diff --git a/packages/api/src/entity/library_item.ts b/packages/api/src/entity/library_item.ts
index f5c15d42e..f127f52b5 100644
--- a/packages/api/src/entity/library_item.ts
+++ b/packages/api/src/entity/library_item.ts
@@ -198,4 +198,10 @@ export class LibraryItem {
 
   @Column('text')
   folder!: string
+
+  @Column('text')
+  labelNames?: string[]
+
+  @Column('text')
+  highlightAnnotations?: string[]
 }
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/labels.ts b/packages/api/src/services/labels.ts
index 33206093d..1bf770a6d 100644
--- a/packages/api/src/services/labels.ts
+++ b/packages/api/src/services/labels.ts
@@ -58,6 +58,32 @@ export const findOrCreateLabels = async (
   )
 }
 
+export const createAndAddLabelsToLibraryItem = async (
+  libraryItemId: string,
+  userId: string,
+  labels?: CreateLabelInput[] | null,
+  rssFeedUrl?: string | null,
+  source?: LabelSource
+) => {
+  if (rssFeedUrl) {
+    // add rss label to labels
+    labels = (labels || []).concat({ name: 'RSS' })
+    source = 'system'
+  }
+
+  // save labels in item
+  if (labels && labels.length > 0) {
+    const newLabels = await findOrCreateLabels(labels, userId)
+
+    await addLabelsToLibraryItem(
+      newLabels.map((l) => l.id),
+      libraryItemId,
+      userId,
+      source
+    )
+  }
+}
+
 export const createAndSaveLabelsInLibraryItem = async (
   libraryItemId: string,
   userId: string,
diff --git a/packages/api/src/services/library_item.ts b/packages/api/src/services/library_item.ts
index 20b47afb7..37422d920 100644
--- a/packages/api/src/services/library_item.ts
+++ b/packages/api/src/services/library_item.ts
@@ -8,6 +8,7 @@ import {
 } from 'typeorm'
 import { QueryDeepPartialEntity } from 'typeorm/query-builder/QueryPartialEntity'
 import { ReadingProgressDataSource } from '../datasources/reading_progress_data_source'
+import { EntityLabel } from '../entity/entity_label'
 import { Highlight } from '../entity/highlight'
 import { Label } from '../entity/label'
 import { LibraryItem, LibraryItemState } from '../entity/library_item'
@@ -18,6 +19,7 @@ import { authTrx, getColumns, queryBuilderToRawSql } from '../repository'
 import { libraryItemRepository } from '../repository/library_item'
 import { Merge } from '../util'
 import { setRecentlySavedItemInRedis } from '../utils/helpers'
+import { logger } from '../utils/logger'
 import { parseSearchQuery } from '../utils/search'
 import { addLabelsToLibraryItem } from './labels'
 
@@ -708,6 +710,32 @@ 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(),
+      })
+
+      return itemRepo.findOneByOrFail({ id })
+    },
+    undefined,
+    userId
+  )
+
+  await pubsub.entityDeleted(EntityType.PAGE, id, userId)
+
+  return deletedLibraryItem
+}
+
 export const updateLibraryItem = async (
   id: string,
   libraryItem: QueryDeepPartialEntity<LibraryItem>,
@@ -719,14 +747,11 @@ export const updateLibraryItem = async (
     async (tx) => {
       const itemRepo = tx.withRepository(libraryItemRepository)
 
-      // reset deletedAt and archivedAt
+      // reset archivedAt
       switch (libraryItem.state) {
         case LibraryItemState.Archived:
           libraryItem.archivedAt = new Date()
           break
-        case LibraryItemState.Deleted:
-          libraryItem.deletedAt = new Date()
-          break
         case LibraryItemState.Processing:
         case LibraryItemState.Succeeded:
           libraryItem.archivedAt = null
@@ -847,15 +872,39 @@ export const createOrUpdateLibraryItem = async (
       )
 
       if (existingLibraryItem) {
+        const id = existingLibraryItem.id
+
+        try {
+          // delete labels and highlights if the item was deleted
+          if (existingLibraryItem.state === LibraryItemState.Deleted) {
+            logger.info('Deleting labels and highlights for item', {
+              id,
+            })
+            await tx.getRepository(Highlight).delete({
+              libraryItem: { id: existingLibraryItem.id },
+            })
+
+            await tx.getRepository(EntityLabel).delete({
+              libraryItemId: existingLibraryItem.id,
+            })
+
+            libraryItem.labelNames = []
+            libraryItem.highlightAnnotations = []
+          }
+        } catch (error) {
+          // continue to save the item even if we failed to delete labels and highlights
+          logger.error('Failed to delete labels and highlights', error)
+        }
+
         // update existing library item
         const newItem = await repo.save({
           ...libraryItem,
-          id: existingLibraryItem.id,
+          id,
           slug: existingLibraryItem.slug, // keep the original slug
         })
 
         // delete the new item if it's different from the existing one
-        if (libraryItem.id && libraryItem.id !== existingLibraryItem.id) {
+        if (libraryItem.id && libraryItem.id !== id) {
           await repo.delete(libraryItem.id)
         }
 
diff --git a/packages/api/src/services/save_page.ts b/packages/api/src/services/save_page.ts
index e4f065e94..f79b28b52 100644
--- a/packages/api/src/services/save_page.ts
+++ b/packages/api/src/services/save_page.ts
@@ -24,7 +24,7 @@ import { parsePreparedContent } from '../utils/parser'
 import { contentReaderForLibraryItem } from '../utils/uploads'
 import { createPageSaveRequest } from './create_page_save_request'
 import { createHighlight } from './highlights'
-import { createAndSaveLabelsInLibraryItem } from './labels'
+import { createAndAddLabelsToLibraryItem } from './labels'
 import { createOrUpdateLibraryItem } from './library_item'
 
 // where we can use APIs to fetch their underlying content.
@@ -132,7 +132,8 @@ export const savePage = async (
   )
   clientRequestId = newItem.id
 
-  await createAndSaveLabelsInLibraryItem(
+  // merge labels
+  await createAndAddLabelsToLibraryItem(
     clientRequestId,
     user.id,
     input.labels,
@@ -157,6 +158,7 @@ export const savePage = async (
       libraryItem: { id: clientRequestId },
     }
 
+    // merge highlights
     try {
       await createHighlight(highlight, clientRequestId, user.id)
     } catch (error) {
@@ -214,7 +216,7 @@ export const parsedContentToLibraryItem = ({
   rssFeedUrl?: string | null
   folder?: string | null
 }): DeepPartial<LibraryItem> & { originalUrl: string } => {
-  logger.info('save_page: state', { url, state, itemId })
+  logger.info('save_page', { url, state, itemId })
   return {
     id: itemId || undefined,
     slug,
@@ -254,5 +256,6 @@ export const parsedContentToLibraryItem = ({
     folder: folder || 'inbox',
     archivedAt:
       state === ArticleSavingRequestStatus.Archived ? new Date() : null,
+    deletedAt: state === ArticleSavingRequestStatus.Deleted ? new Date() : null,
   }
 }
diff --git a/packages/api/test/resolvers/article.test.ts b/packages/api/test/resolvers/article.test.ts
index c93a388b3..27bbf7818 100644
--- a/packages/api/test/resolvers/article.test.ts
+++ b/packages/api/test/resolvers/article.test.ts
@@ -23,16 +23,17 @@ import { getRepository } from '../../src/repository'
 import { createGroup, deleteGroup } from '../../src/services/groups'
 import { createLabel, deleteLabels } from '../../src/services/labels'
 import {
-  createOrUpdateLibraryItem,
   createLibraryItems,
+  createOrUpdateLibraryItem,
+  CreateOrUpdateLibraryItemArgs,
   deleteLibraryItemById,
   deleteLibraryItemByUrl,
   deleteLibraryItems,
   deleteLibraryItemsByUserId,
   findLibraryItemById,
   findLibraryItemByUrl,
+  softDeleteLibraryItem,
   updateLibraryItem,
-  CreateOrUpdateLibraryItemArgs,
 } from '../../src/services/library_item'
 import { deleteUser } from '../../src/services/user'
 import * as createTask from '../../src/utils/createTask'
@@ -712,7 +713,7 @@ describe('Article API', () => {
       await deleteLibraryItemById(itemId, user.id)
     })
 
-    it('marks an article as deleted', async () => {
+    it('soft deletes the item', async () => {
       await graphqlRequest(setBookmarkQuery(itemId, false), authToken).expect(
         200
       )
@@ -2062,11 +2063,8 @@ 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])
       }
     })