<div className="flex items-center justify-center h-full">
-														<Checkbox
-															checked={isSelected}
-															onCheckedChange={(v) => canSelect && toggleOne(doc.id, !!v)}
-															disabled={!canSelect}
-															aria-label={
-																canSelect ? "Select row" : "Cannot select while processing"
-															}
-															className={`border-foreground data-[state=checked]:bg-primary data-[state=checked]:border-primary ${!canSelect ? "opacity-40 cursor-not-allowed" : ""}`}
-														/>
-													</div>
-												</TableCell>
-												<TableCell className="px-2 py-1.5 max-w-0">
-													<DocumentNameTooltip
-														doc={doc}
-														className="truncate block text-sm text-foreground cursor-default"
+												<div className="flex items-center justify-center h-full">
+													<Checkbox
+														checked={isMentioned}
+														onCheckedChange={() => handleRowClick()}
+														disabled={!canInteract}
+														aria-label={
+															isMentioned ? "Remove from chat" : "Add to chat"
+														}
+														className={`border-foreground data-[state=checked]:bg-primary data-[state=checked]:border-primary ${!canInteract ? "opacity-40 cursor-not-allowed" : ""}`}
 													/>
-												</TableCell>
-												<TableCell className="w-10 px-0 py-1.5 text-center">
-													<Tooltip>
-														<TooltipTrigger asChild>
-															<span className="flex items-center justify-center">
-																{getDocumentTypeIcon(doc.document_type, "h-4 w-4")}
-															</span>
-														</TooltipTrigger>
-														<TooltipContent side="top">
-															{getDocumentTypeLabel(doc.document_type)}
-														</TooltipContent>
-													</Tooltip>
-												</TableCell>
-												<TableCell className="w-12 pl-0 pr-3 py-1.5 text-center">
-													<StatusIndicator status={doc.status} />
-												</TableCell>
-											</tr>
-										</RowContextMenu>
+												</div>
+											</TableCell>
+											<TableCell className="px-2 py-1.5 max-w-0">
+												<DocumentNameTooltip
+													doc={doc}
+													className="truncate block text-sm text-foreground cursor-default"
+												/>
+											</TableCell>
+											<TableCell className="w-10 px-0 py-1.5 text-center">
+												<Tooltip>
+													<TooltipTrigger asChild>
+														<span className="flex items-center justify-center">
+															{getDocumentTypeIcon(doc.document_type, "h-4 w-4")}
+														</span>
+													</TooltipTrigger>
+													<TooltipContent side="top">
+														{getDocumentTypeLabel(doc.document_type)}
+													</TooltipContent>
+												</Tooltip>
+											</TableCell>
+											<TableCell className="w-12 pl-0 pr-3 py-1.5 text-center">
+												<StatusIndicator status={doc.status} />
+											</TableCell>
+										</tr>
+									</RowContextMenu>
 									);
 								})}
 							</TableBody>
@@ -637,50 +648,67 @@ export function DocumentsTableShell({
 					ref={mobileScrollRef}
 					className="md:hidden divide-y divide-border/50 flex-1 overflow-auto"
 				>
-					{sorted.map((doc, index) => {
-						const isSelected = selectedIds.has(doc.id);
-						const canSelect = isSelectable(doc);
-						return (
-							<RowContextMenu
-								key={doc.id}
-								doc={doc}
-								onPreview={handleViewDocument}
-								onDelete={setDeleteDoc}
-								searchSpaceId={searchSpaceId}
-							>
-							<div
-								className={`px-3 py-2 transition-colors ${
-									isSelected ? "bg-primary/5" : "hover:bg-muted/20"
-								}`}
-							>
-									<div className="flex items-center gap-3">
+				{sorted.map((doc) => {
+					const isMentioned = mentionedDocIds?.has(doc.id) ?? false;
+					const canInteract = isSelectable(doc);
+					const handleCardClick = () => {
+						if (canInteract && onToggleChatMention) {
+							onToggleChatMention(doc, isMentioned);
+						}
+					};
+					return (
+						<RowContextMenu
+							key={doc.id}
+							doc={doc}
+							onPreview={handleViewDocument}
+							onDelete={setDeleteDoc}
+							searchSpaceId={searchSpaceId}
+						>
+						<div
+							className={`relative px-3 py-2 transition-colors ${
+								isMentioned
+									? "bg-primary/5"
+									: "hover:bg-muted/20"
+							} ${canInteract && hasChatMode ? "cursor-pointer" : ""}`}
+						>
+								{canInteract && hasChatMode && (
+									<button
+										type="button"
+										className="absolute inset-0 z-0"
+										aria-label={isMentioned ? `Remove ${doc.title} from chat` : `Add ${doc.title} to chat`}
+										onClick={handleCardClick}
+									/>
+								)}
+								<div className="relative z-10 flex items-center gap-3 pointer-events-none">
+									<span className="pointer-events-auto">
 										<Checkbox
-											checked={isSelected}
-											onCheckedChange={(v) => canSelect && toggleOne(doc.id, !!v)}
-											disabled={!canSelect}
-											aria-label={canSelect ? "Select row" : "Cannot select while processing"}
-											className={`border-foreground data-[state=checked]:bg-primary data-[state=checked]:border-primary shrink-0 ${!canSelect ? "opacity-40 cursor-not-allowed" : ""}`}
+											checked={isMentioned}
+											onCheckedChange={() => handleCardClick()}
+											disabled={!canInteract}
+											aria-label={isMentioned ? "Remove from chat" : "Add to chat"}
+											className={`border-foreground data-[state=checked]:bg-primary data-[state=checked]:border-primary shrink-0 ${!canInteract ? "opacity-40 cursor-not-allowed" : ""}`}
+										/>
+									</span>
+									<div className="flex-1 min-w-0">
+										<DocumentNameTooltip
+											doc={doc}
+											className="truncate block text-sm text-foreground cursor-default"
 										/>
-										<div className="flex-1 min-w-0">
-											<DocumentNameTooltip
-												doc={doc}
-												className="truncate block text-sm text-foreground cursor-default"
-											/>
-										</div>
-										<div className="flex items-center gap-2 shrink-0">
-											<Tooltip>
-												<TooltipTrigger asChild>
-													<span className="flex items-center justify-center">
-														{getDocumentTypeIcon(doc.document_type, "h-4 w-4")}
-													</span>
-												</TooltipTrigger>
-												<TooltipContent side="top">
-													{getDocumentTypeLabel(doc.document_type)}
-												</TooltipContent>
-											</Tooltip>
-											<StatusIndicator status={doc.status} />
-										</div>
 									</div>
+									<div className="flex items-center gap-2 shrink-0">
+										<Tooltip>
+											<TooltipTrigger asChild>
+												<span className="flex items-center justify-center">
+													{getDocumentTypeIcon(doc.document_type, "h-4 w-4")}
+												</span>
+											</TooltipTrigger>
+											<TooltipContent side="top">
+												{getDocumentTypeLabel(doc.document_type)}
+											</TooltipContent>
+										</Tooltip>
+										<StatusIndicator status={doc.status} />
+									</div>
+								</div>
 							</div>
 						</RowContextMenu>
 						);
diff --git a/surfsense_web/atoms/chat/mentioned-documents.atom.ts b/surfsense_web/atoms/chat/mentioned-documents.atom.ts
index aba2736e5..4487e1732 100644
--- a/surfsense_web/atoms/chat/mentioned-documents.atom.ts
+++ b/surfsense_web/atoms/chat/mentioned-documents.atom.ts
@@ -1,7 +1,7 @@
 "use client";
 
 import { atom } from "jotai";
-import type { Document, SurfsenseDocsDocument } from "@/contracts/types/document.types";
+import type { Document } from "@/contracts/types/document.types";
 
 /**
  * Atom to store the IDs of documents mentioned in the current chat composer.
@@ -30,6 +30,22 @@ export interface MentionedDocumentInfo {
 	document_type: string;
 }
 
+/**
+ * Queue atom for sidebar → composer communication (additions).
+ * The sidebar writes documents here; the Composer picks them up,
+ * inserts chips, and clears the queue.
+ */
+export const pendingDocumentMentionsAtom = atom<
+	Pick<Document, "id" | "title" | "document_type">[]
+>([]);
+
+/**
+ * Queue atom for sidebar → composer communication (removals).
+ * The sidebar writes { id, document_type } here; the Composer removes
+ * the matching chips and clears the queue.
+ */
+export const pendingDocumentRemovalsAtom = atom<{ id: number; document_type?: string }[]>([]);
+
 /**
  * Atom to store mentioned documents per message ID.
  * This allows displaying which documents were mentioned with each user message.
diff --git a/surfsense_web/components/assistant-ui/inline-mention-editor.tsx b/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
index b4e37d324..cc3ea44af 100644
--- a/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
+++ b/surfsense_web/components/assistant-ui/inline-mention-editor.tsx
@@ -27,6 +27,7 @@ export interface InlineMentionEditorRef {
 	getText: () => string;
 	getMentionedDocuments: () => MentionedDocument[];
 	insertDocumentChip: (doc: Pick<Document, "id" | "title" | "document_type">) => void;
+	removeDocumentChip: (docId: number, docType?: string) => void;
 	setDocumentChipStatus: (
 		docId: number,
 		docType: string | undefined,
@@ -388,6 +389,33 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 			[]
 		);
 
+		const removeDocumentChip = useCallback(
+			(docId: number, docType?: string) => {
+				if (!editorRef.current) return;
+				const chipKey = `${docType ?? "UNKNOWN"}:${docId}`;
+				const chips = editorRef.current.querySelectorAll<HTMLSpanElement>(
+					`span[${CHIP_DATA_ATTR}="true"]`
+				);
+				for (const chip of chips) {
+					if (getChipId(chip) === docId && getChipDocType(chip) === (docType ?? "UNKNOWN")) {
+						chip.remove();
+						break;
+					}
+				}
+				setMentionedDocs((prev) => {
+					const next = new Map(prev);
+					next.delete(chipKey);
+					return next;
+				});
+				onDocumentRemove?.(docId, docType);
+
+				const text = getText();
+				const empty = text.length === 0 && mentionedDocs.size <= 1;
+				setIsEmpty(empty);
+			},
+			[getText, mentionedDocs.size, onDocumentRemove]
+		);
+
 		// Expose methods via ref
 		useImperativeHandle(ref, () => ({
 			focus: () => editorRef.current?.focus(),
@@ -395,6 +423,7 @@ export const InlineMentionEditor = forwardRef<InlineMentionEditorRef, InlineMent
 			getText,
 			getMentionedDocuments,
 			insertDocumentChip,
+			removeDocumentChip,
 			setDocumentChipStatus,
 		}));
 
diff --git a/surfsense_web/components/assistant-ui/thread.tsx b/surfsense_web/components/assistant-ui/thread.tsx
index 31080962c..e5472ccbc 100644
--- a/surfsense_web/components/assistant-ui/thread.tsx
+++ b/surfsense_web/components/assistant-ui/thread.tsx
@@ -32,6 +32,8 @@ import { documentsSidebarOpenAtom } from "@/atoms/documents/ui.atoms";
 import {
 	mentionedDocumentIdsAtom,
 	mentionedDocumentsAtom,
+	pendingDocumentMentionsAtom,
+	pendingDocumentRemovalsAtom,
 } from "@/atoms/chat/mentioned-documents.atom";
 import { membersAtom } from "@/atoms/members/members-query.atoms";
 import {
@@ -229,6 +231,7 @@ const ThreadWelcome: FC = () => {
 const Composer: FC = () => {
 	// Document mention state (atoms persist across component remounts)
 	const [mentionedDocuments, setMentionedDocuments] = useAtom(mentionedDocumentsAtom);
+	const [pendingMentions, setPendingMentions] = useAtom(pendingDocumentMentionsAtom);
 	const [showDocumentPopover, setShowDocumentPopover] = useState(false);
 	const [mentionQuery, setMentionQuery] = useState("");
 	const editorRef = useRef<InlineMentionEditorRef>(null);
@@ -450,6 +453,40 @@ const Composer: FC = () => {
 		[mentionedDocuments, setMentionedDocuments, setMentionedDocumentIds]
 	);
 
+	// Process documents queued from the sidebar (additions)
+	useEffect(() => {
+		if (pendingMentions.length === 0) return;
+		handleDocumentsMention(pendingMentions);
+		setPendingMentions([]);
+	}, [pendingMentions, handleDocumentsMention, setPendingMentions]);
+
+	// Process documents queued from the sidebar (removals)
+	const [pendingRemovals, setPendingRemovals] = useAtom(pendingDocumentRemovalsAtom);
+	useEffect(() => {
+		if (pendingRemovals.length === 0) return;
+		for (const { id, document_type } of pendingRemovals) {
+			editorRef.current?.removeDocumentChip(id, document_type);
+		}
+		setMentionedDocuments((prev) => {
+			const removalKeys = new Set(
+				pendingRemovals.map((r) => `${r.document_type ?? "UNKNOWN"}:${r.id}`)
+			);
+			const updated = prev.filter(
+				(doc) => !removalKeys.has(`${doc.document_type ?? "UNKNOWN"}:${doc.id}`)
+			);
+			setMentionedDocumentIds({
+				surfsense_doc_ids: updated
+					.filter((doc) => doc.document_type === "SURFSENSE_DOCS")
+					.map((doc) => doc.id),
+				document_ids: updated
+					.filter((doc) => doc.document_type !== "SURFSENSE_DOCS")
+					.map((doc) => doc.id),
+			});
+			return updated;
+		});
+		setPendingRemovals([]);
+	}, [pendingRemovals, setPendingRemovals, setMentionedDocuments, setMentionedDocumentIds]);
+
 	return (
 		<ComposerPrimitive.Root className="aui-composer-root relative flex w-full flex-col gap-2">
 			<ChatSessionStatus
diff --git a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
index 74eba6361..cb3abf0e3 100644
--- a/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
+++ b/surfsense_web/components/layout/ui/sidebar/DocumentsSidebar.tsx
@@ -1,11 +1,16 @@
 "use client";
 
-import { useAtomValue } from "jotai";
+import { useAtomValue, useSetAtom } from "jotai";
 import { ChevronLeft } from "lucide-react";
 import { useParams } from "next/navigation";
 import { useTranslations } from "next-intl";
-import { useCallback, useEffect, useRef, useState } from "react";
+import { useCallback, useEffect, useMemo, useRef, useState } from "react";
 import { toast } from "sonner";
+import {
+	mentionedDocumentsAtom,
+	pendingDocumentMentionsAtom,
+	pendingDocumentRemovalsAtom,
+} from "@/atoms/chat/mentioned-documents.atom";
 import { deleteDocumentMutationAtom } from "@/atoms/documents/document-mutation.atoms";
 import { Button } from "@/components/ui/button";
 import type { DocumentTypeEnum } from "@/contracts/types/document.types";
@@ -37,9 +42,30 @@ export function DocumentsSidebar({ open, onOpenChange }: DocumentsSidebarProps)
 	const [activeTypes, setActiveTypes] = useState<DocumentTypeEnum[]>([]);
 	const [sortKey, setSortKey] = useState<SortKey>("created_at");
 	const [sortDesc, setSortDesc] = useState(true);
-	const [selectedIds, setSelectedIds] = useState<Set<number>>(new Set());
 	const { mutateAsync: deleteDocumentMutation } = useAtomValue(deleteDocumentMutationAtom);
 
+	const mentionedDocuments = useAtomValue(mentionedDocumentsAtom);
+	const setPendingMentions = useSetAtom(pendingDocumentMentionsAtom);
+	const setPendingRemovals = useSetAtom(pendingDocumentRemovalsAtom);
+	const mentionedDocIds = useMemo(
+		() => new Set(mentionedDocuments.map((d) => d.id)),
+		[mentionedDocuments]
+	);
+
+	const handleToggleChatMention = useCallback(
+		(doc: { id: number; title: string; document_type: string }, isMentioned: boolean) => {
+			if (isMentioned) {
+				setPendingRemovals((prev) => [...prev, { id: doc.id, document_type: doc.document_type }]);
+			} else {
+				setPendingMentions((prev) => [
+					...prev,
+					{ id: doc.id, title: doc.title, document_type: doc.document_type as DocumentTypeEnum },
+				]);
+			}
+		},
+		[setPendingMentions, setPendingRemovals]
+	);
+
 	const isSearchMode = !!debouncedSearch.trim();
 
 	const {
@@ -76,59 +102,6 @@ export function DocumentsSidebar({ open, onOpenChange }: DocumentsSidebarProps)
 			}
 			return prev.filter((t) => t !== type);
 		});
-		setSelectedIds(new Set());
-	};
-
-	const onBulkDelete = async () => {
-		if (selectedIds.size === 0) {
-			toast.error(t("no_rows_selected"));
-			return;
-		}
-
-		const selectedDocs = displayDocs.filter((doc) => selectedIds.has(doc.id));
-		const deletableIds = selectedDocs
-			.filter((doc) => doc.status?.state !== "pending" && doc.status?.state !== "processing")
-			.map((doc) => doc.id);
-		const inProgressCount = selectedIds.size - deletableIds.length;
-
-		if (inProgressCount > 0) {
-			toast.warning(t("delete_in_progress_warning", { count: inProgressCount }));
-		}
-
-		if (deletableIds.length === 0) return;
-
-		try {
-			let conflictCount = 0;
-			const results = await Promise.all(
-				deletableIds.map(async (id) => {
-					try {
-						await deleteDocumentMutation({ id });
-						return true;
-					} catch (error: unknown) {
-						const status =
-							(error as { response?: { status?: number } })?.response?.status ??
-							(error as { status?: number })?.status;
-						if (status === 409) conflictCount++;
-						return false;
-					}
-				})
-			);
-			const okCount = results.filter((r) => r === true).length;
-			if (okCount === deletableIds.length) {
-				toast.success(t("delete_success_count", { count: okCount }));
-			} else if (conflictCount > 0) {
-				toast.error(t("delete_conflict_error", { count: conflictCount }));
-			} else {
-				toast.error(t("delete_partial_failed"));
-			}
-			if (isSearchMode) {
-				searchRemoveItems(deletableIds);
-			}
-			setSelectedIds(new Set());
-		} catch (e) {
-			console.error(e);
-			toast.error(t("delete_error"));
-		}
 	};
 
 	const handleDeleteDocument = useCallback(
@@ -203,10 +176,8 @@ export function DocumentsSidebar({ open, onOpenChange }: DocumentsSidebarProps)
 				<div className="px-4 pb-2">
 					<DocumentsFilters
 						typeCounts={realtimeTypeCounts}
-						selectedIds={selectedIds}
 						onSearch={setSearch}
 						searchValue={search}
-						onBulkDelete={onBulkDelete}
 						onToggleType={onToggleType}
 						activeTypes={activeTypes}
 					/>
@@ -216,8 +187,6 @@ export function DocumentsSidebar({ open, onOpenChange }: DocumentsSidebarProps)
 					documents={displayDocs}
 					loading={!!loading}
 					error={!!error}
-					selectedIds={selectedIds}
-					setSelectedIds={setSelectedIds}
 					sortKey={sortKey}
 					sortDesc={sortDesc}
 					onSortChange={handleSortChange}
@@ -227,6 +196,8 @@ export function DocumentsSidebar({ open, onOpenChange }: DocumentsSidebarProps)
 					loadingMore={loadingMore}
 					onLoadMore={onLoadMore}
 					isSearchMode={isSearchMode}
+					mentionedDocIds={mentionedDocIds}
+					onToggleChatMention={handleToggleChatMention}
 				/>
 			</div>
 		</>
diff --git a/surfsense_web/components/ui/tooltip.tsx b/surfsense_web/components/ui/tooltip.tsx
index de59a21be..c19ce6f82 100644
--- a/surfsense_web/components/ui/tooltip.tsx
+++ b/surfsense_web/components/ui/tooltip.tsx
@@ -44,7 +44,7 @@ function TooltipContent({
 				data-slot="tooltip-content"
 				sideOffset={sideOffset}
 				className={cn(
-					"bg-black text-white font-medium shadow-xl px-3 py-1.5 dark:bg-zinc-800 dark:text-zinc-50 border-none animate-in fade-in-0 zoom-in-95 data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=closed]:zoom-out-95 data-[side=bottom]:slide-in-from-top-2 data-[side=left]:slide-in-from-right-2 data-[side=right]:slide-in-from-left-2 data-[side=top]:slide-in-from-bottom-2 z-50 w-fit rounded-md text-xs text-balance pointer-events-none",
+					"bg-black text-white font-medium shadow-xl px-3 py-1.5 dark:bg-zinc-800 dark:text-zinc-50 border-none animate-in fade-in-0 zoom-in-95 data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=closed]:zoom-out-95 data-[side=bottom]:slide-in-from-top-2 data-[side=left]:slide-in-from-right-2 data-[side=right]:slide-in-from-left-2 data-[side=top]:slide-in-from-bottom-2 z-50 w-fit rounded-md text-xs text-balance pointer-events-none select-none",
 					className
 				)}
 				{...props}