diff --git a/apps/drive-web/src/files/file-grid.tsx b/apps/drive-web/src/files/file-grid.tsx
index 13a9666..81fc0ce 100644
--- a/apps/drive-web/src/files/file-grid.tsx
+++ b/apps/drive-web/src/files/file-grid.tsx
@@ -1,19 +1,84 @@
-import type { Doc } from "@fileone/convex/dataModel"
-import { TextFileIcon } from "../components/icons/text-file-icon"
-import { MiddleTruncatedText } from "../components/ui/middle-truncated-text"
+import type { Doc, Id } from "@fileone/convex/dataModel"
+import { memo, useCallback } from "react"
+import { TextFileIcon } from "@/components/icons/text-file-icon"
+import { MiddleTruncatedText } from "@/components/ui/middle-truncated-text"
+import { cn } from "@/lib/utils"
+
+export type FileGridSelection = Set<Id<"files">>
+
+export function FileGrid({
+	files,
+	selectedFiles = new Set(),
+	onSelectionChange,
+	onContextMenu,
+}: {
+	files: Doc<"files">[]
+	selectedFiles?: FileGridSelection
+	onSelectionChange?: (selection: FileGridSelection) => void
+	onContextMenu?: (file: Doc<"files">, event: React.MouseEvent) => void
+}) {
+	const onItemSelect = useCallback(
+		(file: Doc<"files">) => {
+			onSelectionChange?.(new Set([file._id]))
+		},
+		[onSelectionChange],
+	)
+
+	const onItemContextMenu = useCallback(
+		(file: Doc<"files">, event: React.MouseEvent) => {
+			onContextMenu?.(file, event)
+			onSelectionChange?.(new Set([file._id]))
+		},
+		[onContextMenu, onSelectionChange],
+	)
 
-export function FileGrid({ files }: { files: Doc<"files">[] }) {
 	return (
-		<div className="grid auto-cols-max grid-flow-col gap-4">
+		<div className="grid auto-cols-max grid-flow-col gap-3">
 			{files.map((file) => (
-				<div
+				<FileGridItem
+					selected={selectedFiles.has(file._id)}
 					key={file._id}
-					className="flex flex-col gap-2 items-center justify-center w-24"
-				>
-					<TextFileIcon className="size-10" />
-					<MiddleTruncatedText>{file.name}</MiddleTruncatedText>
-				</div>
+					file={file}
+					onSelect={onItemSelect}
+					onContextMenu={onItemContextMenu}
+				/>
 			))}
 		</div>
 	)
 }
+
+const FileGridItem = memo(function FileGridItem({
+	selected,
+	file,
+	onSelect,
+	onContextMenu,
+}: {
+	selected: boolean
+	file: Doc<"files">
+	onSelect?: (file: Doc<"files">) => void
+	onContextMenu?: (file: Doc<"files">, event: React.MouseEvent) => void
+}) {
+	return (
+		<button
+			type="button"
+			key={file._id}
+			className={cn(
+				"flex flex-col gap-2 items-center justify-center w-24 p-[calc(var(--spacing)*1+1px)] rounded-md",
+				{ "bg-muted border border-border p-1": selected },
+			)}
+			onClick={() => {
+				onSelect?.(file)
+			}}
+			onContextMenu={(event) => {
+				onContextMenu?.(file, event)
+			}}
+		>
+			<TextFileIcon className="size-10" />
+			<MiddleTruncatedText className="text-sm">
+				{file.name}
+			</MiddleTruncatedText>
+		</button>
+	)
+})
+
+export { FileGridItem }
diff --git a/apps/drive-web/src/routes/_authenticated/_sidebar-layout/recent.tsx b/apps/drive-web/src/routes/_authenticated/_sidebar-layout/recent.tsx
index 012ab84..fa1d528 100644
--- a/apps/drive-web/src/routes/_authenticated/_sidebar-layout/recent.tsx
+++ b/apps/drive-web/src/routes/_authenticated/_sidebar-layout/recent.tsx
@@ -1,22 +1,119 @@
 import { api } from "@fileone/convex/api"
-import { createFileRoute } from "@tanstack/react-router"
-import { useQuery as useConvexQuery } from "convex/react"
+import type { Doc } from "@fileone/convex/dataModel"
+import { newFileHandle } from "@fileone/convex/filesystem"
+import { useMutation } from "@tanstack/react-query"
+import { createFileRoute, Link } from "@tanstack/react-router"
+import {
+	useMutation as useConvexMutation,
+	useQuery as useConvexQuery,
+} from "convex/react"
+import { atom, useAtom, useAtomValue, useSetAtom } from "jotai"
+import { FolderInputIcon, TrashIcon } from "lucide-react"
+import { useCallback } from "react"
+import { toast } from "sonner"
+import {
+	ContextMenu,
+	ContextMenuContent,
+	ContextMenuItem,
+	ContextMenuTrigger,
+} from "@/components/ui/context-menu"
+import { backgroundTaskProgressAtom } from "@/dashboard/state"
+import type { FileGridSelection } from "@/files/file-grid"
 import { FileGrid } from "@/files/file-grid"
+import { formatError } from "@/lib/error"
 
 export const Route = createFileRoute("/_authenticated/_sidebar-layout/recent")({
 	component: RouteComponent,
 })
 
+const selectedFilesAtom = atom(new Set() as FileGridSelection)
+const contextMenuTargetItem = atom<Doc<"files"> | null>(null)
+
 function RouteComponent() {
-	const recentFiles = useConvexQuery(api.filesystem.fetchRecentFiles, {
-		limit: 100,
-	})
-
-	console.log("recentFiles", recentFiles)
-
 	return (
 		<main className="p-4">
-			<FileGrid files={recentFiles ?? []} />
+			<RecentFilesContextMenu>
+				<RecentFilesGrid />
+			</RecentFilesContextMenu>
 		</main>
 	)
 }
+
+function RecentFilesGrid() {
+	const recentFiles = useConvexQuery(api.filesystem.fetchRecentFiles, {
+		limit: 100,
+	})
+	const [selectedFiles, setSelectedFiles] = useAtom(selectedFilesAtom)
+	const setContextMenuTargetItem = useSetAtom(contextMenuTargetItem)
+
+	const handleContextMenu = useCallback(
+		(file: Doc<"files">, _event: React.MouseEvent) => {
+			setContextMenuTargetItem(file)
+		},
+		[setContextMenuTargetItem],
+	)
+
+	return (
+		<FileGrid
+			files={recentFiles ?? []}
+			selectedFiles={selectedFiles}
+			onSelectionChange={setSelectedFiles}
+			onContextMenu={handleContextMenu}
+		/>
+	)
+}
+
+function RecentFilesContextMenu({ children }: { children: React.ReactNode }) {
+	const targetItem = useAtomValue(contextMenuTargetItem)
+	const setBackgroundTaskProgress = useSetAtom(backgroundTaskProgressAtom)
+
+	const { mutate: moveToTrash } = useMutation({
+		mutationFn: useConvexMutation(api.filesystem.moveToTrash),
+		onMutate: () => {
+			setBackgroundTaskProgress({
+				label: "Moving to trash…",
+			})
+		},
+		onSuccess: () => {
+			setBackgroundTaskProgress(null)
+			toast.success("Moved to trash")
+		},
+		onError: (error) => {
+			toast.error("Failed to move to trash", {
+				description: formatError(error),
+			})
+		},
+	})
+
+	return (
+		<ContextMenu>
+			<ContextMenuTrigger asChild>
+				<div>{children}</div>
+			</ContextMenuTrigger>
+			{targetItem && (
+				<ContextMenuContent>
+					<ContextMenuItem>
+						<Link
+							to={`/directories/${targetItem.directoryId}`}
+							className="flex flex-row items-center gap-2"
+						>
+							<FolderInputIcon />
+							Open in directory
+						</Link>
+					</ContextMenuItem>
+					<ContextMenuItem
+						variant="destructive"
+						onClick={() => {
+							moveToTrash({
+								handles: [newFileHandle(targetItem._id)],
+							})
+						}}
+					>
+						<TrashIcon />
+						Move to trash
+					</ContextMenuItem>
+				</ContextMenuContent>
+			)}
+		</ContextMenu>
+	)
+}