diff --git a/packages/convex/filesystem.ts b/packages/convex/filesystem.ts
index 4681183..70e773e 100644
--- a/packages/convex/filesystem.ts
+++ b/packages/convex/filesystem.ts
@@ -128,6 +128,12 @@ export const permanentlyDeleteItems = authenticatedMutation({
 	},
 })
 
+export const emptyTrash = authenticatedMutation({
+	handler: async (ctx) => {
+		return await FileSystem.emptyTrash(ctx)
+	},
+})
+
 export const restoreItems = authenticatedMutation({
 	args: {
 		handles: v.array(VFileSystemHandle),
diff --git a/packages/convex/model/error.ts b/packages/convex/model/error.ts
index c67ef2e..0a0c2da 100644
--- a/packages/convex/model/error.ts
+++ b/packages/convex/model/error.ts
@@ -8,6 +8,7 @@ export enum Code {
 	FileNotFound = "FileNotFound",
 	Internal = "Internal",
 	Unauthenticated = "Unauthenticated",
+	NotFound = "NotFound",
 }
 
 export type ApplicationErrorData = { code: Code; message?: string }
diff --git a/packages/convex/model/filesystem.ts b/packages/convex/model/filesystem.ts
index da3c8b6..f4f33f9 100644
--- a/packages/convex/model/filesystem.ts
+++ b/packages/convex/model/filesystem.ts
@@ -1,6 +1,9 @@
 import { v } from "convex/values"
 import type { Doc, Id } from "../_generated/dataModel"
-import type { AuthenticatedMutationCtx } from "../functions"
+import type {
+	AuthenticatedMutationCtx,
+	AuthenticatedQueryCtx,
+} from "../functions"
 import * as Directories from "./directories"
 import * as Err from "./error"
 import * as Files from "./files"
@@ -47,6 +50,14 @@ export type FileHandle = {
 }
 export type FileSystemHandle = DirectoryHandle | FileHandle
 
+export type DeleteResult = {
+	deleted: {
+		files: number
+		directories: number
+	}
+	errors: Err.ApplicationErrorData[]
+}
+
 export function newFileSystemHandle(item: FileSystemItem): FileSystemHandle {
 	console.log("item", item)
 	switch (item.kind) {
@@ -82,15 +93,21 @@ export const VFileHandle = v.object({
 })
 export const VFileSystemHandle = v.union(VFileHandle, VDirectoryHandle)
 
-export async function ensureRootDirectory(
-	ctx: AuthenticatedMutationCtx,
-): Promise<Id<"directories">> {
-	const existing = await ctx.db
+export async function queryRootDirectory(
+	ctx: AuthenticatedQueryCtx,
+): Promise<Doc<"directories"> | null> {
+	return await ctx.db
 		.query("directories")
 		.withIndex("byParentId", (q) =>
 			q.eq("userId", ctx.user._id).eq("parentId", undefined),
 		)
 		.first()
+}
+
+export async function ensureRootDirectory(
+	ctx: AuthenticatedMutationCtx,
+): Promise<Id<"directories">> {
+	const existing = await queryRootDirectory(ctx)
 
 	if (existing) {
 		return existing._id
@@ -207,7 +224,7 @@ export async function restoreItems(
 export async function deleteItemsPermanently(
 	ctx: AuthenticatedMutationCtx,
 	{ handles }: { handles: FileSystemHandle[] },
-) {
+): Promise<DeleteResult> {
 	// Collect all items to delete (including nested items)
 	const {
 		fileHandles: fileHandlesToDelete,
@@ -232,3 +249,49 @@ export async function deleteItemsPermanently(
 		],
 	}
 }
+
+export async function emptyTrash(
+	ctx: AuthenticatedMutationCtx,
+): Promise<DeleteResult> {
+	const rootDir = await queryRootDirectory(ctx)
+	if (!rootDir) {
+		throw Err.create(Err.Code.NotFound, "user root directory not found")
+	}
+
+	const dirs = await ctx.db
+		.query("directories")
+		.withIndex("byParentId", (q) =>
+			q
+				.eq("userId", ctx.user._id)
+				.eq("parentId", rootDir._id)
+				.gte("deletedAt", 0),
+		)
+		.collect()
+
+	const files = await ctx.db
+		.query("files")
+		.withIndex("byDirectoryId", (q) =>
+			q
+				.eq("userId", ctx.user._id)
+				.eq("directoryId", rootDir._id)
+				.gte("deletedAt", 0),
+		)
+		.collect()
+
+	if (dirs.length === 0 && files.length === 0) {
+		return {
+			deleted: {
+				files: 0,
+				directories: 0,
+			},
+			errors: [],
+		}
+	}
+
+	return await deleteItemsPermanently(ctx, {
+		handles: [
+			...dirs.map((it) => newDirectoryHandle(it._id)),
+			...files.map((it) => newFileHandle(it._id)),
+		],
+	})
+}
diff --git a/packages/web/src/routes/_authenticated/_sidebar-layout/trash.directories.$directoryId.tsx b/packages/web/src/routes/_authenticated/_sidebar-layout/trash.directories.$directoryId.tsx
index 6668720..58155ab 100644
--- a/packages/web/src/routes/_authenticated/_sidebar-layout/trash.directories.$directoryId.tsx
+++ b/packages/web/src/routes/_authenticated/_sidebar-layout/trash.directories.$directoryId.tsx
@@ -2,6 +2,7 @@ import { api } from "@fileone/convex/_generated/api"
 import type { Doc, Id } from "@fileone/convex/_generated/dataModel"
 import {
 	type FileSystemItem,
+	FileType,
 	newFileSystemHandle,
 } from "@fileone/convex/model/filesystem"
 import { useMutation } from "@tanstack/react-query"
@@ -13,7 +14,7 @@ import {
 } from "convex/react"
 import { atom, useAtom, useSetAtom, useStore } from "jotai"
 import { ShredderIcon, TrashIcon, UndoIcon } from "lucide-react"
-import { useCallback, useEffect } from "react"
+import { useCallback, useContext, useEffect } from "react"
 import { toast } from "sonner"
 import { Button } from "@/components/ui/button"
 import {
@@ -45,9 +46,14 @@ export const Route = createFileRoute(
 	component: RouteComponent,
 })
 
+enum ActiveDialogKind {
+	DeleteConfirmation = "DeleteConfirmation",
+	EmptyTrashConfirmation = "EmptyTrashConfirmation",
+}
+
 const contextMenuTargetItemsAtom = atom<FileSystemItem[]>([])
 const fileDragInfoAtom = atom<FileDragInfo | null>(null)
-const isDeleteConfirmationDialogOpenAtom = atom(false)
+const activeDialogAtom = atom<ActiveDialogKind | null>(null)
 const openedFileAtom = atom<Doc<"files"> | null>(null)
 const optimisticRemovedItemsAtom = atom(
 	new Set<Id<"files"> | Id<"directories">>(),
@@ -124,6 +130,7 @@ function RouteComponent() {
 			</TableContextMenu>
 
 			<DeleteConfirmationDialog />
+			<EmptyTrashConfirmationDialog />
 
 			<WithAtom atom={openedFileAtom}>
 				{(openedFile, setOpenedFile) => {
@@ -141,9 +148,7 @@ function RouteComponent() {
 }
 
 function TableContextMenu({ children }: React.PropsWithChildren) {
-	const setIsDeleteConfirmationDialogOpen = useSetAtom(
-		isDeleteConfirmationDialogOpenAtom,
-	)
+	const setActiveDialog = useSetAtom(activeDialogAtom)
 
 	return (
 		<ContextMenu>
@@ -153,7 +158,7 @@ function TableContextMenu({ children }: React.PropsWithChildren) {
 				<ContextMenuItem
 					variant="destructive"
 					onClick={() => {
-						setIsDeleteConfirmationDialogOpen(true)
+						setActiveDialog(ActiveDialogKind.DeleteConfirmation)
 					}}
 				>
 					<ShredderIcon />
@@ -223,9 +228,7 @@ function RestoreContextMenuItem() {
 }
 
 function EmptyTrashButton() {
-	const setIsDeleteConfirmationDialogOpen = useSetAtom(
-		isDeleteConfirmationDialogOpenAtom,
-	)
+	const setActiveDialog = useSetAtom(activeDialogAtom)
 
 	return (
 		<Button
@@ -233,19 +236,19 @@ function EmptyTrashButton() {
 			type="button"
 			variant="destructive"
 			onClick={() => {
-				setIsDeleteConfirmationDialogOpen(true)
+				setActiveDialog(ActiveDialogKind.EmptyTrashConfirmation)
 			}}
 		>
 			<TrashIcon className="size-4" />
-			Empty Trash
+			Empty trash
 		</Button>
 	)
 }
 
 function DeleteConfirmationDialog() {
+	const { rootDirectory } = useContext(DirectoryPageContext)
+	const [activeDialog, setActiveDialog] = useAtom(activeDialogAtom)
 	const [targetItems, setTargetItems] = useAtom(contextMenuTargetItemsAtom)
-	const [isDeleteConfirmationDialogOpen, setIsDeleteConfirmationDialogOpen] =
-		useAtom(isDeleteConfirmationDialogOpenAtom)
 	const setOptimisticRemovedItems = useSetAtom(optimisticRemovedItemsAtom)
 
 	const deletePermanentlyMutation = useConvexMutation(
@@ -276,21 +279,37 @@ function DeleteConfirmationDialog() {
 					`Deleted ${deleted.files} files and ${deleted.directories} directories; failed to delete ${errors.length} items`,
 				)
 			}
-			setIsDeleteConfirmationDialogOpen(false)
+			setActiveDialog(null)
 			setTargetItems([])
 		},
 	})
 
+	const onOpenChange = (open: boolean) => {
+		if (open) {
+			setActiveDialog(ActiveDialogKind.DeleteConfirmation)
+		} else {
+			setActiveDialog(null)
+		}
+	}
+
 	const confirmDelete = () => {
 		deletePermanently({
-			handles: targetItems.map(newFileSystemHandle),
+			handles:
+				targetItems.length > 0
+					? targetItems.map(newFileSystemHandle)
+					: [
+							newFileSystemHandle({
+								kind: FileType.Directory,
+								doc: rootDirectory,
+							}),
+						],
 		})
 	}
 
 	return (
 		<Dialog
-			open={isDeleteConfirmationDialogOpen}
-			onOpenChange={setIsDeleteConfirmationDialogOpen}
+			open={activeDialog === ActiveDialogKind.DeleteConfirmation}
+			onOpenChange={onOpenChange}
 		>
 			<DialogContent>
 				<DialogHeader>
@@ -323,3 +342,61 @@ function DeleteConfirmationDialog() {
 		</Dialog>
 	)
 }
+
+function EmptyTrashConfirmationDialog() {
+	const [activeDialog, setActiveDialog] = useAtom(activeDialogAtom)
+
+	const { mutate: emptyTrash, isPending: isEmptying } = useMutation({
+		mutationFn: useConvexMutation(api.filesystem.emptyTrash),
+		onSuccess: () => {
+			toast.success("Trash emptied successfully")
+			setActiveDialog(null)
+		},
+	})
+
+	function onOpenChange(open: boolean) {
+		if (open) {
+			setActiveDialog(ActiveDialogKind.EmptyTrashConfirmation)
+		} else {
+			setActiveDialog(null)
+		}
+	}
+
+	function confirmEmpty() {
+		emptyTrash(undefined)
+	}
+
+	return (
+		<Dialog
+			open={activeDialog === ActiveDialogKind.EmptyTrashConfirmation}
+			onOpenChange={onOpenChange}
+		>
+			<DialogContent>
+				<DialogHeader>
+					<DialogTitle>Empty your trash?</DialogTitle>
+				</DialogHeader>
+
+				<p>
+					All items in the trash will be permanently deleted. They
+					will be IRRECOVERABLE.
+				</p>
+
+				<DialogFooter>
+					<DialogClose asChild>
+						<Button variant="outline" disabled={isEmptying}>
+							No, go back
+						</Button>
+					</DialogClose>
+					<Button
+						variant="destructive"
+						onClick={confirmEmpty}
+						disabled={isEmptying}
+						loading={isEmptying}
+					>
+						Yes, empty trash
+					</Button>
+				</DialogFooter>
+			</DialogContent>
+		</Dialog>
+	)
+}