diff --git a/packages/api/src/jobs/update_db.ts b/packages/api/src/jobs/update_db.ts
index 03e670b25..3dc7deb8b 100644
--- a/packages/api/src/jobs/update_db.ts
+++ b/packages/api/src/jobs/update_db.ts
@@ -1,6 +1,7 @@
 import { authTrx } from '../repository'
 
 export const UPDATE_LABELS_JOB = 'update-labels'
+export const UPDATE_HIGHLIGHT_JOB = 'update-highlight'
 
 export interface UpdateLabelsData {
   libraryItemId: string
@@ -20,7 +21,31 @@ export const updateLabels = async (data: UpdateLabelsData) => {
         )
         UPDATE omnivore.library_item li
         SET label_names = COALESCE((SELECT names_agg FROM labels_agg), ARRAY[]::TEXT[])
-        WHERE li.id = $1;`,
+        WHERE li.id = $1`,
+        [data.libraryItemId]
+      ),
+    undefined,
+    data.userId
+  )
+}
+
+export interface UpdateHighlightData {
+  libraryItemId: string
+  userId: string
+}
+
+export const updateHighlight = async (data: UpdateHighlightData) => {
+  return authTrx(
+    async (tx) =>
+      tx.query(
+        `WITH highlight_agg AS (
+          SELECT array_agg(COALESCE(annotation, '')) AS annotation_agg
+          FROM omnivore.highlight
+          WHERE library_item_id = $1
+        )
+        UPDATE omnivore.library_item
+        SET highlight_annotations = COALESCE((SELECT annotation_agg FROM highlight_agg), ARRAY[]::TEXT[])
+        WHERE id = $1`,
         [data.libraryItemId]
       ),
     undefined,
diff --git a/packages/api/src/queue-processor.ts b/packages/api/src/queue-processor.ts
index f4458e53e..f80a9d8ce 100644
--- a/packages/api/src/queue-processor.ts
+++ b/packages/api/src/queue-processor.ts
@@ -12,7 +12,12 @@ import { refreshAllFeeds } from './jobs/rss/refreshAllFeeds'
 import { refreshFeed } from './jobs/rss/refreshFeed'
 import { savePageJob } from './jobs/save_page'
 import { triggerRule, TRIGGER_RULE_JOB_NAME } from './jobs/trigger_rule'
-import { updateLabels, UPDATE_LABELS_JOB } from './jobs/update_db'
+import {
+  updateHighlight,
+  updateLabels,
+  UPDATE_HIGHLIGHT_JOB,
+  UPDATE_LABELS_JOB,
+} from './jobs/update_db'
 import { updatePDFContentJob } from './jobs/update_pdf_content'
 import { redisDataSource } from './redis_data_source'
 import { CustomTypeOrmLogger } from './utils/logger'
@@ -128,6 +133,8 @@ const main = async () => {
           return triggerRule(job.data)
         case UPDATE_LABELS_JOB:
           return updateLabels(job.data)
+        case UPDATE_HIGHLIGHT_JOB:
+          return updateHighlight(job.data)
       }
     },
     {
diff --git a/packages/api/src/services/highlights.ts b/packages/api/src/services/highlights.ts
index 2d062418f..509f666b4 100644
--- a/packages/api/src/services/highlights.ts
+++ b/packages/api/src/services/highlights.ts
@@ -8,6 +8,8 @@ import { homePageURL } from '../env'
 import { createPubSubClient, EntityType } from '../pubsub'
 import { authTrx } from '../repository'
 import { highlightRepository } from '../repository/highlight'
+import { enqueueUpdateHighlight } from '../utils/createTask'
+import { logger } from '../utils/logger'
 
 type HighlightEvent = { id: string; pageId: string }
 type CreateHighlightEvent = DeepPartial<Highlight> & HighlightEvent
@@ -61,6 +63,14 @@ export const createHighlight = async (
     userId
   )
 
+  if (newHighlight.annotation) {
+    const job = await enqueueUpdateHighlight({
+      libraryItemId,
+      userId,
+    })
+    logger.info('update highlight job enqueued', job)
+  }
+
   return newHighlight
 }
 
@@ -103,6 +113,14 @@ export const mergeHighlights = async (
     userId
   )
 
+  if (newHighlight.annotation) {
+    const job = await enqueueUpdateHighlight({
+      libraryItemId,
+      userId,
+    })
+    logger.info('update highlight job enqueued', job)
+  }
+
   return newHighlight
 }
 
@@ -125,28 +143,48 @@ export const updateHighlight = async (
     })
   })
 
+  const libraryItemId = updatedHighlight.libraryItem.id
   await pubsub.entityUpdated<UpdateHighlightEvent>(
     EntityType.HIGHLIGHT,
-    { ...highlight, id: highlightId, pageId: updatedHighlight.libraryItem.id },
+    { ...highlight, id: highlightId, pageId: libraryItemId },
     userId
   )
 
+  if (highlight.annotation) {
+    const job = await enqueueUpdateHighlight({
+      libraryItemId,
+      userId,
+    })
+    logger.info('update highlight job enqueued', job)
+  }
+
   return updatedHighlight
 }
 
 export const deleteHighlightById = async (highlightId: string) => {
-  return authTrx(async (tx) => {
+  const deletedHighlight = await authTrx(async (tx) => {
     const highlightRepo = tx.withRepository(highlightRepository)
     const highlight = await highlightRepo.findOneOrFail({
       where: { id: highlightId },
       relations: {
         user: true,
+        libraryItem: true,
       },
     })
 
     await highlightRepo.delete(highlightId)
     return highlight
   })
+
+  if (deletedHighlight.annotation) {
+    const job = await enqueueUpdateHighlight({
+      libraryItemId: deletedHighlight.libraryItem.id,
+      userId: deletedHighlight.user.id,
+    })
+    logger.info('update highlight job enqueued', job)
+  }
+
+  return deletedHighlight
 }
 
 export const findHighlightById = async (
diff --git a/packages/api/src/utils/createTask.ts b/packages/api/src/utils/createTask.ts
index a662262f1..3b845c492 100644
--- a/packages/api/src/utils/createTask.ts
+++ b/packages/api/src/utils/createTask.ts
@@ -17,7 +17,12 @@ import {
 import { THUMBNAIL_JOB } from '../jobs/find_thumbnail'
 import { queueRSSRefreshFeedJob } from '../jobs/rss/refreshAllFeeds'
 import { TriggerRuleJobData, TRIGGER_RULE_JOB_NAME } from '../jobs/trigger_rule'
-import { UpdateLabelsData, UPDATE_LABELS_JOB } from '../jobs/update_db'
+import {
+  UpdateHighlightData,
+  UpdateLabelsData,
+  UPDATE_HIGHLIGHT_JOB,
+  UPDATE_LABELS_JOB,
+} from '../jobs/update_db'
 import { getBackendQueue } from '../queue-processor'
 import { redisDataSource } from '../redis_data_source'
 import { signFeatureToken } from '../services/features'
@@ -682,4 +687,19 @@ export const bulkEnqueueUpdateLabels = async (data: UpdateLabelsData[]) => {
   }
 }
 
+export const enqueueUpdateHighlight = async (data: UpdateHighlightData) => {
+  const queue = await getBackendQueue()
+  if (!queue) {
+    return undefined
+  }
+
+  try {
+    return queue.add(UPDATE_HIGHLIGHT_JOB, data, {
+      priority: 1,
+    })
+  } catch (error) {
+    logger.error('error enqueuing update highlight job', error)
+  }
+}
+
 export default createHttpTaskWithToken