diff --git a/packages/api/src/events/highlight_subscriber.ts b/packages/api/src/events/highlight_subscriber.ts
deleted file mode 100644
index f5725bd3b..000000000
--- a/packages/api/src/events/highlight_subscriber.ts
+++ /dev/null
@@ -1,103 +0,0 @@
-import {
-  EntityManager,
-  EntitySubscriberInterface,
-  EventSubscriber,
-  InsertEvent,
-  ObjectLiteral,
-  RemoveEvent,
-  UpdateEvent,
-} from 'typeorm'
-import { Highlight } from '../entity/highlight'
-import { Label } from '../entity/label'
-import { LibraryItem } from '../entity/library_item'
-import { createPubSubClient, EntityType } from '../pubsub'
-
-@EventSubscriber()
-export class HighlightSubscriber
-  implements EntitySubscriberInterface<Highlight>
-{
-  private readonly pubsubClient = createPubSubClient()
-
-  async updateLibraryItem(manager: EntityManager, libraryItemId: string) {
-    // get all the highlights belonging to the library_item
-    const highlights = await manager.getRepository(Highlight).find({
-      where: { libraryItem: { id: libraryItemId } },
-      relations: {
-        labels: true,
-      },
-    })
-
-    const highlightLabels: string[] = []
-    const highlightAnnotations: string[] = []
-
-    // for each highlight, add the lowercased label names to highlight_labels
-    // and the annotation to highlight_annotations
-    highlights.forEach((highlight) => {
-      highlight.labels &&
-        highlightLabels.push(
-          ...highlight.labels.map((label) => label.name.toLowerCase())
-        )
-      highlightAnnotations.push(highlight.annotation || '')
-    })
-
-    // update highlight_labels and highlight_annotations on library_item
-    await manager.update(LibraryItem, libraryItemId, {
-      highlightAnnotations,
-      highlightLabels,
-    })
-  }
-
-  listenTo() {
-    return Highlight
-  }
-
-  async afterInsert(event: InsertEvent<Highlight>): Promise<void> {
-    await this.updateLibraryItem(event.manager, event.entity.libraryItem.id)
-
-    await this.pubsubClient.entityCreated<Highlight>(
-      EntityType.HIGHLIGHT,
-      event.entity,
-      event.entity.libraryItem.user.id
-    )
-  }
-
-  async afterUpdate(event: UpdateEvent<Highlight>): Promise<void> {
-    if (event.entity) {
-      await this.updateLibraryItem(
-        event.manager,
-        event.databaseEntity.libraryItem.id
-      )
-
-      // publish update event
-      await this.pubsubClient.entityUpdated<ObjectLiteral>(
-        EntityType.HIGHLIGHT,
-        { ...event.entity, libraryItem: event.databaseEntity.libraryItem },
-        event.databaseEntity.libraryItem.user.id
-      )
-
-      // publish label added event if a label was added
-      if (event.entity.labels) {
-        await this.pubsubClient.entityCreated<Label>(
-          EntityType.LABEL,
-          event.entity.labels,
-          event.databaseEntity.libraryItem.user.id
-        )
-      }
-    }
-  }
-
-  async afterRemove(event: RemoveEvent<Highlight>): Promise<void> {
-    if (event.entityId) {
-      await this.updateLibraryItem(
-        event.manager,
-        event.databaseEntity.libraryItem.id
-      )
-
-      await this.pubsubClient.entityDeleted(
-        EntityType.HIGHLIGHT,
-        event.entityId,
-        event.databaseEntity.libraryItem.user.id
-      )
-    }
-  }
-}
diff --git a/packages/api/src/events/library_item_subscriber.ts b/packages/api/src/events/library_item_subscriber.ts
deleted file mode 100644
index 32893f622..000000000
--- a/packages/api/src/events/library_item_subscriber.ts
+++ /dev/null
@@ -1,83 +0,0 @@
-import {
-  EntitySubscriberInterface,
-  EventSubscriber,
-  InsertEvent,
-  ObjectLiteral,
-  UpdateEvent,
-} from 'typeorm'
-import { Label } from '../entity/label'
-import { LibraryItem, LibraryItemState } from '../entity/library_item'
-import { createPubSubClient, EntityType } from '../pubsub'
-
-@EventSubscriber()
-export class LibraryItemSubscriber
-  implements EntitySubscriberInterface<LibraryItem>
-{
-  private readonly pubsubClient = createPubSubClient()
-
-  listenTo() {
-    return LibraryItem
-  }
-
-  async afterInsert(event: InsertEvent<LibraryItem>): Promise<void> {
-    // Only publish the event if the library item has been successfully created
-    if (event.entity.state === LibraryItemState.Succeeded) {
-      await this.pubsubClient.entityCreated<LibraryItem>(
-        EntityType.PAGE,
-        event.entity,
-        event.entity.user.id
-      )
-    }
-  }
-
-  async afterUpdate(event: UpdateEvent<LibraryItem>): Promise<void> {
-    if (event.entity) {
-      // publish delete event if the library item has been deleted
-      if (event.entity.state === LibraryItemState.Deleted) {
-        return this.pubsubClient.entityDeleted(
-          EntityType.PAGE,
-          event.databaseEntity.id,
-          event.databaseEntity.user.id
-        )
-      }
-
-      // publish create event if the library item has finished processing
-      if (
-        event.databaseEntity.state === LibraryItemState.Processing &&
-        event.entity.state === LibraryItemState.Succeeded
-      ) {
-        return this.pubsubClient.entityCreated<LibraryItem>(
-          EntityType.PAGE,
-          {
-            ...event.databaseEntity,
-            ...event.entity,
-          },
-          event.databaseEntity.user.id
-        )
-      }
-
-      // publish update event for all other cases
-      await this.pubsubClient.entityUpdated<ObjectLiteral>(
-        EntityType.PAGE,
-        event.entity,
-        event.databaseEntity.user.id
-      )
-
-      // publish label added event if a label was added
-      if (event.entity.labels) {
-        const labels = event.entity.labels as Label[]
-        await event.manager
-          .getRepository(LibraryItem)
-          .update(event.databaseEntity.id, {
-            labelNames: labels.map((label) => label.name.toLowerCase()),
-          })
-
-        await this.pubsubClient.entityCreated<Label>(
-          EntityType.LABEL,
-          event.entity.labels,
-          event.databaseEntity.user.id
-        )
-      }
-    }
-  }
-}
diff --git a/packages/api/src/repository/api_key.ts b/packages/api/src/repository/api_key.ts
new file mode 100644
index 000000000..335af43d8
--- /dev/null
+++ b/packages/api/src/repository/api_key.ts
@@ -0,0 +1,4 @@
+import { entityManager } from '.'
+import { ApiKey } from '../entity/api_key'
+
+export const apiKeyRepository = entityManager.getRepository(ApiKey)
diff --git a/packages/api/src/repository/index.ts b/packages/api/src/repository/index.ts
index 39eec1566..44d66c9eb 100644
--- a/packages/api/src/repository/index.ts
+++ b/packages/api/src/repository/index.ts
@@ -8,7 +8,6 @@ import { GroupMembership } from '../entity/groups/group_membership'
 import { Invite } from '../entity/groups/invite'
 import { Highlight } from '../entity/highlight'
 import { Integration } from '../entity/integration'
-import { Label } from '../entity/label'
 import { LibraryItem } from '../entity/library_item'
 import { NewsletterEmail } from '../entity/newsletter_email'
 import { Profile } from '../entity/profile'
@@ -19,19 +18,19 @@ import { AbuseReport } from '../entity/reports/abuse_report'
 import { ContentDisplayReport } from '../entity/reports/content_display_report'
 import { Rule } from '../entity/rule'
 import { Subscription } from '../entity/subscription'
-import { UploadFile } from '../entity/upload_file'
 import { UserDeviceToken } from '../entity/user_device_tokens'
 import { UserPersonalization } from '../entity/user_personalization'
 import { Webhook } from '../entity/webhook'
 
 export const setClaims = async (
   manager: EntityManager,
-  uid: string
-): Promise<void> => {
-  const dbRole = 'omnivore_user'
-  return manager
-    .query('SELECT * from omnivore.set_claims($1, $2)', [uid, dbRole])
-    .then()
+  uid = '00000000-0000-0000-0000-000000000000',
+  dbRole = 'omnivore_user'
+): Promise<unknown> => {
+  return manager.query('SELECT * from omnivore.set_claims($1, $2)', [
+    uid,
+    dbRole,
+  ])
 }
 
 export const getRepository = <T>(entity: EntityTarget<T>): Repository<T> => {
@@ -40,7 +39,6 @@ export const getRepository = <T>(entity: EntityTarget<T>): Repository<T> => {
 
 export const entityManager = appDataSource.manager
 
-export const uploadFileRepository = getRepository(UploadFile)
 export const reminderRepository = getRepository(Reminder)
 export const libraryItemRepository = getRepository(LibraryItem)
 export const groupMembershipRepository = getRepository(GroupMembership)
@@ -54,7 +52,6 @@ export const filterRepository = getRepository(Filter)
 export const followerRepository = getRepository(Follower)
 export const highlightRepository = getRepository(Highlight)
 export const integrationRepository = getRepository(Integration)
-export const labelRepository = getRepository(Label)
 export const newsletterEmailRepository = getRepository(NewsletterEmail)
 export const profileRepository = getRepository(Profile)
 export const receivedEmailRepository = getRepository(ReceivedEmail)
diff --git a/packages/api/src/repository/label.ts b/packages/api/src/repository/label.ts
new file mode 100644
index 000000000..d9874087a
--- /dev/null
+++ b/packages/api/src/repository/label.ts
@@ -0,0 +1,88 @@
+import { In } from 'typeorm'
+import { entityManager } from '.'
+import { Label } from '../entity/label'
+import { generateRandomColor } from '../utils/helpers'
+
+const INTERNAL_LABELS_WITH_COLOR = new Map<
+  string,
+  { name: string; color: string }
+>([
+  ['favorites', { name: 'Favorites', color: '#FFD700' }],
+  ['library', { name: 'Library', color: '#584C42' }],
+  ['rss', { name: 'RSS', color: '#F26522' }],
+  ['newsletter', { name: 'Newsletter', color: '#07D2D1' }],
+])
+
+export const getInternalLabelWithColor = (name: string) => {
+  return INTERNAL_LABELS_WITH_COLOR.get(name.toLowerCase())
+}
+
+const isLabelInternal = (name: string): boolean => {
+  return INTERNAL_LABELS_WITH_COLOR.has(name.toLowerCase())
+}
+
+const toPartialLabel = (
+  label: {
+    name: string
+    color?: string | null
+    description?: string | null
+  },
+  userId: string
+) => {
+  return {
+    user: { id: userId },
+    name: label.name,
+    color: label.color || generateRandomColor(), // assign a random color if not provided
+    description: label.description,
+    internal: isLabelInternal(label.name),
+  }
+}
+
+export const labelRepository = entityManager.getRepository(Label).extend({
+  findById(id: string) {
+    return this.findOneBy({ id })
+  },
+
+  findByName(name: string) {
+    return this.createQueryBuilder()
+      .where('LOWER(name) = LOWER(:name)', { name }) // case insensitive
+      .getOne()
+  },
+
+  findByNames(names: string[]) {
+    return this.createQueryBuilder()
+      .where('LOWER(name) IN (:...names)', {
+        names: names.map((n) => n.toLowerCase()),
+      })
+      .getMany()
+  },
+
+  findByIds(labelIds: string[]) {
+    return this.find({
+      where: { id: In(labelIds) },
+      select: ['id', 'name', 'color', 'description', 'createdAt'],
+    })
+  },
+
+  createLabel(
+    label: {
+      name: string
+      color?: string | null
+      description?: string | null
+    },
+    userId: string
+  ) {
+    return this.save(toPartialLabel(label, userId))
+  },
+
+  createLabels(
+    labels: {
+      name: string
+      color?: string | null
+      description?: string | null
+    }[],
+    userId: string
+  ) {
+    return this.save(labels.map((l) => toPartialLabel(l, userId)))
+  },
+})
diff --git a/packages/api/src/repository/upload_file.ts b/packages/api/src/repository/upload_file.ts
new file mode 100644
index 000000000..38e3bd967
--- /dev/null
+++ b/packages/api/src/repository/upload_file.ts
@@ -0,0 +1,4 @@
+import { entityManager } from '.'
+import { UploadFile } from '../entity/upload_file'
+
+export const uploadFileRepository = entityManager.getRepository(UploadFile)
diff --git a/packages/api/src/resolvers/api_key/index.ts b/packages/api/src/resolvers/api_key/index.ts
index 19827c767..4aaf986b4 100644
--- a/packages/api/src/resolvers/api_key/index.ts
+++ b/packages/api/src/resolvers/api_key/index.ts
@@ -20,8 +20,8 @@ import { authorized } from '../../utils/helpers'
 export const apiKeysResolver = authorized<ApiKeysSuccess, ApiKeysError>(
   async (_, __, { log, authTrx }) => {
     try {
-      const apiKeys = await authTrx<Promise<ApiKey[]>>(async (em) => {
-        return em.getRepository(ApiKey).find({
+      const apiKeys = await authTrx<Promise<ApiKey[]>>(async (tx) => {
+        return tx.find(ApiKey, {
           select: ['id', 'name', 'scopes', 'expiresAt', 'createdAt', 'usedAt'],
           order: {
             usedAt: { direction: 'DESC', nulls: 'last' },
@@ -51,8 +51,8 @@ export const generateApiKeyResolver = authorized<
   try {
     const exp = new Date(expiresAt)
     const originalKey = generateApiKey()
-    const apiKeyCreated = await authTrx<Promise<ApiKey>>(async (em) => {
-      return em.getRepository(ApiKey).save({
+    const apiKeyCreated = await authTrx<Promise<ApiKey>>(async (tx) => {
+      return tx.save(ApiKey, {
         user: { id: uid },
         name,
         key: hashApiKey(originalKey),
@@ -89,14 +89,13 @@ export const revokeApiKeyResolver = authorized<
   MutationRevokeApiKeyArgs
 >(async (_, { id }, { claims: { uid }, log, authTrx }) => {
   try {
-    const deletedApiKey = await authTrx<Promise<ApiKey | null>>(async (em) => {
-      const apiKeyRepository = em.getRepository(ApiKey)
-      const apiKey = await apiKeyRepository.findOneBy({ id })
+    const deletedApiKey = await authTrx<Promise<ApiKey | null>>(async (tx) => {
+      const apiKey = await tx.findOneBy(ApiKey, { id })
       if (!apiKey) {
         return null
       }
 
-      return apiKeyRepository.remove(apiKey)
+      return tx.remove(ApiKey, apiKey)
     })
 
     if (!deletedApiKey) {
diff --git a/packages/api/src/resolvers/article/index.ts b/packages/api/src/resolvers/article/index.ts
index b5fe067b5..5a49bff5b 100644
--- a/packages/api/src/resolvers/article/index.ts
+++ b/packages/api/src/resolvers/article/index.ts
@@ -5,7 +5,9 @@
 /* eslint-disable @typescript-eslint/no-floating-promises */
 import { Readability } from '@omnivore/readability'
 import graphqlFields from 'graphql-fields'
+import { Label } from '../../entity/label'
 import { LibraryItemType } from '../../entity/library_item'
+import { UploadFile } from '../../entity/upload_file'
 import { env } from '../../env'
 import {
   Article,
@@ -57,16 +59,15 @@ import {
   UpdateReason,
   UpdatesSinceError,
   UpdatesSinceErrorCode,
-  UpdatesSinceSuccess,
+  UpdatesSinceSuccess
 } from '../../generated/graphql'
-import { uploadFileRepository } from '../../repository'
 import { getLibraryItemByUrl } from '../../repository/library_item'
-import { getUserById, userRepository } from '../../repository/user'
+import { userRepository } from '../../repository/user'
 import { createPageSaveRequest } from '../../services/create_page_save_request'
 import {
   addLabelToPage,
-  createLabels,
-  getLabelsByIds,
+  getLabelsAndCreateIfNotExist,
+  getLabelsByIds
 } from '../../services/labels'
 import { searchLibraryItems } from '../../services/library_item'
 import { setFileUploadComplete } from '../../services/save_file'
@@ -75,7 +76,6 @@ import { traceAs } from '../../tracing'
 import { Merge } from '../../util'
 import { analytics } from '../../utils/analytics'
 import { isSiteBlockedForParse } from '../../utils/blocked'
-import { ContentParseError } from '../../utils/errors'
 import {
   authorized,
   cleanUrl,
@@ -85,7 +85,7 @@ import {
   pageError,
   titleForFilePath,
   userDataToUser,
-  validatedDate,
+  validatedDate
 } from '../../utils/helpers'
 import { createImageProxyUrl } from '../../utils/imageproxy'
 import {
@@ -93,13 +93,13 @@ import {
   getDistillerResult,
   htmlToMarkdown,
   ParsedContentPuppeteer,
-  parsePreparedContent,
+  parsePreparedContent
 } from '../../utils/parser'
 import { parseSearchQuery, SortBy, SortOrder } from '../../utils/search'
 import {
   contentReaderForPage,
   getStorageFileDetails,
-  makeStorageFilePublic,
+  makeStorageFilePublic
 } from '../../utils/uploads'
 import { WithDataSourcesContext } from '../types'
 import { itemTypeForContentType } from '../upload_files'
@@ -231,28 +231,21 @@ export const createArticleResolver = authorized<
       // save state
       const archivedAt =
         state === ArticleSavingRequestStatus.Archived ? new Date() : null
-      // if (pageId) {
-      //   const reminder = await getRepository(Reminder).findOneBy({
-      //     articleSavingRequest: pageId,
-      //     user: { id: uid },
-      //   })
-      //   if (reminder && reminder.archiveUntil) {
-      //     archivedAt = new Date()
-      //   }
-      // }
-      // add labels to page
-      const labels = inputLabels
-        ? await createLabels(ctx, inputLabels)
-        : undefined
+      // save labels
+      let labels: Label[] | undefined = undefined
+      if (inputLabels) {
+        labels = await getLabelsAndCreateIfNotExist(inputLabels, uid)
+      }
 
       if (uploadFileId) {
         /* We do not trust the values from client, lookup upload file by querying
          * with filtering on user ID and URL to verify client's uploadFileId is valid.
          */
-        const uploadFile = await uploadFileRepository.findOneBy({
-          id: uploadFileId,
-          user: { id: uid },
-        })
+        const uploadFile = await authTrx((tx) =>
+          tx.findOneBy(UploadFile, {
+           id: uploadFileId,
+          })
+        )
         if (!uploadFile) {
           return pageError(
             { errorCodes: [CreateArticleErrorCode.UploadFileMissing] },
@@ -293,9 +286,8 @@ export const createArticleResolver = authorized<
         return DUMMY_RESPONSE
       }
 
-      const saveTime = new Date()
       const slug = generateSlug(parsedContent?.title || croppedPathname)
-      const articleToSave = parsedContentToLibraryItem({
+      const libraryItemToSave = parsedContentToLibraryItem({
         url,
         title,
         parsedContent,
@@ -309,11 +301,10 @@ export const createArticleResolver = authorized<
         uploadFileHash,
         canonicalUrl,
         uploadFileId,
-        saveTime,
       })
 
       log.info('New article saving', {
-        parsedArticle: Object.assign({}, articleToSave, {
+        parsedArticle: Object.assign({}, libraryItemToSave, {
           content: undefined,
           originalHtml: undefined,
         }),
@@ -341,17 +332,17 @@ export const createArticleResolver = authorized<
         await makeStorageFilePublic(uploadFileData.id, uploadFileData.fileName)
       }
       // save page's state and labels
-      articleToSave.archivedAt = archivedAt
-      articleToSave.labels = labels
+      libraryItemToSave.archivedAt = archivedAt
+      libraryItemToSave.labels = labels
 
       const existingLibraryItem = await getLibraryItemByUrl(
-        articleToSave.originalUrl!,
+        libraryItemToSave.originalUrl!,
         uid
       )
       pageId = existingLibraryItem?.id || pageId
       if (pageId || existingLibraryItem) {
         // update existing page's state from processing to succeeded
-        const updated = await updatePage(pageId, articleToSave, {
+        const updated = await updatePage(pageId, libraryItemToSave, {
           ...ctx,
           uid,
         })
@@ -367,7 +358,7 @@ export const createArticleResolver = authorized<
         }
       } else {
         // create new page in elastic
-        const newPageId = await createPage(articleToSave, { ...ctx, uid })
+        const newPageId = await createPage(libraryItemToSave, { ...ctx, uid })
         if (!newPageId) {
           return pageError(
             {
@@ -377,39 +368,26 @@ export const createArticleResolver = authorized<
             pageId
           )
         }
-        articleToSave.id = newPageId
+        libraryItemToSave.id = newPageId
       }
       log.info(
         'page created in elastic',
-        articleToSave.id,
-        articleToSave.url,
-        articleToSave.slug,
-        articleToSave.title
+        libraryItemToSave.id,
+        libraryItemToSave.url,
+        libraryItemToSave.slug,
+        libraryItemToSave.title
       )
 
       const createdArticle: PartialArticle = {
-        ...articleToSave,
-        isArchived: !!articleToSave.archivedAt,
+        ...libraryItemToSave,
+        isArchived: !!libraryItemToSave.archivedAt,
       }
       return {
         user,
         created: false,
         createdArticle: createdArticle,
       }
-    } catch (error) {
-      if (
-        error instanceof ContentParseError &&
-        error.message === 'UNABLE_TO_PARSE'
-      ) {
-        return pageError(
-          { errorCodes: [CreateArticleErrorCode.UnableToParse] },
-          ctx,
-          pageId
-        )
-      }
-      throw error
-    }
-  }
+    }  }
 )
 
 export type ArticleSuccessPartial = Merge<
diff --git a/packages/api/src/resolvers/labels/index.ts b/packages/api/src/resolvers/labels/index.ts
index f84942922..d18e8e5a7 100644
--- a/packages/api/src/resolvers/labels/index.ts
+++ b/packages/api/src/resolvers/labels/index.ts
@@ -41,8 +41,8 @@ import { createPubSubClient } from '../../pubsub'
 import { getRepository, setClaims } from '../../repository'
 import {
   createLabel,
-  createLabels,
   getLabelByName,
+  getLabelsAndCreateIfNotExist,
   getLabelsByIds,
 } from '../../services/labels'
 import { analytics } from '../../utils/analytics'
@@ -252,7 +252,7 @@ export const setLabelsResolver = authorized<
     if (labels && labels.length > 0) {
       // for new clients that send label names
       // create labels if they don't exist
-      labelsSet = await createLabels(ctx, labels)
+      labelsSet = await getLabelsAndCreateIfNotExist(ctx, labels)
     } else if (labelIds && labelIds.length > 0) {
       // for old clients that send labelIds
       labelsSet = await getLabelsByIds(uid, labelIds)
@@ -419,7 +419,7 @@ export const setLabelsForHighlightResolver = authorized<
     if (labels && labels.length > 0) {
       // for new clients that send label names
       // create labels if they don't exist
-      labelsSet = await createLabels(ctx, labels)
+      labelsSet = await getLabelsAndCreateIfNotExist(ctx, labels)
     } else if (labelIds && labelIds.length > 0) {
       // for old clients that send labelIds
       labelsSet = await getLabelsByIds(uid, labelIds)
diff --git a/packages/api/src/services/create_page_save_request.ts b/packages/api/src/services/create_page_save_request.ts
index ffc29e1ff..cc1c61c8c 100644
--- a/packages/api/src/services/create_page_save_request.ts
+++ b/packages/api/src/services/create_page_save_request.ts
@@ -94,7 +94,7 @@ export const createPageSaveRequest = async ({
   try {
     validateUrl(url)
   } catch (error) {
-    logger.info('invalid url', url, error)
+    logger.error('invalid url', { url, error })
     return Promise.reject({
       errorCode: CreateArticleSavingRequestErrorCode.BadData,
     })
diff --git a/packages/api/src/services/labels.ts b/packages/api/src/services/labels.ts
index 055c122ac..b29f9a775 100644
--- a/packages/api/src/services/labels.ts
+++ b/packages/api/src/services/labels.ts
@@ -6,7 +6,8 @@ import { Label } from '../entity/label'
 import { Link } from '../entity/link'
 import { User } from '../entity/user'
 import { CreateLabelInput } from '../generated/graphql'
-import { getRepository, labelRepository } from '../repository'
+import { entityManager, getRepository, setClaims } from '../repository'
+import { labelRepository } from '../repository/label'
 import { generateRandomColor } from '../utils/helpers'
 import { logger } from '../utils/logger'
 
@@ -120,35 +121,30 @@ export const createLabel = async (
   })
 }
 
-export const createLabels = async (
-  ctx: PageContext,
-  labels: CreateLabelInput[]
+export const getLabelsAndCreateIfNotExist = async (
+  labels: CreateLabelInput[],
+  userId: string
 ): Promise<Label[]> => {
-  const labelEntities = await labelRepository
-    .createQueryBuilder()
-    .where({
-      user: { id: ctx.uid },
-    })
-    .andWhere('LOWER(name) IN (:...names)', {
-      names: labels.map((l) => l.name.toLowerCase()),
-    })
-    .getMany()
+  return entityManager.transaction(async (tx) => {
+    await setClaims(tx, userId)
 
-  const existingLabelsInLowerCase = labelEntities.map((l) =>
-    l.name.toLowerCase()
-  )
-  const newLabels = labels.filter(
-    (l) => !existingLabelsInLowerCase.includes(l.name.toLowerCase())
-  )
-  // create new labels
-  const newLabelEntities = await labelRepository.save(
-    newLabels.map((l) => ({
-      name: l.name,
-      description: l.description,
-      color: l.color || generateRandomColor(),
-      internal: isLabelInternal(l.name),
-      user: { id: ctx.uid },
-    }))
-  )
-  return [...labelEntities, ...newLabelEntities]
+    const labelRepo = tx.withRepository(labelRepository)
+    // find existing labels
+    const labelEntities = await labelRepo.findByNames(labels.map((l) => l.name))
+
+    const existingLabelsInLowerCase = labelEntities.map((l) =>
+      l.name.toLowerCase()
+    )
+    const newLabels = labels.filter(
+      (l) => !existingLabelsInLowerCase.includes(l.name.toLowerCase())
+    )
+    if (newLabels.length === 0) {
+      return labelEntities
+    }
+
+    // create new labels
+    const newLabelEntities = await labelRepo.createLabels(newLabels, userId)
+
+    return [...labelEntities, ...newLabelEntities]
+  })
 }
diff --git a/packages/api/src/services/save_file.ts b/packages/api/src/services/save_file.ts
index fd1377982..8ebb9ce42 100644
--- a/packages/api/src/services/save_file.ts
+++ b/packages/api/src/services/save_file.ts
@@ -12,7 +12,7 @@ import { entityManager, getRepository } from '../repository'
 import { WithDataSourcesContext } from '../resolvers/types'
 import { logger } from '../utils/logger'
 import { getStorageFileDetails } from '../utils/uploads'
-import { createLabels } from './labels'
+import { getLabelsAndCreateIfNotExist } from './labels'
 
 export const setFileUploadComplete = async (
   id: string,
@@ -55,7 +55,7 @@ export const saveFile = async (
     input.state === ArticleSavingRequestStatus.Archived ? new Date() : null
   // add labels to page
   const labels = input.labels
-    ? await createLabels(ctx, input.labels)
+    ? await getLabelsAndCreateIfNotExist(ctx, input.labels)
     : undefined
   if (input.state || input.labels) {
     const updated = await updatePage(
diff --git a/packages/api/src/services/save_page.ts b/packages/api/src/services/save_page.ts
index a481ce742..2e9ca5fdb 100644
--- a/packages/api/src/services/save_page.ts
+++ b/packages/api/src/services/save_page.ts
@@ -30,7 +30,7 @@ import {
 import { logger } from '../utils/logger'
 import { parsePreparedContent } from '../utils/parser'
 import { createPageSaveRequest } from './create_page_save_request'
-import { createLabels } from './labels'
+import { getLabelsAndCreateIfNotExist } from './labels'
 import { createLibraryItem } from './library_item'
 
 // where we can use APIs to fetch their underlying content.
@@ -99,7 +99,7 @@ export const savePage = async (
     input.state === ArticleSavingRequestStatus.Archived ? new Date() : null
   // add labels to page
   const labels = input.labels
-    ? await createLabels(ctx, input.labels)
+    ? await getLabelsAndCreateIfNotExist(ctx, input.labels)
     : undefined
 
   const isImported = input.source === 'csv-importer'
diff --git a/packages/api/src/services/save_url.ts b/packages/api/src/services/save_url.ts
index 82ebf7736..0ef42d120 100644
--- a/packages/api/src/services/save_url.ts
+++ b/packages/api/src/services/save_url.ts
@@ -6,7 +6,7 @@ import { PubsubClient } from '../pubsub'
 import { getRepository } from '../repository'
 import { logger } from '../utils/logger'
 import { createPageSaveRequest } from './create_page_save_request'
-import { createLabels } from './labels'
+import { getLabelsAndCreateIfNotExist } from './labels'
 
 interface SaveContext {
   pubsub: PubsubClient
@@ -24,7 +24,7 @@ export const saveUrl = async (
       input.state === ArticleSavingRequestStatus.Archived ? new Date() : null
     // add labels to page
     const labels = input.labels
-      ? await createLabels(ctx, input.labels)
+      ? await getLabelsAndCreateIfNotExist(ctx, input.labels)
       : undefined
 
     const pageSaveRequest = await createPageSaveRequest({
diff --git a/packages/db/migrations/0118.do.library_item.sql b/packages/db/migrations/0118.do.library_item.sql
index f65d2112a..3a5f1e33e 100755
--- a/packages/db/migrations/0118.do.library_item.sql
+++ b/packages/db/migrations/0118.do.library_item.sql
@@ -55,9 +55,9 @@ CREATE TABLE omnivore.library_item (
     gcs_archive_id text,
     directionality directionality_type NOT NULL DEFAULT 'LTR',
     subscription_id uuid REFERENCES omnivore.subscriptions ON DELETE CASCADE,
-    label_names text[], -- array of label names of the item
-    highlight_labels text[], -- array of label names of the item's highlights
-    highlight_annotations text[], -- array of highlight annotations of the item
+    label_names text[] NOT NULL DEFAULT array[]::text[], -- array of label names of the item
+    highlight_labels text[] NOT NULL DEFAULT array[]::text[], -- array of label names of the item's highlights
+    highlight_annotations text[] NOT NULL DEFAULT array[]::text[], -- array of highlight annotations of the item
     note text,
     note_tsv tsvector,
     UNIQUE (user_id, original_url)
@@ -81,7 +81,7 @@ begin
     new.author_tsv := to_tsvector('pg_catalog.english', coalesce(new.author, ''));
     new.description_tsv := to_tsvector('pg_catalog.english', coalesce(new.description, ''));
     -- note_tsv is generated by both note and highlight_annotations
-    new.note_tsv := to_tsvector('pg_catalog.english', coalesce(new.note, '')) || to_tsvector('pg_catalog.english', string_agg(new.highlight_annotations, ' '));
+    new.note_tsv := to_tsvector('pg_catalog.english', coalesce(new.note, '') || ' ' || array_to_string(new.highlight_annotations, ' '));
     new.search_tsv := 
         setweight(new.title_tsv, 'A') || 
         setweight(new.author_tsv, 'A') || 
@@ -91,7 +91,7 @@ begin
         setweight(to_tsvector('pg_catalog.english', coalesce(regexp_replace(new.original_url, '^((http[s]?):\/)?\/?([^:\/\s]+)((\/\w+)*\/)([\w\-\.]+[^#?\s]+)(.*)?(#[\w\-]+)?$', '\3'), '')), 'A') || 
         -- secondary hostname (eg omnivore)
         setweight(to_tsvector('pg_catalog.english', coalesce(regexp_replace(new.original_url, '^((http[s]?):\/)?\/?(.*\.)?([^:\/\s]+)(\..*)((\/+)*\/)?([\w\-\.]+[^#?\s]+)(.*)?(#[\w\-]+)?$', '\4'), '')), 'A') ||
-        setweight(to_tsvector('pg_catalog.english', new.note_tsv), 'A') ||
+        setweight(new.note_tsv, 'A') ||
         setweight(new.content_tsv, 'B');
     return new;
 end
diff --git a/packages/db/migrations/0119.do.entity_labels.sql b/packages/db/migrations/0119.do.entity_labels.sql
index cae9aa63a..815e3bd5b 100755
--- a/packages/db/migrations/0119.do.entity_labels.sql
+++ b/packages/db/migrations/0119.do.entity_labels.sql
@@ -5,10 +5,62 @@
 BEGIN;
 
 CREATE TABLE omnivore.entity_labels (
+    id uuid PRIMARY KEY DEFAULT uuid_generate_v1mc(),
     library_item_id uuid REFERENCES omnivore.library_item(id) ON DELETE CASCADE,
     highlight_id uuid REFERENCES omnivore.highlight(id) ON DELETE CASCADE,
-    label_id uuid NOT NULL REFERENCES omnivore.labels(id) ON DELETE CASCADE,
-    PRIMARY KEY (library_item_id, highlight_id, label_id)
+    label_id uuid NOT NULL REFERENCES omnivore.labels(id) ON DELETE CASCADE
 );
 
+CREATE OR REPLACE FUNCTION update_library_item_labels()
+RETURNS trigger AS $$
+DECLARE
+    current_library_item_id uuid;
+    current_highlight_id uuid;
+BEGIN
+    IF TG_OP = 'DELETE' THEN
+        current_library_item_id = OLD.library_item_id;
+        current_highlight_id = OLD.highlight_id;
+    ELSE
+        current_library_item_id = NEW.library_item_id;
+        current_highlight_id = NEW.highlight_id;
+    END IF;
+
+    IF current_library_item_id IS NOT NULL THEN
+        -- for labels of the ABORTlibrary_item
+        WITH labels_agg AS (
+            SELECT array_agg(l.name) as names_agg
+            FROM omnivore.labels l
+            INNER JOIN omnivore.entity_labels el ON el.label_id = l.id AND el.library_item_id = current_library_item_id
+        )
+        -- Update label_names on library_item
+        UPDATE omnivore.library_item li
+        SET label_names = l.names_agg
+        FROM labels_agg l
+        WHERE li.id = current_library_item_id;
+    ELSIF current_highlight_id IS NOT NULL THEN
+        -- for labels of highlights of the library item
+        current_library_item_id = (SELECT library_item_id FROM omnivore.highlight WHERE id = current_highlight_id);
+
+        WITH labels_agg AS (
+            SELECT array_agg(l.name) as names_agg
+            FROM omnivore.labels l
+            INNER JOIN omnivore.entity_labels el ON el.label_id = l.id 
+            INNER JOIN omnivore.highlight h ON h.id = el.highlight_id AND h.library_item_id = current_library_item_id
+        )
+        -- Update highlight_labels on library_item
+        UPDATE omnivore.library_item li
+        SET highlight_labels = l.names_agg
+        FROM labels_agg l
+        WHERE li.id = current_library_item_id;
+    END IF;
+
+    return NEW;
+END;
+$$ LANGUAGE plpgsql;
+
+CREATE TRIGGER library_item_labels_update
+AFTER INSERT OR UPDATE OR DELETE ON omnivore.entity_labels
+FOR EACH ROW
+EXECUTE FUNCTION update_library_item_labels();
+
 COMMIT;
diff --git a/packages/db/migrations/0119.undo.entity_labels.sql b/packages/db/migrations/0119.undo.entity_labels.sql
index 35d1f1576..01877c022 100755
--- a/packages/db/migrations/0119.undo.entity_labels.sql
+++ b/packages/db/migrations/0119.undo.entity_labels.sql
@@ -4,6 +4,9 @@
 
 BEGIN;
 
+DROP TRIGGER library_item_labels_update ON omnivore.entity_labels;
+DROP FUNCTION update_library_item_labels();
+
 DROP TABLE omnivore.entity_labels;
 
 COMMIT;
diff --git a/packages/db/migrations/0121.do.update_highlight.sql b/packages/db/migrations/0121.do.update_highlight.sql
index aaad3f80a..65078428d 100755
--- a/packages/db/migrations/0121.do.update_highlight.sql
+++ b/packages/db/migrations/0121.do.update_highlight.sql
@@ -20,4 +20,34 @@ ALTER TABLE omnivore.highlight
     DROP COLUMN article_id,
     DROP COLUMN elastic_page_id;
 
+CREATE OR REPLACE FUNCTION update_library_item_highlight_annotations()
+RETURNS TRIGGER AS $$
+DECLARE
+    current_library_item_id uuid;
+BEGIN
+    IF TG_OP = 'INSERT' OR TG_OP = 'UPDATE' THEN
+        current_library_item_id = NEW.library_item_id;
+    ELSE
+        current_library_item_id = OLD.library_item_id;
+    END IF;
+
+    WITH highlight_agg AS (
+        SELECT array_agg(coalesce(annotation, '')) AS annotation_agg
+        FROM omnivore.highlight
+        WHERE library_item_id = current_library_item_id
+    )
+    UPDATE omnivore.library_item li
+    SET highlight_annotations = h.annotation_agg
+    FROM highlight_agg h
+    WHERE li.id = current_library_item_id;
+
+    RETURN NEW;
+END;
+$$ LANGUAGE plpgsql;
+
+CREATE TRIGGER library_item_highlight_annotations_update
+AFTER INSERT OR UPDATE OR DELETE ON omnivore.highlight
+FOR EACH ROW
+EXECUTE FUNCTION update_library_item_highlight_annotations();
+
 COMMIT;
diff --git a/packages/db/migrations/0121.undo.update_highlight.sql b/packages/db/migrations/0121.undo.update_highlight.sql
index 8f8d435d7..f7a989984 100755
--- a/packages/db/migrations/0121.undo.update_highlight.sql
+++ b/packages/db/migrations/0121.undo.update_highlight.sql
@@ -4,6 +4,9 @@
 
 BEGIN;
 
+DROP TRIGGER IF EXISTS library_item_highlight_annotations_update ON omnivore.highlight;
+DROP FUNCTION IF EXISTS update_library_item_highlight_annotations();
+
 ALTER TABLE omnivore.highlight 
     ADD COLUMN article_id uuid,
     ADD COLUMN elastic_page_id uuid,