How to Fix Upgrade to iCloud for Windows Failed Error: 6 Best Proven Methods


In this guide, we will discover: How to Fix Upgrade to iCloud for Windows Failed Error: 6 Best Proven Methods – Easy Beginners Guide

The iCloud for Windows upgrade failed for the latest version and subsequently, error 101 has been showing up as well. If you’re also facing the same issue, keep reading.

Apple did a great job publishing a Windows PC app for iCloud storage. Just like you access the iCloud content on a Mac, iPhone, or iPad, do the same on a Windows 11 or Windows 10 PC.

The app automatically syncs the content of your iCloud account like iCloud Drive, Contacts and Calendars, Photos, etc., to dedicated local drive folders on your Windows 11 PC. That’s not all! The tool can securely sync all your passwords and bookmarks on Safari on macOS with Windows 11 apps like Microsoft Edge, Google Chrome, and Mozilla Firefox.

However, there has been an ongoing issue with the iCloud for Windows app. It prevents your Windows PC’s iCloud copy from updating itself. This is a serious security issue and you must pay close attention to it.

Read the article until the end to know more about this error, and some proven methods to fix iCloud updates so you can keep your cloud data safe.

Also read: How To Clear iCloud Storage

What Is the iCloud for Windows Upgrade Error 101?

A few days back, I was playing around with the iTunes for Windows app and suddenly got a notification that I could also install iCloud for free. I installed the app and signed in to iCloud storage using my Apple ID. I could see that the app was syncing files to the local drive from iCloud.

However, after 10 to 15 minutes, I got the following warning:

Upgrade to iCloud for Windows 14.1 failed. Please reboot and try again (Error 101)

I followed the instructions from the iCloud warning and restarted my Windows 11 PC. I launched the app again and it seemed everything was fine for a while. Again, after a few minutes, I saw the same problem.

I did some research online and learned that this is a pretty common error for the iCloud app on Windows 10 and 11 operating systems. The issue surfaces when you download and install an earlier version of the iCloud for Windows app than the latest one which is on the Apple servers.

Also read: Renaming Image Files on iCloud

Why Do You Need to Fix iCloud Upgrade Error 101?

Apple releases frequent updates for all of its apps, including the Windows iCloud app. Updates keep your app safe and secure from known security vulnerabilities. Since the iCloud for Windows app creates a direct data link between your data on the Apple Servers and your Windows 11 PC, it’s important that you keep the iCloud app up-to-date.

If you ignore the upgrade error for a long time and a hacker finds a way into your Apple cloud storage using an outdated iCloud app on your Windows PC, then your privacy is at risk. Also, if you’re unable to update the iCloud app to its next version, Apple might revoke your Windows PC’s access to its cloud data using an outdated app.

Also read: How to Show or Hide iCloud Music in iTunes

How to Fix Upgrade to iCloud for Windows Failed (Error 101)

From many threads on tech-related communities like Apple Discussions and Microsoft Answers, it’s clear that iCloud on Windows users is still facing the error. Looks like Apple and Microsoft tech community moderators aren’t prioritizing the issue yet.

Updating iCloud for Windows app after resolving the Error 101 issue

However, I’ve tried a few troubleshooting, and it looks like I was able to upgrade my iCloud app to the latest 14.1 version. Find below the troubleshooting steps I tried and got a remedy to the above situation:

1. Unblock iCloud From Windows Firewall

Since iCloud needs access to the internet to download updates, it must be whitelisted on your Windows Defender Firewall. As soon as you install a new app, the Windows Defender Firewall pops up to ask for approval to let new apps access the internet. If you somehow missed that pop-up for the iCloud app, you’ll see the update error. Here’s how you can fix this:

  • Open the Windows Settings app by pressing Windows + I together.
  • Click the Privacy & security option on the left-side navigation pane.
  • Select Windows Security on the right side menu of the Settings app.
Firewall & network protection
Firewall & network protection
  • Under the Protection areas section, you should see Firewall & network protection. Click on that.
  • When on the Firewall & network protection utility, click the Allow an app through firewall hyperlink.
Allow apps on Windows Defender Firewall
Allow apps on Windows Defender Firewall
  • The Allowed Apps dialog box will pop up. Click on the Change settings button.
  • Scroll down the list until you find iCloud.
  • Checkmark the checkbox to the left of the iCloud app entry.
  • Ensure you checkmark network access for Private and Public networks.
  • Click OK to save the changes.

Open the iCloud app again and this time it should upgrade to the latest edition.

If the above trick didn’t work for you, try the following approaches to fix the “Upgrade to iCloud for Windows Failed” error:

2. Tweak a Few iCloud Advanced Options

You can access the advanced app settings on the Windows 11 Settings app to optimize iCloud so it can upgrade to the next version. Here’s how:

  • Click the Start button and type Apps.
  • Select Add or remove programs tool from the search results.
  • Scroll down to find the iCloud app.
Advanced options for iCloud
Advanced options for iCloud
  • Once found, click the ellipses icon on the right end and select Advanced options.
Advanced app options optimization for iCloud
Advanced app options optimization for iCloud
  • Now, make the following changes:
    • Background apps permissions: Always
    • Runs at log-in: Enable all like iCloud Drive, iCloud Photos, etc.
How to terminate iCloud
How to terminate iCloud
  • Once done, click the Terminate button on the same window.
  • This would force stop the existing iCloud process on the Task Manager.
  • Restart iCloud from the Start menu or Windows Desktop and see if the issue comes back or not.

3. Repair the iCloud App Installation

You can also try the built-in Windows app repair tool to attempt to repair the iCloud installation. Here’s how it’s done:

  • Hit Windows + I and select Apps on the left-side panel.
  • Select Installed apps on the right-side list of items.
  • Scroll down to find the iCloud app.
  • Click the kebab or three dots menu on the right and choose Advanced options.
How to Repair and Reset iCloud
How to Repair and Reset iCloud
  • Scroll to the Reset section and hit the Repair button.

Test the app after the repair process. It’s likely that the app would be able to upgrade to the latest edition. If it doesn’t click the Reset button just below the Repair button. You’ll lose all synced content on the Windows 11 PC from iCloud if you reset the app.

4. Update Windows OS

Your Windows 10 or 11 OS must have the latest security patches and feature updates so that iCloud can function. So, follow these steps to update the Windows installation:

  • Go to Windows Update from the Settings (Windows + I) app.
Update Windows 11 to fix Error 101 on iCloud for Windows app
Update Windows 11 to fix Error 101 on iCloud for Windows app
  • Hit the Check for updates button.
  • When the system discovers new security or features updates, click the Download and Install button.
  • Sometimes, long-due updates might start downloading automatically.
  • Wait for the Windows update task to complete, restart the PC, and test iCloud again.

5. Install iCloud From Microsoft Store

If you installed iCloud on Windows a few years back by downloading an installer from Apple, you must uninstall that copy. Then, re-install the app from Microsoft Store. Here’s how:

  • Click the Start menu and type iCloud.
  • Select Uninstall at the bottom of the Start menu search page.
  • When the uninstallation is complete, launch the Microsoft Store app.
  • Type iCloud in the search box and hit Enter.
iCloud download from Microsoft Store
iCloud download from Microsoft Store to fix Upgrade to iCloud for Windows Failed issue
  • When the iCloud app appears, click the Install button.
  • Microsoft Store will download and install the app automatically.
  • Click Open to launch iCloud on Windows 11 or 10 PCs.

6. Install iCloud From an Installation Package

Alternatively, if you installed the iCloud app from the Microsoft Store and experienced the “Upgrade to iCloud for Windows Failed” issue, you can switch to the package installer for iCloud. At the time of writing, Apple removed the link to the standalone installer for iCloud on Windows.

You can download the app, at your own discretion, from the following third-party software hosting websites:

You might also want to check out this r/iCloud thread on Reddit to find direct links to download the iCloud installation package from Apple’s servers.

Don’t forget to uninstall the existing Microsoft Store iCloud from your Windows 11/10 PC before installing the non-Microsoft Store iCloud app.


As of now, these are all the troubleshooting methods you can follow to fix the iCloud upgrade (Error 101) issue on Windows 10 and 11 PCs. Try the fixing methods in the order they appear to avoid trying all of these. If you know any other better solution to the above issue, don’t forget to comment below.

Next up, how to delete apps from iCloud in easy ways.


is Senior Writer DZ-TECH, where he covers the world of technology, hacking, cybersecurity, surveillance and privacy.

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