diff --git a/packages/api/src/resolvers/article/index.ts b/packages/api/src/resolvers/article/index.ts
index 34c7abdd6..363f97f13 100644
--- a/packages/api/src/resolvers/article/index.ts
+++ b/packages/api/src/resolvers/article/index.ts
@@ -76,6 +76,7 @@ import {
   createOrUpdateLibraryItem,
   findLibraryItemsByPrefix,
   searchLibraryItems,
+  softDeleteLibraryItem,
   sortParamsToSort,
   updateLibraryItem,
   updateLibraryItemReadingProgress,
@@ -532,15 +533,7 @@ export const setBookmarkArticleResolver = authorized<
   }
 
   // delete the item and its metadata
-  const deletedLibraryItem = await updateLibraryItem(
-    articleID,
-    {
-      state: LibraryItemState.Deleted,
-      deletedAt: new Date(),
-    },
-    uid,
-    pubsub
-  )
+  const deletedLibraryItem = await softDeleteLibraryItem(articleID, uid, pubsub)
 
   analytics.track({
     userId: uid,
diff --git a/packages/api/src/services/library_item.ts b/packages/api/src/services/library_item.ts
index 20b47afb7..e56f3c9ef 100644
--- a/packages/api/src/services/library_item.ts
+++ b/packages/api/src/services/library_item.ts
@@ -708,6 +708,38 @@ export const restoreLibraryItem = async (
   )
 }
 
+export const softDeleteLibraryItem = async (
+  id: string,
+  userId: string,
+  pubsub = createPubSubClient()
+): Promise<LibraryItem> => {
+  const deletedLibraryItem = await authTrx(
+    async (tx) => {
+      const itemRepo = tx.withRepository(libraryItemRepository)
+
+      // mark item as deleted
+      await itemRepo.update(id, {
+        state: LibraryItemState.Deleted,
+        deletedAt: new Date(),
+      })
+
+      // delete all labels for this item
+      await tx.getRepository(EntityLabel).delete({ libraryItemId: id })
+
+      // delete all highlights for this item
+      await tx.getRepository(Highlight).delete({ libraryItem: { id } })
+
+      return itemRepo.findOneByOrFail({ id })
+    },
+    undefined,
+    userId
+  )
+
+  await pubsub.entityDeleted(EntityType.PAGE, id, userId)
+
+  return deletedLibraryItem
+}
+
 export const updateLibraryItem = async (
   id: string,
   libraryItem: QueryDeepPartialEntity<LibraryItem>,
diff --git a/packages/api/test/resolvers/article.test.ts b/packages/api/test/resolvers/article.test.ts
index c93a388b3..5d38e024d 100644
--- a/packages/api/test/resolvers/article.test.ts
+++ b/packages/api/test/resolvers/article.test.ts
@@ -21,7 +21,6 @@ import {
 } from '../../src/generated/graphql'
 import { getRepository } from '../../src/repository'
 import { createGroup, deleteGroup } from '../../src/services/groups'
-import { createLabel, deleteLabels } from '../../src/services/labels'
 import {
   createOrUpdateLibraryItem,
   createLibraryItems,
@@ -31,8 +30,9 @@ import {
   deleteLibraryItemsByUserId,
   findLibraryItemById,
   findLibraryItemByUrl,
+  softDeleteLibraryItem,
   updateLibraryItem,
-  CreateOrUpdateLibraryItemArgs,
+  CreateOrUpdateLibraryItemArgs,,
 } from '../../src/services/library_item'
 import { deleteUser } from '../../src/services/user'
 import * as createTask from '../../src/utils/createTask'
@@ -43,7 +43,12 @@ import {
   createTestUser,
   saveLabelsInLibraryItem,
 } from '../db'
-import { generateFakeUuid, graphqlRequest, request } from '../util'
+import {
+  generateFakeShortId,
+  generateFakeUuid,
+  graphqlRequest,
+  request,
+} from '../util'
 
 chai.use(chaiString)
 
@@ -706,18 +711,39 @@ describe('Article API', () => {
       }
       const item = await createOrUpdateLibraryItem(itemToSave, user.id)
       itemId = item.id
+
+      await createAndSaveLabelsInLibraryItem(itemId, user.id, [
+        {
+          name: 'test label 2',
+        },
+      ])
+      await createHighlight(
+        {
+          shortId: generateFakeShortId(),
+          user: { id: user.id },
+          quote: 'test quote 2',
+        },
+        itemId,
+        user.id
+      )
     })
 
     after(async () => {
       await deleteLibraryItemById(itemId, user.id)
     })
 
-    it('marks an article as deleted', async () => {
+    it('marks an item as deleted and deletes all the labels and highlights attached to the item', async () => {
       await graphqlRequest(setBookmarkQuery(itemId, false), authToken).expect(
         200
       )
       const item = await findLibraryItemById(itemId, user.id)
       expect(item?.state).to.eql(LibraryItemState.Deleted)
+
+      const labels = await findLabelsByLibraryItemId(itemId, user.id)
+      expect(labels).to.be.empty
+
+      const highlights = await findHighlightsByLibraryItemId(itemId, user.id)
+      expect(highlights).to.be.empty
     })
   })
 
@@ -2062,11 +2088,8 @@ describe('Article API', () => {
 
       // Delete some items
       for (let i = 0; i < 3; i++) {
-        await updateLibraryItem(
-          items[i].id,
-          { state: LibraryItemState.Deleted, deletedAt: new Date() },
-          user.id
-        )
+        await softDeleteLibraryItem(items[i].id, user.id)
+
         deletedItems.push(items[i])
       }
     })