diff --git a/src/main/index.js b/src/main/index.js
index eb5d53b6a..e880d562c 100644
--- a/src/main/index.js
+++ b/src/main/index.js
@@ -48,6 +48,20 @@ let daemonSubprocess;
 // if it dies when we didn't ask it to shut down, we want to alert the user.
 let daemonStopRequested = false;
 
+// This keeps track of whether a new file has been downloaded. We mostly
+// handle auto-update stuff in the render process, but need to know this
+// in order to display the extra confirmation dialog we show on close
+// on Windows.
+let updateDownloaded;
+if (process.platform === 'win32') {
+  updateDownloaded = false;
+}
+
+// This is used to keep track of whether we are showing he special dialog
+// that we show on Windows after you decline an upgrade and close the app later.
+let showingUpdateCloseAlert = false;
+
+
 // When a quit is attempted, we cancel the quit, do some preparations, then
 // this is set to true and app.quit() is called again to quit for real.
 let readyToQuit = false;
@@ -406,6 +420,10 @@ if (isDevelopment) {
     });
 }
 
+autoUpdater.on('update-downloaded', () => {
+  updateDownloaded = true;
+});
+
 app.setAsDefaultProtocolClient('lbry');
 
 app.on('ready', () => {
@@ -431,7 +449,12 @@ app.on('window-all-closed', () => {
 });
 
 app.on('before-quit', event => {
-  if (!readyToQuit) {
+  if (process.platform === 'darwin' && updateDownloaded && !showingUpdateCloseAlert) {
+    // We haven't shown the special dialog that we show on Windows
+    // if the user declines an update and then quits later
+    rendererWindow.webContents.send('quitRequested');
+    showingUpdateCloseAlert = true;
+  } else if (!readyToQuit) {
     // We need to shutdown the daemon before we're ready to actually quit. This
     // event will be triggered re-entrantly once preparation is done.
     event.preventDefault();
diff --git a/src/renderer/constants/modal_types.js b/src/renderer/constants/modal_types.js
index 8e56e8237..aba7e21aa 100644
--- a/src/renderer/constants/modal_types.js
+++ b/src/renderer/constants/modal_types.js
@@ -3,6 +3,7 @@ export const INCOMPATIBLE_DAEMON = 'incompatibleDaemon';
 export const FILE_TIMEOUT = 'file_timeout';
 export const DOWNLOADING = 'downloading';
 export const AUTO_UPDATE_DOWNLOADED = "auto_update_downloaded";
+export const UPDATE_CLOSE_ALERT = "updateCloseAlert";
 export const ERROR = 'error';
 export const INSUFFICIENT_CREDITS = 'insufficient_credits';
 export const UPGRADE = 'upgrade';
diff --git a/src/renderer/index.js b/src/renderer/index.js
index cafd41c35..cd9ab98ff 100644
--- a/src/renderer/index.js
+++ b/src/renderer/index.js
@@ -9,7 +9,7 @@ import lbry from 'lbry';
 import React from 'react';
 import ReactDOM from 'react-dom';
 import { Provider } from 'react-redux';
-import { doConditionalAuthNavigate, doDaemonReady, doShowSnackBar, doAutoUpdate } from 'redux/actions/app';
+import { doConditionalAuthNavigate, doOpenModal, doDaemonReady, doShowSnackBar, doAutoUpdate } from 'redux/actions/app';
 import { doNavigate } from 'redux/actions/navigation';
 import { doDownloadLanguages } from 'redux/actions/settings';
 import { doUserEmailVerify } from 'redux/actions/user';
@@ -62,7 +62,7 @@ ipcRenderer.on('window-is-focused', () => {
   dock.setBadge('');
 });
 
-((history, ...args) => {
+(function(history, ...args) {
   const { replaceState } = history;
   const newHistory = history;
   newHistory.replaceState = (_, __, path) => {
diff --git a/src/renderer/modal/modalAutoUpdateDownloaded/index.js b/src/renderer/modal/modalAutoUpdateDownloaded/index.js
index 740a2dca2..0ce6cdcbe 100644
--- a/src/renderer/modal/modalAutoUpdateDownloaded/index.js
+++ b/src/renderer/modal/modalAutoUpdateDownloaded/index.js
@@ -2,6 +2,7 @@ import React from "react";
 import { connect } from "react-redux";
 import { doCloseModal } from "redux/actions/app";
 import ModalAutoUpdateDownloaded from "./view";
+import { doCloseModal } from "redux/actions/app";
 
 const perform = dispatch => ({
   closeModal: () => dispatch(doCloseModal()),
diff --git a/src/renderer/modal/modalRouter/view.jsx b/src/renderer/modal/modalRouter/view.jsx
index 81925c966..a8fa1dfbf 100644
--- a/src/renderer/modal/modalRouter/view.jsx
+++ b/src/renderer/modal/modalRouter/view.jsx
@@ -3,6 +3,7 @@ import ModalError from 'modal/modalError';
 import ModalAuthFailure from 'modal/modalAuthFailure';
 import ModalDownloading from 'modal/modalDownloading';
 import ModalAutoUpdateDownloaded from "modal/modalAutoUpdateDownloaded";
+import ModalUpdateCloseAlert from "modal/modalUpdateCloseAlert";
 import ModalUpgrade from 'modal/modalUpgrade';
 import ModalWelcome from 'modal/modalWelcome';
 import ModalFirstReward from 'modal/modalFirstReward';
@@ -105,6 +106,8 @@ class ModalRouter extends React.PureComponent {
         return <ModalDownloading {...modalProps} />;
       case modals.AUTO_UPDATE_DOWNLOADED:
         return <ModalAutoUpdateDownloaded {...modalProps} />;
+      case modals.UPDATE_CLOSE_ALERT:
+        return <ModalUpdateCloseAlert {...modalProps} />;
       case modals.ERROR:
         return <ModalError {...modalProps} />;
       case modals.FILE_TIMEOUT:
diff --git a/src/renderer/modal/modalUpdateCloseAlert/index.js b/src/renderer/modal/modalUpdateCloseAlert/index.js
new file mode 100644
index 000000000..caff049a6
--- /dev/null
+++ b/src/renderer/modal/modalUpdateCloseAlert/index.js
@@ -0,0 +1,12 @@
+import React from 'react';
+import { connect } from 'react-redux';
+import { doQuit } from 'redux/actions/app';
+import ModalUpdateCloseAlert from './view';
+
+const select = state => ({});
+
+const perform = dispatch => ({
+  quit: () => dispatch(doSkipUpgrade()),
+});
+
+export default connect(select, perform)(ModalUpdateCloseAlert);
diff --git a/src/renderer/modal/modalUpdateCloseAlert/view.jsx b/src/renderer/modal/modalUpdateCloseAlert/view.jsx
new file mode 100644
index 000000000..9f0b28c3a
--- /dev/null
+++ b/src/renderer/modal/modalUpdateCloseAlert/view.jsx
@@ -0,0 +1,23 @@
+import React from 'react';
+import { Modal } from 'modal/modal';
+import Link from 'component/link';
+
+class ModalUpdateCloseAlert extends React.PureComponent {
+  render() {
+    const { quit } = this.props;
+
+    return (
+      <Modal
+        isOpen
+        type="alert"
+        confirmButtonLabel={__('Close Now')}
+        onConfirmed={quit}
+      >
+        <h3 className="text-center">{__('LBRY Will Upgrade')}</h3>
+        <p>{__('Please select yes to the upgrade prompt shown after the app closes.')}</p>
+      </Modal>
+    );
+  }
+}
+
+export default ModalUpdateCloseAlert;
diff --git a/src/renderer/redux/actions/app.js b/src/renderer/redux/actions/app.js
index e2b36470b..8ae003bf7 100644
--- a/src/renderer/redux/actions/app.js
+++ b/src/renderer/redux/actions/app.js
@@ -110,8 +110,8 @@ export function doAutoUpdate() {
   return function(dispatch, getState) {
     const state = getState();
     dispatch({
-      type: types.OPEN_MODAL,
-      data: { modal: modals.AUTO_UPDATE_DOWNLOADED },
+      type: ACTIONS.OPEN_MODAL,
+      data: { modal: MODALS.AUTO_UPDATE_DOWNLOADED },
     });
   };
 }