diff --git a/app/attachment_channel.js b/app/attachment_channel.js
index 46a4b9ec88f..c5e22975150 100644
--- a/app/attachment_channel.js
+++ b/app/attachment_channel.js
@@ -11,8 +11,9 @@ module.exports = {
 let initialized = false;
 
 const ERASE_ATTACHMENTS_KEY = 'erase-attachments';
+const CLEANUP_ORPHANED_ATTACHMENTS_KEY = 'cleanup-orphaned-attachments';
 
-async function initialize({ configDir }) {
+async function initialize({ configDir, cleanupOrphanedAttachments }) {
   if (initialized) {
     throw new Error('initialze: Already initialized!');
   }
@@ -29,8 +30,19 @@ async function initialize({ configDir }) {
       event.sender.send(`${ERASE_ATTACHMENTS_KEY}-done`);
     } catch (error) {
       const errorForDisplay = error && error.stack ? error.stack : error;
-      console.log(`sql-erase error: ${errorForDisplay}`);
+      console.log(`erase attachments error: ${errorForDisplay}`);
       event.sender.send(`${ERASE_ATTACHMENTS_KEY}-done`, error);
     }
   });
+
+  ipcMain.on(CLEANUP_ORPHANED_ATTACHMENTS_KEY, async event => {
+    try {
+      await cleanupOrphanedAttachments();
+      event.sender.send(`${CLEANUP_ORPHANED_ATTACHMENTS_KEY}-done`);
+    } catch (error) {
+      const errorForDisplay = error && error.stack ? error.stack : error;
+      console.log(`cleanup orphaned attachments error: ${errorForDisplay}`);
+      event.sender.send(`${CLEANUP_ORPHANED_ATTACHMENTS_KEY}-done`, error);
+    }
+  });
 }
diff --git a/js/background.js b/js/background.js
index b9f6277d99c..d342e6f2a3b 100644
--- a/js/background.js
+++ b/js/background.js
@@ -408,6 +408,10 @@
     );
     window.log.info('Cleanup: complete');
 
+    if (newVersion) {
+      await window.Signal.Data.cleanupOrphanedAttachments();
+    }
+
     Views.Initialization.setMessage(window.i18n('loading'));
 
     // Note: We are not invoking the second set of IndexedDB migrations because it is
diff --git a/js/modules/data.js b/js/modules/data.js
index 0092cb99ef3..31b41b4add5 100644
--- a/js/modules/data.js
+++ b/js/modules/data.js
@@ -22,6 +22,7 @@ const DATABASE_UPDATE_TIMEOUT = 2 * 60 * 1000; // two minutes
 const SQL_CHANNEL_KEY = 'sql-channel';
 const ERASE_SQL_KEY = 'erase-sql-key';
 const ERASE_ATTACHMENTS_KEY = 'erase-attachments';
+const CLEANUP_ORPHANED_ATTACHMENTS_KEY = 'cleanup-orphaned-attachments';
 
 const _jobs = Object.create(null);
 const _DEBUG = false;
@@ -64,6 +65,7 @@ module.exports = {
 
   removeAll,
   removeOtherData,
+  cleanupOrphanedAttachments,
 
   // Returning plain JSON
   getMessagesNeedingUpgrade,
@@ -388,6 +390,10 @@ async function removeAll() {
   await channels.removeAll();
 }
 
+async function cleanupOrphanedAttachments() {
+  await callChannel(CLEANUP_ORPHANED_ATTACHMENTS_KEY);
+}
+
 // Note: will need to restart the app after calling this, to set up afresh
 async function removeOtherData() {
   await Promise.all([
diff --git a/main.js b/main.js
index 8bfda80183d..763798dbeb5 100644
--- a/main.js
+++ b/main.js
@@ -26,7 +26,7 @@ const packageJson = require('./package.json');
 
 const sql = require('./app/sql');
 const sqlChannels = require('./app/sql_channel');
-// const attachments = require('./app/attachments');
+const attachments = require('./app/attachments');
 const attachmentChannel = require('./app/attachment_channel');
 const autoUpdate = require('./app/auto_update');
 const createTrayIcon = require('./app/tray_icon');
@@ -618,8 +618,6 @@ app.on('ready', async () => {
     locale = loadLocale({ appLocale, logger });
   }
 
-  await attachmentChannel.initialize({ configDir: userDataPath });
-
   let key = userConfig.get('key');
   if (!key) {
     // https://www.zetetic.net/sqlcipher/sqlcipher-api/#key
@@ -630,12 +628,21 @@ app.on('ready', async () => {
   await sql.initialize({ configDir: userDataPath, key });
   await sqlChannels.initialize({ userConfig });
 
-  // const allAttachments = await attachments.getAllAttachments(userDataPath);
-  // const orphanedAttachments = await sql.removeKnownAttachments(allAttachments);
-  // await attachments.deleteAll({
-  //   userDataPath,
-  //   attachments: orphanedAttachments,
-  // });
+  async function cleanupOrphanedAttachments() {
+    const allAttachments = await attachments.getAllAttachments(userDataPath);
+    const orphanedAttachments = await sql.removeKnownAttachments(
+      allAttachments
+    );
+    await attachments.deleteAll({
+      userDataPath,
+      attachments: orphanedAttachments,
+    });
+  }
+
+  await attachmentChannel.initialize({
+    configDir: userDataPath,
+    cleanupOrphanedAttachments,
+  });
 
   ready = true;