diff --git a/packages/api/src/services/integrations.ts b/packages/api/src/services/integrations.ts
index 01065f371..8cddb4398 100644
--- a/packages/api/src/services/integrations.ts
+++ b/packages/api/src/services/integrations.ts
@@ -1,6 +1,22 @@
 import { IntegrationType } from '../generated/graphql'
 import { env } from '../env'
 import axios from 'axios'
+import { wait } from '../utils/helpers'
+
+export interface ReadwiseHighlight {
+  text: string // The highlight text, (technically the only field required in a highlight object)
+  title?: string // The title of the page the highlight is on
+  author?: string // The author of the page the highlight is on
+  image_url?: string // The URL of the page image
+  source_url?: string // The URL of the page
+  source_type?: string // A meaningful unique identifier for your app
+  category?: string // One of: books, articles, tweets or podcasts
+  note?: string // Annotation note attached to the specific highlight
+  location?: number // Highlight's location in the source text. Used to order the highlights
+  location_type?: string // One of: page, order or time_offset
+  highlighted_at?: string // A datetime representing when the highlight was taken in the ISO 8601 format
+  highlight_url?: string // Unique url of the specific highlight
+}
 
 const READWISE_API_URL = 'https://readwise.io/api/v2'
 
@@ -18,10 +34,56 @@ export const validateToken = async (
 
 const validateReadwiseToken = async (token: string): Promise<boolean> => {
   const authUrl = `${env.readwise.apiUrl || READWISE_API_URL}/auth`
-  const response = await axios.get(authUrl, {
-    headers: {
-      Authorization: `Token ${token}`,
-    },
-  })
-  return response.status === 204
+  try {
+    const response = await axios.get(authUrl, {
+      headers: {
+        Authorization: `Token ${token}`,
+      },
+    })
+    return response.status === 204
+  } catch (error) {
+    console.log('error validating readwise token', error)
+    return false
+  }
+}
+
+export const createHighlightsInReadwise = async (
+  token: string,
+  highlights: ReadwiseHighlight[],
+  retryCount = 0
+): Promise<boolean> => {
+  const url = `${env.readwise.apiUrl || READWISE_API_URL}/highlights`
+  try {
+    const response = await axios.post(
+      url,
+      {
+        highlights: highlights.map((highlight) => ({
+          ...highlight,
+          source_type: 'omnivore',
+        })),
+      },
+      {
+        headers: {
+          Authorization: `Token ${token}`,
+          ContentType: 'application/json',
+        },
+      }
+    )
+    return response.status === 200
+  } catch (error) {
+    if (
+      axios.isAxiosError(error) &&
+      error.response?.status === 429 &&
+      retryCount < 3
+    ) {
+      console.log('Readwise API rate limit exceeded, retrying...')
+      // wait for Retry-After seconds in the header if rate limited
+      // max retry count is 3
+      const retryAfter = error.response?.headers['Retry-After'] || '10' // default to 10 seconds
+      await wait(parseInt(retryAfter, 10) * 1000)
+      return createHighlightsInReadwise(token, highlights, retryCount + 1)
+    }
+    console.log('Error creating highlights in Readwise', error)
+    return false
+  }
 }
diff --git a/packages/api/src/utils/helpers.ts b/packages/api/src/utils/helpers.ts
index 70cdb1154..98a9de742 100644
--- a/packages/api/src/utils/helpers.ts
+++ b/packages/api/src/utils/helpers.ts
@@ -254,3 +254,9 @@ export const validateUuid = (str: string): boolean => {
 export const isString = (check: any): check is string => {
   return typeof check === 'string' || check instanceof String
 }
+
+export const wait = (ms: number): Promise<void> => {
+  return new Promise((resolve) => {
+    setTimeout(resolve, ms)
+  })
+}