diff --git a/packages/api/src/services/labels.ts b/packages/api/src/services/labels.ts
index d4d1aff16..8ad7c24a6 100644
--- a/packages/api/src/services/labels.ts
+++ b/packages/api/src/services/labels.ts
@@ -1,6 +1,7 @@
 import { DeepPartial, FindOptionsWhere, In } from 'typeorm'
 import { QueryDeepPartialEntity } from 'typeorm/query-builder/QueryPartialEntity'
 import { EntityLabel, LabelSource } from '../entity/entity_label'
+import { Highlight } from '../entity/highlight'
 import { Label } from '../entity/label'
 import { createPubSubClient, EntityType, PubsubClient } from '../pubsub'
 import { authTrx } from '../repository'
@@ -187,6 +188,20 @@ export const saveLabelsInHighlight = async (
     { highlightId, labels },
     userId
   )
+
+  const highlight = await authTrx(async (tx) =>
+    tx.getRepository(Highlight).findOne({
+      where: { id: highlightId },
+      relations: ['libraryItem'],
+    })
+  )
+  if (highlight) {
+    // update labels in library item
+    const jobs = await bulkEnqueueUpdateLabels([
+      { libraryItemId: highlight.libraryItem.id, userId },
+    ])
+    logger.info('update labels jobs enqueued', jobs)
+  }
 }
 
 export const findLabelsByIds = async (
diff --git a/packages/api/src/services/library_item.ts b/packages/api/src/services/library_item.ts
index 0f3906e63..7151c8d2b 100644
--- a/packages/api/src/services/library_item.ts
+++ b/packages/api/src/services/library_item.ts
@@ -17,6 +17,7 @@ import {
   valuesToRawSql,
 } from '../repository'
 import { libraryItemRepository } from '../repository/library_item'
+import { bulkEnqueueUpdateLabels } from '../utils/createTask'
 import { setRecentlySavedItemInRedis, wordsCount } from '../utils/helpers'
 import { logger } from '../utils/logger'
 import { parseSearchQuery } from '../utils/search'
@@ -1020,7 +1021,17 @@ export const batchUpdateLibraryItems = async (
             return !existingLabel
           })
       )
-      return tx.getRepository(EntityLabel).save(labelsToAdd)
+      const labelsAdded = await tx.getRepository(EntityLabel).save(labelsToAdd)
+
+      const data = labelsAdded.map((label) => ({
+        libraryItemId: label.libraryItemId,
+        userId,
+      }))
+      // update labels in library item
+      const jobs = await bulkEnqueueUpdateLabels(data)
+      logger.info('update labels jobs enqueued', jobs)
+
+      return
     }
 
     // generate raw sql because postgres doesn't support prepared statements in DO blocks