diff --git a/ts/types/MessageAttachment.ts b/ts/types/MessageAttachment.ts
index 199d33908..683efd24f 100644
--- a/ts/types/MessageAttachment.ts
+++ b/ts/types/MessageAttachment.ts
@@ -10,6 +10,7 @@ import {
   autoOrientJPEGAttachment,
   captureDimensionsAndScreenshot,
   deleteData,
+  deleteDataSuccessful,
   loadData,
   replaceUnicodeV2,
 } from './attachments/migrations';
@@ -30,14 +31,14 @@ export const deleteExternalMessageFiles = async (message: {
     await Promise.all(attachments.map(deleteData));
     // test that the files were deleted successfully
     try {
-      await Promise.all(
-        attachments.map(async (attachment: { path: string; thumbnail: any; screenshot: any }) => {
-          await readAttachmentData(attachment.path);
-        })
-      );
-      window.log.info('[deleteExternalMessageFiles]: Failed to delete attachments for', message);
+      let results = await Promise.allSettled(attachments.map(deleteDataSuccessful));
+      results = results.filter(result => result.status === 'rejected');
+
+      if (results.length) {
+        throw Error;
+      }
     } catch (err) {
-      // If we fail to read the path then we know we deleted successfully
+      window.log.warn('[deleteExternalMessageFiles]: Failed to delete attachments for', message);
     }
   }
 
diff --git a/ts/types/attachments/migrations.ts b/ts/types/attachments/migrations.ts
index 44221d420..0624b10e9 100644
--- a/ts/types/attachments/migrations.ts
+++ b/ts/types/attachments/migrations.ts
@@ -2,6 +2,7 @@ import * as GoogleChrome from '../../../ts/util/GoogleChrome';
 import * as MIME from '../../../ts/types/MIME';
 import { toLogFormat } from './Errors';
 import { arrayBufferToBlob, blobToArrayBuffer } from 'blob-util';
+import fse from 'fs-extra';
 
 import { isString } from 'lodash';
 import {
@@ -170,6 +171,27 @@ export const deleteData = async (attachment: { path: string; thumbnail: any; scr
   return attachment;
 };
 
+export const deleteDataSuccessful = async (attachment: {
+  path: string;
+  thumbnail: any;
+  screenshot: any;
+}) => {
+  const errorMessage = `deleteDataSuccessful: Deletion failed for attachment ${attachment.path}`;
+  return fse.pathExists(attachment.path, (err, exists) => {
+    if (err) {
+      return Promise.reject(`${errorMessage} ${err}`);
+    }
+
+    // Note we want to confirm the path no longer exists
+    if (exists) {
+      return Promise.reject(errorMessage);
+    }
+
+    window.log.debug(`deleteDataSuccessful: Deletion succeeded for attachment ${attachment.path}`);
+    return true;
+  });
+};
+
 type CaptureDimensionType = { contentType: string; path: string };
 
 export const captureDimensionsAndScreenshot = async (