diff --git a/electron/index.js b/electron/index.js
index 9671a6eb2..fda80eac3 100644
--- a/electron/index.js
+++ b/electron/index.js
@@ -36,26 +36,21 @@ try {
 autoUpdater.autoDownload = !upgradeDisabled;
 autoUpdater.allowPrerelease = false;
 
-// This is set to true if an auto update has been downloaded through the Electron
-// auto-update system and is ready to install. If the user declined an update earlier,
-// it will still install on shutdown.
-let autoUpdateDownloaded = false;
+const UPDATE_STATE_INIT = 0;
+const UPDATE_STATE_CHECKING = 1;
+const UPDATE_STATE_UPDATES_FOUND = 2;
+const UPDATE_STATE_NO_UPDATES_FOUND = 3;
+const UPDATE_STATE_DOWNLOADING = 4;
+const UPDATE_STATE_DOWNLOADED = 5;
+let updateState = UPDATE_STATE_INIT;
+let updateDownloadItem;
+
+const isAutoUpdateSupported = ['win32', 'darwin'].includes(process.platform) || !!process.env.APPIMAGE;
 
 // This is used to keep track of whether we are showing the special dialog
 // that we show on Windows after you decline an upgrade and close the app later.
 let showingAutoUpdateCloseAlert = false;
 
-// This is used to prevent downloading updates multiple times when
-// using the auto updater API.
-// As read in the documentation:
-// "Calling autoUpdater.checkForUpdates() twice will download the update two times."
-// https://www.electronjs.org/docs/latest/api/auto-updater#autoupdatercheckforupdates
-let keepCheckingForUpdates = true;
-
-let downloadUpgradeInitiated = false;
-
-let downloadUpgradeItem;
-
 // Keep a global reference, if you don't, they will be closed automatically when the JavaScript
 // object is garbage collected.
 let rendererWindow;
@@ -243,7 +238,8 @@ app.on('activate', () => {
 app.on('will-quit', event => {
   if (
     process.platform === 'win32' &&
-    autoUpdateDownloaded &&
+    updateState === UPDATE_STATE_DOWNLOADED &&
+    isAutoUpdateSupported &&
     !appState.autoUpdateAccepted &&
     !showingAutoUpdateCloseAlert
   ) {
@@ -327,124 +323,6 @@ ipcMain.on('get-disk-space', async (event) => {
   }
 });
 
-ipcMain.on('cancel-download-upgrade', () => {
-  if (downloadUpgradeItem) {
-    // Cancel the download and execute the onCancel
-    // callback set in the options.
-    downloadUpgradeItem.cancel();
-  }
-});
-
-ipcMain.on('download-upgrade', async (event, params) => {
-  // Prevent downloading multiple times.
-  if (downloadUpgradeInitiated || downloadUpgradeItem) {
-    return;
-  }
-  const { url, options } = params;
-  const dir = fs.mkdtempSync(app.getPath('temp') + path.sep);
-
-  downloadUpgradeInitiated = true;
-
-  // Grab the download item's handler to allow
-  // cancelling the operation if required.
-  options.onStarted = function(downloadItem) {
-    downloadUpgradeItem = downloadItem;
-  };
-  options.onCancel = function() {
-    downloadUpgradeItem = undefined;
-    downloadUpgradeInitiated = false;
-  };
-  options.onProgress = function(p) {
-    rendererWindow.webContents.send('download-progress-update', p);
-  };
-  options.directory = dir;
-  options.onCompleted = function(c) {
-    downloadUpgradeInitiated = false;
-    downloadUpgradeItem = undefined;
-    rendererWindow.webContents.send('download-update-complete', c);
-  };
-  const win = BrowserWindow.getFocusedWindow();
-  await download(win, url, options).catch(e => console.log('e', e));
-});
-
-ipcMain.on('upgrade', (event, installerPath) => {
-  // what to do if no shutdown in a long time?
-  console.log('Update downloaded to', installerPath);
-  console.log('The app will close and you will be prompted to install the latest version of LBRY.');
-  console.log('After the install is complete, please reopen the app.');
-
-  // Prevent .deb package from opening with archive manager (Ubuntu >= 20)
-  if (process.platform === 'linux' && !process.env.APPIMAGE) {
-    sudo.exec(`dpkg -i ${installerPath}`, { name: app.name }, (err, stdout, stderr) => {
-      if (err || stderr) {
-        rendererWindow.webContents.send('upgrade-installing-error');
-        return;
-      }
-
-      // Re-launch the application when the installation finishes.
-      app.relaunch();
-      app.quit();
-    });
-
-    return;
-  }
-
-  app.on('quit', () => {
-    console.log('Launching upgrade installer at', installerPath);
-    // This gets triggered called after *all* other quit-related events, so
-    // we'll only get here if we're fully prepared and quitting for real.
-    shell.openPath(installerPath);
-  });
-  app.quit();
-});
-
-ipcMain.on('check-for-updates', (event, autoDownload) => {
-  // Prevent downloading the same update multiple times.
-  if (!keepCheckingForUpdates) {
-    return;
-  }
-
-  keepCheckingForUpdates = false;
-  autoUpdater.autoDownload = autoDownload;
-  autoUpdater.checkForUpdates();
-});
-
-autoUpdater.on('update-downloaded', () => {
-  autoUpdateDownloaded = true;
-
-  // If this download was trigger by
-  // autoUpdateAccepted it means, the user
-  // wants to install the new update but
-  // needed to downloaded the files first.
-  if (appState.autoUpdateAccepted) {
-    autoUpdater.quitAndInstall();
-  }
-});
-
-autoUpdater.on('update-not-available', () => {
-  keepCheckingForUpdates = true;
-});
-
-ipcMain.on('autoUpdateAccepted', () => {
-  appState.autoUpdateAccepted = true;
-
-  // quitAndInstall can only be called if the
-  // update has been downloaded. Since the user
-  // can disable auto updates, we have to make
-  // sure it has been downloaded first.
-  if (autoUpdateDownloaded) {
-    autoUpdater.quitAndInstall();
-    return;
-  }
-
-  // If the update hasn't been downloaded,
-  // start downloading it. After it's done, the
-  // event 'update-downloaded' will be triggered,
-  // where we will be able to resume the
-  // update installation.
-  autoUpdater.downloadUpdate();
-});
-
 ipcMain.on('version-info-requested', () => {
   function formatRc(ver) {
     // Adds dash if needed to make RC suffix SemVer friendly
@@ -537,3 +415,147 @@ process.on('uncaughtException', error => {
   if (daemon) daemon.quit();
   app.exit(1);
 });
+
+// Auto updater
+// autoUpdater.on('download-progress', (p) => {
+//   rendererWindow.webContents.send('download-progress-update', p);
+// });
+
+autoUpdater.on('update-downloaded', () => {
+  updateState = UPDATE_STATE_DOWNLOADED;
+
+  // If this download was trigger by
+  // autoUpdateAccepted it means, the user
+  // wants to install the new update but
+  // needed to downloaded the files first.
+  if (appState.autoUpdateAccepted) {
+    autoUpdater.quitAndInstall();
+  }
+});
+
+autoUpdater.on('update-not-available', () => {
+  updateState = UPDATE_STATE_NO_UPDATES_FOUND;
+});
+
+autoUpdater.on('error', () => {
+  updateState = UPDATE_STATE_INIT;
+});
+
+// Manual (.deb) update
+ipcMain.on('cancel-download-upgrade', () => {
+  if (updateDownloadItem) {
+    // Cancel the download and execute the onCancel
+    // callback set in the options.
+    updateDownloadItem.cancel();
+  }
+});
+
+ipcMain.on('download-upgrade', (event, params) => {
+  if (updateState !== UPDATE_STATE_UPDATES_FOUND) {
+    return;
+  }
+  if (isAutoUpdateSupported) {
+    updateState = UPDATE_STATE_DOWNLOADING;
+    autoUpdater.downloadUpdate();
+    return;
+  }
+  
+  const { url, options } = params;
+  const dir = fs.mkdtempSync(app.getPath('temp') + path.sep);
+
+  updateState = UPDATE_STATE_DOWNLOADING;
+
+  // Grab the download item's handler to allow
+  // cancelling the operation if required.
+  options.onStarted = function(downloadItem) {
+    updateDownloadItem = downloadItem;
+  };
+  options.onCancel = function() {
+    updateState = UPDATE_STATE_UPDATES_FOUND;
+    updateDownloadItem = undefined;
+  };
+  options.onProgress = function(p) {
+    rendererWindow.webContents.send('download-progress-update', p);
+  };
+  options.onCompleted = function(c) {
+    updateState = UPDATE_STATE_DOWNLOADED;
+    updateDownloadItem = undefined;
+    rendererWindow.webContents.send('download-update-complete', c);
+  };
+  options.directory = dir;
+  const win = BrowserWindow.getFocusedWindow();
+  download(win, url, options).catch(e => {
+    updateState = UPDATE_STATE_UPDATES_FOUND;
+    console.log('e', e);
+  });
+});
+
+// Update behavior
+ipcMain.on('autoUpdateAccepted', () => {
+  appState.autoUpdateAccepted = true;
+
+  // quitAndInstall can only be called if the
+  // update has been downloaded. Since the user
+  // can disable auto updates, we have to make
+  // sure it has been downloaded first.
+  if (updateState === UPDATE_STATE_DOWNLOADED) {
+    autoUpdater.quitAndInstall();
+    return;
+  }
+
+  // If the update hasn't been downloaded,
+  // start downloading it. After it's done, the
+  // event 'update-downloaded' will be triggered,
+  // where we will be able to resume the
+  // update installation.
+  updateState = UPDATE_STATE_DOWNLOADING;
+  autoUpdater.downloadUpdate();
+});
+
+ipcMain.on('check-for-updates', (event, autoDownload) => {
+  if (![UPDATE_STATE_INIT, UPDATE_STATE_NO_UPDATES_FOUND].includes(updateState)) {
+    return;
+  }
+
+  updateState = UPDATE_STATE_CHECKING;
+
+  // If autoDownload is true, checkForUpdates will begin the
+  // download automatically.
+  if (autoDownload) {
+    updateState = UPDATE_STATE_DOWNLOADING;
+  }
+
+  autoUpdater.autoDownload = autoDownload;
+  autoUpdater.checkForUpdates();
+});
+
+ipcMain.on('upgrade', (event, installerPath) => {
+  // what to do if no shutdown in a long time?
+  console.log('Update downloaded to', installerPath);
+  console.log('The app will close and you will be prompted to install the latest version of LBRY.');
+  console.log('After the install is complete, please reopen the app.');
+
+  // Prevent .deb package from opening with archive manager (Ubuntu >= 20)
+  if (process.platform === 'linux' && !process.env.APPIMAGE) {
+    sudo.exec(`dpkg -i ${installerPath}`, { name: app.name }, (err, stdout, stderr) => {
+      if (err || stderr) {
+        rendererWindow.webContents.send('upgrade-installing-error');
+        return;
+      }
+
+      // Re-launch the application when the installation finishes.
+      app.relaunch();
+      app.quit();
+    });
+
+    return;
+  }
+
+  app.on('quit', () => {
+    console.log('Launching upgrade installer at', installerPath);
+    // This gets triggered called after *all* other quit-related events, so
+    // we'll only get here if we're fully prepared and quitting for real.
+    shell.openPath(installerPath);
+  });
+  app.quit();
+});
\ No newline at end of file
diff --git a/ui/constants/action_types.js b/ui/constants/action_types.js
index 37954c7e2..470f44c7f 100644
--- a/ui/constants/action_types.js
+++ b/ui/constants/action_types.js
@@ -57,6 +57,8 @@ export const UPDATE_REMOTE_VERSION = 'UPDATE_REMOTE_VERSION';
 export const SKIP_UPGRADE = 'SKIP_UPGRADE';
 export const START_UPGRADE = 'START_UPGRADE';
 export const AUTO_UPDATE_DECLINED = 'AUTO_UPDATE_DECLINED';
+export const AUTO_UPDATE_RESET = 'AUTO_UPDATE_RESET';
+export const AUTO_UPDATE_FAILED = 'AUTO_UPDATE_FAILED';
 export const AUTO_UPDATE_DOWNLOADED = 'AUTO_UPDATE_DOWNLOADED';
 export const CLEAR_UPGRADE_TIMER = 'CLEAR_UPGRADE_TIMER';
 
diff --git a/ui/index.jsx b/ui/index.jsx
index b31b4e418..00b72e6df 100644
--- a/ui/index.jsx
+++ b/ui/index.jsx
@@ -22,6 +22,8 @@ import {
   doUpdateDownloadProgress,
   doNotifyUpdateAvailable,
   doShowUpgradeInstallationError,
+  doAutoUpdateReset,
+  doAutoUpdateFail,
 } from 'redux/actions/app';
 import { isURIValid } from 'util/lbryURI';
 import { setSearchApi } from 'redux/actions/search';
@@ -129,10 +131,23 @@ ipcRenderer.on('open-uri-requested', (event, url, newSession) => {
   handleError();
 });
 
+autoUpdater.on('checking-for-update', () => {
+  app.store.dispatch(doAutoUpdateReset());
+});
+
 autoUpdater.on('update-available', (e) => {
+  app.store.dispatch(doAutoUpdateReset());
   app.store.dispatch(doNotifyUpdateAvailable(e));
 });
 
+autoUpdater.on('update-downloaded', () => {
+  app.store.dispatch(doAutoUpdateReset());
+});
+
+autoUpdater.on('error', () => {
+  app.store.dispatch(doAutoUpdateFail());
+});
+
 ipcRenderer.on('upgrade-installing-error', () => {
   app.store.dispatch(doShowUpgradeInstallationError());
 });
diff --git a/ui/modal/modalAutoUpdateDownloaded/index.js b/ui/modal/modalAutoUpdateDownloaded/index.js
index afe8e8fa4..2b98538dd 100644
--- a/ui/modal/modalAutoUpdateDownloaded/index.js
+++ b/ui/modal/modalAutoUpdateDownloaded/index.js
@@ -1,13 +1,15 @@
 import { connect } from 'react-redux';
 import { doAutoUpdateDeclined, doHideModal } from 'redux/actions/app';
+import { selectAutoUpdateFailed } from 'redux/selectors/app';
 import ModalAutoUpdateDownloaded from './view';
 
-const perform = dispatch => ({
+const select = (state, props) => ({
+  errorWhileUpdating: selectAutoUpdateFailed(state),
+});
+
+const perform = (dispatch) => ({
   closeModal: () => dispatch(doHideModal()),
   declineAutoUpdate: () => dispatch(doAutoUpdateDeclined()),
 });
 
-export default connect(
-  null,
-  perform
-)(ModalAutoUpdateDownloaded);
+export default connect(select, perform)(ModalAutoUpdateDownloaded);
diff --git a/ui/modal/modalAutoUpdateDownloaded/view.jsx b/ui/modal/modalAutoUpdateDownloaded/view.jsx
index aecb049b4..7110cfb94 100644
--- a/ui/modal/modalAutoUpdateDownloaded/view.jsx
+++ b/ui/modal/modalAutoUpdateDownloaded/view.jsx
@@ -7,13 +7,15 @@ import { Modal } from 'modal/modal';
 import LastReleaseChanges from 'component/lastReleaseChanges';
 
 type Props = {
-  closeModal: any => any,
+  closeModal: (any) => any,
   declineAutoUpdate: () => any,
+  errorWhileUpdating: boolean,
 };
 
 const ModalAutoUpdateDownloaded = (props: Props) => {
-  const { closeModal, declineAutoUpdate } = props;
+  const { closeModal, declineAutoUpdate, errorWhileUpdating } = props;
   const [disabled, setDisabled] = useState(false);
+  const isDownloading = disabled && !errorWhileUpdating;
 
   const handleConfirm = () => {
     setDisabled(true);
@@ -31,13 +33,14 @@ const ModalAutoUpdateDownloaded = (props: Props) => {
       type="confirm"
       contentLabel={__('Upgrade Downloaded')}
       title={__('LBRY leveled up')}
-      confirmButtonLabel={__('Upgrade Now')}
+      confirmButtonLabel={isDownloading ? __('Downloading...') : __('Upgrade Now')}
       abortButtonLabel={__('Not Now')}
-      confirmButtonDisabled={disabled}
+      confirmButtonDisabled={isDownloading}
       onConfirmed={handleConfirm}
       onAborted={handleAbort}
     >
       <LastReleaseChanges />
+      {errorWhileUpdating && <p>__('There was an error while updating. Please try again.')</p>}
     </Modal>
   );
 };
diff --git a/ui/redux/actions/app.js b/ui/redux/actions/app.js
index f8916d36e..f4aaa2c46 100644
--- a/ui/redux/actions/app.js
+++ b/ui/redux/actions/app.js
@@ -220,6 +220,18 @@ export function doNotifyUpdateAvailable(e) {
   };
 }
 
+export function doAutoUpdateReset() {
+  return {
+    type: ACTIONS.AUTO_UPDATE_RESET,
+  };
+}
+
+export function doAutoUpdateFail() {
+  return {
+    type: ACTIONS.AUTO_UPDATE_FAILED,
+  };
+}
+
 /*
   Initiate a timer that will check for an app upgrade every 10 minutes.
  */
diff --git a/ui/redux/reducers/app.js b/ui/redux/reducers/app.js
index 5426e56b8..41ec971b5 100644
--- a/ui/redux/reducers/app.js
+++ b/ui/redux/reducers/app.js
@@ -27,6 +27,7 @@ export type AppState = {
   badgeNumber: number,
   volume: number,
   autoUpdateDeclined: boolean,
+  autoUpdateFailed: boolean,
   modalsAllowed: boolean,
   downloadProgress: ?number,
   upgradeDownloading: ?boolean,
@@ -64,6 +65,7 @@ const defaultState: AppState = {
   muted: false,
   autoUpdateDownloaded: false,
   autoUpdateDeclined: false,
+  autoUpdateFailed: false,
   modalsAllowed: true,
   hasClickedComment: false,
   downloadProgress: undefined,
@@ -152,6 +154,16 @@ reducers[ACTIONS.AUTO_UPDATE_DECLINED] = (state) =>
     autoUpdateDeclined: true,
   });
 
+reducers[ACTIONS.AUTO_UPDATE_RESET] = (state) =>
+  Object.assign({}, state, {
+    autoUpdateFailed: false,
+  });
+
+reducers[ACTIONS.AUTO_UPDATE_FAILED] = (state) =>
+  Object.assign({}, state, {
+    autoUpdateFailed: true,
+  });
+
 reducers[ACTIONS.UPGRADE_DOWNLOAD_COMPLETED] = (state, action) =>
   Object.assign({}, state, {
     downloadPath: action.data.path,
diff --git a/ui/redux/selectors/app.js b/ui/redux/selectors/app.js
index 920267b62..8e1cefeb9 100644
--- a/ui/redux/selectors/app.js
+++ b/ui/redux/selectors/app.js
@@ -54,6 +54,8 @@ export const selectAutoUpdateDownloaded = createSelector(selectState, (state) =>
 
 export const selectAutoUpdateDeclined = createSelector(selectState, (state) => state.autoUpdateDeclined);
 
+export const selectAutoUpdateFailed = createSelector(selectState, (state) => state.autoUpdateFailed);
+
 export const selectIsUpdateModalDisplayed = createSelector(selectState, (state) => {
   return [MODALS.AUTO_UPDATE_DOWNLOADED, MODALS.UPGRADE, MODALS.DOWNLOADING].includes(state.modal);
 });