diff --git a/packages/delivery-expo/delivery.js b/packages/delivery-expo/delivery.js
index 2b87879e..a888b88d 100644
--- a/packages/delivery-expo/delivery.js
+++ b/packages/delivery-expo/delivery.js
@@ -61,7 +61,14 @@ module.exports = (client, fetch = global.fetch) => {
         }
         client._logger.info(`Sending event ${event.events[0].errors[0].errorClass}: ${event.events[0].errors[0].errorMessage}`)
         send(url, opts, err => {
-          if (err) return onerror(err, { url, opts }, 'event', cb)
+          if (err) {
+            // do not retry oversized payloads regardless of status code
+            if (body.length > 10e5) {
+              client._logger.warn(`Discarding over-sized event (${body.length / 10e5} MB) after failed delivery`)
+              err.isRetryable = false
+            }
+            return onerror(err, { url, opts }, 'event', cb)
+          }
           cb(null)
         })
       } catch (e) {
diff --git a/packages/delivery-expo/test/delivery.test.js b/packages/delivery-expo/test/delivery.test.js
index a3c15e66..b13ec94f 100644
--- a/packages/delivery-expo/test/delivery.test.js
+++ b/packages/delivery-expo/test/delivery.test.js
@@ -202,6 +202,43 @@ describe('delivery: expo', () => {
     })
   })
 
+  it('does not attempt to re-send oversized payloads', done => {
+    // A 401 is considered retryable but this will be overridden by the payload size check
+    const { requests, server } = mockServer(401)
+    server.listen(err => {
+      expect(err).toBeUndefined()
+
+      const lotsOfEvents = []
+      while (JSON.stringify(lotsOfEvents).length < 10e5) {
+        lotsOfEvents.push({ errors: [{ errorClass: 'Error', errorMessage: 'long repetitive string'.repeat(1000) }] })
+      }
+      const payload = {
+        events: lotsOfEvents
+      }
+
+      const config = {
+        apiKey: 'aaaaaaaa',
+        endpoints: { notify: `http://0.0.0.0:${server.address().port}/notify/` },
+        redactedKeys: []
+      }
+
+      const logger = {
+        info: jest.fn(),
+        warn: jest.fn(),
+        error: jest.fn()
+      }
+
+      delivery({ _config: config, _logger: logger }, fetch).sendEvent(payload, (err) => {
+        expect(logger.warn).toHaveBeenCalledWith('Discarding over-sized event (1.014603 MB) after failed delivery')
+        expect(enqueueSpy).not.toHaveBeenCalled()
+        expect(err).toBeTruthy()
+        expect(requests.length).toBe(0)
+        server.close()
+        done()
+      })
+    })
+  })
+
   it('handles errors gracefully for sessions (ECONNREFUSED)', done => {
     const payload = {
       events: [{ errors: [{ errorClass: 'Error', errorMessage: 'foo is not a function' }] }]