diff --git a/ts/updater/common.ts b/ts/updater/common.ts
index 2f877499c..7a03dc80f 100644
--- a/ts/updater/common.ts
+++ b/ts/updater/common.ts
@@ -4,7 +4,7 @@
 /* eslint-disable no-console */
 import { createWriteStream } from 'fs';
 import { pathExists } from 'fs-extra';
-import { readdir, rename, stat, writeFile } from 'fs/promises';
+import { readdir, stat, writeFile } from 'fs/promises';
 import { promisify } from 'util';
 import { execFile } from 'child_process';
 import { join, normalize, extname } from 'path';
@@ -42,7 +42,7 @@ import type { SettingsChannel } from '../main/settingsChannel';
 
 import type { LoggerType } from '../types/Logging';
 import { getGotOptions } from './got';
-import { checkIntegrity } from './util';
+import { checkIntegrity, gracefulRename } from './util';
 import type { PrepareDownloadResultType as DifferentialDownloadDataType } from './differential';
 import {
   prepareDownload as prepareDifferentialDownload,
@@ -99,6 +99,8 @@ export abstract class Updater {
 
   private activeDownload: Promise<boolean> | undefined;
 
+  private markedCannotUpdate = false;
+
   constructor(
     protected readonly logger: LoggerType,
     private readonly settingsChannel: SettingsChannel,
@@ -156,6 +158,29 @@ export abstract class Updater {
     ipcMain.handleOnce('start-update', performUpdateCallback);
   }
 
+  protected markCannotUpdate(
+    error: Error,
+    dialogType = DialogType.Cannot_Update
+  ): void {
+    if (this.markedCannotUpdate) {
+      this.logger.warn(
+        'updater/markCannotUpdate: already marked',
+        Errors.toLogFormat(error)
+      );
+      return;
+    }
+    this.markedCannotUpdate = true;
+
+    this.logger.error(
+      'updater/markCannotUpdate: marking due to error: ' +
+        `${Errors.toLogFormat(error)}, ` +
+        `dialogType: ${dialogType}`
+    );
+
+    const mainWindow = this.getMainWindow();
+    mainWindow?.webContents.send('show-update-dialog', dialogType);
+  }
+
   //
   // Private methods
   //
@@ -243,6 +268,7 @@ export abstract class Updater {
       return true;
     } catch (error) {
       logger.error(`downloadAndInstall: ${Errors.toLogFormat(error)}`);
+      this.markCannotUpdate(error);
       throw error;
     }
   }
@@ -450,6 +476,9 @@ export abstract class Updater {
     const tempUpdatePath = join(tempDir, fileName);
     const tempBlockMapPath = join(tempDir, blockMapFileName);
 
+    // If true - we will attempt to install from a temporary directory.
+    let tempPathFailover = false;
+
     try {
       validatePath(cacheDir, targetUpdatePath);
 
@@ -491,7 +520,7 @@ export abstract class Updater {
 
           // Move file into downloads directory
           try {
-            await rename(targetUpdatePath, tempUpdatePath);
+            await gracefulRename(this.logger, targetUpdatePath, tempUpdatePath);
             gotUpdate = true;
           } catch (error) {
             this.logger.error(
@@ -561,16 +590,28 @@ export abstract class Updater {
 
       // Backup old files
       const restoreDir = await getTempDir();
-      await rename(cacheDir, restoreDir);
+      await gracefulRename(this.logger, cacheDir, restoreDir);
 
       // Move the files into the final position
       try {
-        await rename(tempDir, cacheDir);
+        await gracefulRename(this.logger, tempDir, cacheDir);
       } catch (error) {
-        // Attempt to restore old files
-        await rename(restoreDir, cacheDir);
+        try {
+          // Attempt to restore old files
+          await gracefulRename(this.logger, restoreDir, cacheDir);
+        } catch (restoreError) {
+          this.logger.warn(
+            'downloadUpdate: Failed to restore from backup folder, ignoring',
+            Errors.toLogFormat(restoreError)
+          );
+        }
 
-        throw error;
+        this.logger.warn(
+          'downloadUpdate: running update from a temporary folder due to error',
+          Errors.toLogFormat(error)
+        );
+        tempPathFailover = true;
+        return { updateFilePath: tempUpdatePath, signature };
       }
 
       try {
@@ -584,7 +625,9 @@ export abstract class Updater {
 
       return { updateFilePath: targetUpdatePath, signature };
     } finally {
-      await deleteTempDir(tempDir);
+      if (!tempPathFailover) {
+        await deleteTempDir(tempDir);
+      }
     }
   }
 
diff --git a/ts/updater/macos.ts b/ts/updater/macos.ts
index 678ea2286..fefbfc9b7 100644
--- a/ts/updater/macos.ts
+++ b/ts/updater/macos.ts
@@ -29,26 +29,12 @@ export class MacOSUpdater extends Updater {
     } catch (error) {
       const readOnly = 'Cannot update while running on a read-only volume';
       const message: string = error.message || '';
-      const mainWindow = this.getMainWindow();
-      if (mainWindow && message.includes(readOnly)) {
-        logger.info('downloadAndInstall: showing read-only dialog...');
-        mainWindow.webContents.send(
-          'show-update-dialog',
-          DialogType.MacOS_Read_Only
-        );
-      } else if (mainWindow) {
-        logger.info(
-          'downloadAndInstall: showing general update failure dialog...'
-        );
-        mainWindow.webContents.send(
-          'show-update-dialog',
-          DialogType.Cannot_Update
-        );
-      } else {
-        logger.warn(
-          'downloadAndInstall: no mainWindow, cannot show update dialog'
-        );
-      }
+      this.markCannotUpdate(
+        error,
+        message.includes(readOnly)
+          ? DialogType.MacOS_Read_Only
+          : DialogType.Cannot_Update
+      );
 
       throw error;
     }
diff --git a/ts/updater/util.ts b/ts/updater/util.ts
index b1b038e34..5bff132ea 100644
--- a/ts/updater/util.ts
+++ b/ts/updater/util.ts
@@ -2,10 +2,15 @@
 // SPDX-License-Identifier: AGPL-3.0-only
 
 import { createReadStream } from 'fs';
+import { rename } from 'fs/promises';
 import { pipeline } from 'stream/promises';
 import { createHash } from 'crypto';
 
 import * as Errors from '../types/errors';
+import type { LoggerType } from '../types/Logging';
+import * as durations from '../util/durations';
+import { isOlderThan } from '../util/timestamp';
+import { sleep } from '../util/sleep';
 
 export type CheckIntegrityResultType = Readonly<
   | {
@@ -42,3 +47,76 @@ export async function checkIntegrity(
     };
   }
 }
+
+async function doGracefulRename({
+  logger,
+  fromPath,
+  toPath,
+  startedAt,
+  retryCount,
+  retryAfter = 5 * durations.SECOND,
+  timeout = 5 * durations.MINUTE,
+}: {
+  logger: LoggerType;
+  fromPath: string;
+  toPath: string;
+  startedAt: number;
+  retryCount: number;
+  retryAfter?: number;
+  timeout?: number;
+}): Promise<void> {
+  try {
+    await rename(fromPath, toPath);
+
+    if (retryCount !== 0) {
+      logger.info(
+        `gracefulRename: succeeded after ${retryCount} retries, renamed ` +
+          `${fromPath} to ${toPath}`
+      );
+    }
+  } catch (error) {
+    if (error.code !== 'EACCESS' && error.code !== 'EPERM') {
+      throw error;
+    }
+
+    if (isOlderThan(startedAt, timeout)) {
+      logger.warn(
+        'gracefulRename: timed out while retrying renaming ' +
+          `${fromPath} to ${toPath}`
+      );
+      throw error;
+    }
+
+    logger.warn(
+      `gracefulRename: got ${error.code} when renaming ` +
+        `${fromPath} to ${toPath}, retrying in one second. ` +
+        `(retryCount=${retryCount})`
+    );
+
+    await sleep(retryAfter);
+
+    return doGracefulRename({
+      logger,
+      fromPath,
+      toPath,
+      startedAt,
+      retryCount: retryCount + 1,
+      retryAfter,
+      timeout,
+    });
+  }
+}
+
+export async function gracefulRename(
+  logger: LoggerType,
+  fromPath: string,
+  toPath: string
+): Promise<void> {
+  return doGracefulRename({
+    logger,
+    fromPath,
+    toPath,
+    startedAt: Date.now(),
+    retryCount: 0,
+  });
+}
diff --git a/ts/updater/windows.ts b/ts/updater/windows.ts
index 9b0aac477..bfdb2e52d 100644
--- a/ts/updater/windows.ts
+++ b/ts/updater/windows.ts
@@ -11,7 +11,6 @@ import pify from 'pify';
 
 import { Updater } from './common';
 import { markShouldQuit } from '../../app/window_state';
-import { DialogType } from '../types/Dialogs';
 
 const readdir = pify(readdirCallback);
 const unlink = pify(unlinkCallback);
@@ -54,18 +53,7 @@ export class WindowsUpdater extends Updater {
         await this.install(updateFilePath);
         this.installing = true;
       } catch (error) {
-        const mainWindow = this.getMainWindow();
-        if (mainWindow) {
-          logger.info(
-            'createUpdater: showing general update failure dialog...'
-          );
-          mainWindow.webContents.send(
-            'show-update-dialog',
-            DialogType.Cannot_Update
-          );
-        } else {
-          logger.warn('createUpdater: no mainWindow, just failing over...');
-        }
+        this.markCannotUpdate(error);
 
         throw error;
       }