diff --git a/preload.js b/preload.js
index 994ddd509..fe079f40d 100644
--- a/preload.js
+++ b/preload.js
@@ -60,13 +60,18 @@ try {
   window.getAppInstance = () => config.appInstance;
   window.getVersion = () => config.version;
   window.getExpiration = () => {
+    const sixtyDays = 60 * 86400 * 1000;
     const remoteBuildExpiration = window.storage.get('remoteBuildExpiration');
+    const localBuildExpiration = window.Events.getAutoDownloadUpdate()
+      ? config.buildExpiration
+      : config.buildExpiration - sixtyDays;
+
     if (remoteBuildExpiration) {
       return remoteBuildExpiration < config.buildExpiration
         ? remoteBuildExpiration
-        : config.buildExpiration;
+        : localBuildExpiration;
     }
-    return config.buildExpiration;
+    return localBuildExpiration;
   };
   window.getNodeVersion = () => config.node_version;
   window.getHostName = () => config.hostname;
diff --git a/ts/updater/macos.ts b/ts/updater/macos.ts
index ea5d16c24..48a7409c2 100644
--- a/ts/updater/macos.ts
+++ b/ts/updater/macos.ts
@@ -20,7 +20,6 @@ import {
   getPrintableError,
   setUpdateListener,
   UpdaterInterface,
-  UpdateInformationType,
 } from './common';
 import { LoggerType } from '../types/Logging';
 import { hexToBinary, verifySignature } from './signature';
@@ -75,13 +74,23 @@ async function checkForUpdatesMaybeInstall(
 
   const { fileName: newFileName, version: newVersion } = result;
 
-  setUpdateListener(createUpdater(getMainWindow, result, logger));
-
   if (fileName !== newFileName || !version || gt(newVersion, version)) {
     const autoDownloadUpdates = await getAutoDownloadUpdateSetting(
       getMainWindow()
     );
     if (!autoDownloadUpdates) {
+      setUpdateListener(async () => {
+        logger.info(
+          'performUpdate: have not downloaded update, going to download'
+        );
+        await downloadAndInstall(
+          newFileName,
+          newVersion,
+          getMainWindow,
+          logger,
+          true
+        );
+      });
       getMainWindow().webContents.send(
         'show-update-dialog',
         DialogType.DownloadReady,
@@ -166,6 +175,11 @@ async function downloadAndInstall(
     //   because Squirrel has cached the update file and will do the right thing.
     logger.info('downloadAndInstall: showing update dialog...');
 
+    setUpdateListener(() => {
+      logger.info('performUpdate: calling quitAndInstall...');
+      markShouldQuit();
+      autoUpdater.quitAndInstall();
+    });
     getMainWindow().webContents.send('show-update-dialog', DialogType.Update, {
       version,
     });
@@ -380,28 +394,3 @@ function shutdown(
     );
   }
 }
-
-function createUpdater(
-  getMainWindow: () => BrowserWindow,
-  info: Pick<UpdateInformationType, 'fileName' | 'version'>,
-  logger: LoggerType
-) {
-  return async () => {
-    if (updateFilePath) {
-      logger.info('performUpdate: calling quitAndInstall...');
-      markShouldQuit();
-      autoUpdater.quitAndInstall();
-    } else {
-      logger.info(
-        'performUpdate: have not downloaded update, going to download'
-      );
-      await downloadAndInstall(
-        info.fileName,
-        info.version,
-        getMainWindow,
-        logger,
-        true
-      );
-    }
-  };
-}
diff --git a/ts/updater/windows.ts b/ts/updater/windows.ts
index 3d401e7e1..e81083da9 100644
--- a/ts/updater/windows.ts
+++ b/ts/updater/windows.ts
@@ -18,7 +18,6 @@ import {
   getPrintableError,
   setUpdateListener,
   UpdaterInterface,
-  UpdateInformationType,
 } from './common';
 import { LoggerType } from '../types/Logging';
 import { hexToBinary, verifySignature } from './signature';
@@ -78,13 +77,23 @@ async function checkForUpdatesMaybeInstall(
 
   const { fileName: newFileName, version: newVersion } = result;
 
-  setUpdateListener(createUpdater(getMainWindow, result, logger));
-
   if (fileName !== newFileName || !version || gt(newVersion, version)) {
     const autoDownloadUpdates = await getAutoDownloadUpdateSetting(
       getMainWindow()
     );
     if (!autoDownloadUpdates) {
+      setUpdateListener(async () => {
+        logger.info(
+          'performUpdate: have not downloaded update, going to download'
+        );
+        await downloadAndInstall(
+          newFileName,
+          newVersion,
+          getMainWindow,
+          logger,
+          true
+        );
+      });
       getMainWindow().webContents.send(
         'show-update-dialog',
         DialogType.DownloadReady,
@@ -138,6 +147,23 @@ async function downloadAndInstall(
     }
 
     logger.info('downloadAndInstall: showing dialog...');
+    setUpdateListener(async () => {
+      try {
+        await verifyAndInstall(updateFilePath, newVersion, logger);
+        installing = true;
+      } catch (error) {
+        logger.info('createUpdater: showing general update failure dialog...');
+        getMainWindow().webContents.send(
+          'show-update-dialog',
+          DialogType.Cannot_Update
+        );
+
+        throw error;
+      }
+
+      markShouldQuit();
+      app.quit();
+    });
     getMainWindow().webContents.send('show-update-dialog', DialogType.Update, {
       version,
     });
@@ -253,40 +279,3 @@ async function spawn(
     setTimeout(resolve, 200);
   });
 }
-
-function createUpdater(
-  getMainWindow: () => BrowserWindow,
-  info: Pick<UpdateInformationType, 'fileName' | 'version'>,
-  logger: LoggerType
-) {
-  return async () => {
-    if (updateFilePath) {
-      try {
-        await verifyAndInstall(updateFilePath, version, logger);
-        installing = true;
-      } catch (error) {
-        logger.info('createUpdater: showing general update failure dialog...');
-        getMainWindow().webContents.send(
-          'show-update-dialog',
-          DialogType.Cannot_Update
-        );
-
-        throw error;
-      }
-
-      markShouldQuit();
-      app.quit();
-    } else {
-      logger.info(
-        'performUpdate: have not downloaded update, going to download'
-      );
-      await downloadAndInstall(
-        info.fileName,
-        info.version,
-        getMainWindow,
-        logger,
-        true
-      );
-    }
-  };
-}
diff --git a/ts/util/hasExpired.ts b/ts/util/hasExpired.ts
index 750b9be92..744fa3dd9 100644
--- a/ts/util/hasExpired.ts
+++ b/ts/util/hasExpired.ts
@@ -1,9 +1,12 @@
 // Copyright 2020 Signal Messenger, LLC
 // SPDX-License-Identifier: AGPL-3.0-only
 
-const env = window.getEnvironment();
+import { Environment, getEnvironment } from '../environment';
+import { isInPast } from './timestamp';
 
-const NINETY_ONE_DAYS = 86400 * 91 * 1000;
+const ONE_DAY_MS = 86400 * 1000;
+const NINETY_ONE_DAYS = 91 * ONE_DAY_MS;
+const THIRTY_ONE_DAYS = 31 * ONE_DAY_MS;
 
 export function hasExpired(): boolean {
   const { getExpiration, log } = window;
@@ -21,18 +24,23 @@ export function hasExpired(): boolean {
     return true;
   }
 
-  const tooFarIntoFuture = Date.now() + NINETY_ONE_DAYS < buildExpiration;
+  if (getEnvironment() === Environment.Production) {
+    const safeExpirationMs = window.Events.getAutoDownloadUpdate()
+      ? NINETY_ONE_DAYS
+      : THIRTY_ONE_DAYS;
 
-  if (tooFarIntoFuture) {
-    log.error(
-      'Build expiration is set too far into the future',
-      buildExpiration
-    );
+    const buildExpirationDuration = buildExpiration - Date.now();
+    const tooFarIntoFuture = buildExpirationDuration > safeExpirationMs;
+
+    if (tooFarIntoFuture) {
+      log.error(
+        'Build expiration is set too far into the future',
+        buildExpiration
+      );
+    }
+
+    return tooFarIntoFuture || isInPast(buildExpiration);
   }
 
-  if (env === 'production') {
-    return Date.now() > buildExpiration && tooFarIntoFuture;
-  }
-
-  return buildExpiration !== 0 && Date.now() > buildExpiration;
+  return buildExpiration !== 0 && isInPast(buildExpiration);
 }
diff --git a/ts/util/timestamp.ts b/ts/util/timestamp.ts
index d2f924017..5fdf406ac 100644
--- a/ts/util/timestamp.ts
+++ b/ts/util/timestamp.ts
@@ -8,3 +8,11 @@ export function isMoreRecentThan(timestamp: number, delta: number): boolean {
 export function isOlderThan(timestamp: number, delta: number): boolean {
   return timestamp <= Date.now() - delta;
 }
+
+export function isInPast(timestamp: number): boolean {
+  return isOlderThan(timestamp, 0);
+}
+
+export function isInFuture(timestamp: number): boolean {
+  return isMoreRecentThan(timestamp, 0);
+}