diff --git a/ts/types/MessageAttachment.ts b/ts/types/MessageAttachment.ts
index a997f2425..32d069f5f 100644
--- a/ts/types/MessageAttachment.ts
+++ b/ts/types/MessageAttachment.ts
@@ -28,6 +28,17 @@ export const deleteExternalMessageFiles = async (message: {
 
   if (attachments && attachments.length) {
     await Promise.all(attachments.map(deleteData));
+    // testing that the files were successfully deleted
+    try {
+      await Promise.all(
+        attachments.map(async (attachment: { path: string; thumbnail: any; screenshot: any }) => {
+          await readAttachmentData(attachment.path);
+        })
+      );
+      window.log.info(`WIP: failed in deleting files`);
+    } catch (err) {
+      window.log.info(`WIP: succeeded in deleting files`, err);
+    }
   }
 
   if (quote && quote.attachments && quote.attachments.length) {
diff --git a/ts/types/attachments/migrations.ts b/ts/types/attachments/migrations.ts
index 5626803d6..cc7870833 100644
--- a/ts/types/attachments/migrations.ts
+++ b/ts/types/attachments/migrations.ts
@@ -145,26 +145,27 @@ export const loadData = async (attachment: any) => {
 //      deleteData :: (RelativePath -> IO Unit)
 //                    Attachment ->
 //                    IO Unit
-export const deleteData = () => {
-  return async (attachment: { path: string; thumbnail: any; screenshot: any }) => {
-    if (!isValid(attachment)) {
-      throw new TypeError('deleteData: attachment is not valid');
-    }
+// NOTE Flattening this function seemed to have worked
+export const deleteData = async (attachment: { path: string; thumbnail: any; screenshot: any }) => {
+  if (!isValid(attachment)) {
+    throw new TypeError('deleteData: attachment is not valid');
+  }
 
-    const { path, thumbnail, screenshot } = attachment;
-    if (isString(path)) {
-      await deleteOnDisk(path);
-    }
+  const { path, thumbnail, screenshot } = attachment;
 
-    if (thumbnail && isString(thumbnail.path)) {
-      await deleteOnDisk(thumbnail.path);
-    }
+  if (isString(path)) {
+    await deleteOnDisk(path);
+  }
 
-    if (screenshot && isString(screenshot.path)) {
-      await deleteOnDisk(screenshot.path);
-    }
-  };
+  if (thumbnail && isString(thumbnail.path)) {
+    await deleteOnDisk(thumbnail.path);
+  }
+
+  if (screenshot && isString(screenshot.path)) {
+    await deleteOnDisk(screenshot.path);
+  }
 };
+
 type CaptureDimensionType = { contentType: string; path: string };
 
 export const captureDimensionsAndScreenshot = async (
diff --git a/ts/util/expiringMessages.ts b/ts/util/expiringMessages.ts
index feee80527..9bfe2f5f3 100644
--- a/ts/util/expiringMessages.ts
+++ b/ts/util/expiringMessages.ts
@@ -49,8 +49,16 @@ export async function destroyMessagesAndUpdateRedux(
   const conversationWithChanges = uniq(messages.map(m => m.conversationKey));
 
   try {
+    const messageIds = messages.map(m => m.messageId);
+
+    // Delete any attachments
+    for (let i = 0; i < messageIds.length; i++) {
+      const message = await Data.getMessageById(messageIds[i]);
+      await message?.cleanup();
+    }
+
     // Delete all those messages in a single sql call
-    await Data.removeMessagesByIds(messages.map(m => m.messageId));
+    await Data.removeMessagesByIds(messageIds);
   } catch (e) {
     window.log.error('destroyMessages: removeMessagesByIds failed', e && e.message ? e.message : e);
   }