How to fix "Upgrade to iCloud for Windows failed" error in Windows?

iCloud for Windows lets users keep the Apple services, including photos, contacts, and calendars, in sync with the Windows PC. Unfortunately, not all users have been able to install or update iCloud for Windows without errors: “Upgrade to iCloud for Windows failed”. Sometimes, the messages will read, “Please reboot and try again”, while at other times, specific error codes may appear, like Error 101.

It can be installed for quite a few reasons: conflicts with the installed software, outdated system components, or corrupted installation files. Often, the installed versions of Microsoft Visual C Redistributable might interfere with the installation. Additionally, third-party security software or settings of a firewall may interfere with installing the bundle and thus producing the “Upgrade to iCloud for Windows failed” error.

There are some ways to fix the problem for the users. Checking for issues with permissions, and running the iCloud installer as an administrator can help to avoid such problems. Updating system components, including the Microsoft Visual C Redistributable, is required in order to support the latest version of iCloud.

Disabling antivirus or temporarily adjusting firewall settings might also permit installation without interference. Steps that may also work to sort out this “Upgrade to iCloud for Windows failed” error include uninstalling the currently used iCloud version and reinstalling it cleanly.

Automatically, in such cases, use a trustworthy FortectMac Washing Machine X9 repair utility tool that may help to track and resolve system conflict issues that could be interfering with the attempt to install or upgrade iCloud for Windows.

Fix 1. Run the installer as administrator

Running the iCloud installer with elevated privileges can resolve permission-related issues that prevent the installation or upgrade from completing.

• Right-click on the iCloud installer file.
• Select Run as administrator and follow the on-screen prompts to install.

Fix 2. Check for pending Windows updates

Outdated system components can interfere with the installation of iCloud for Windows. Ensuring that your system is up to date can resolve compatibility issues.

• Type Updates in Windows search and hit Enter.
• If updates are available, click Install updates.
• Otherwise, click Check for updates.
• If optional updates are available, install them as well.
• When all the update processes are complete, restart your device.

Fix 3. Disable third-party antivirus or firewall

Security software can sometimes block the installation process. Temporarily disabling it can help complete the iCloud upgrade.

• Open your antivirus application.
• Navigate to the settings and temporarily disable real-time protection.
• Turn off your firewall through the Control Panel under System and Security > Windows Defender Firewall > Turn Windows Defender Firewall on or off.
• Retry the iCloud installation.

Fix 4. Repair Microsoft Visual C Redistributable

An outdated or corrupted Visual C Redistributable can prevent the installation of iCloud for Windows.

• Right-click on Start and pick Apps & Features or Installed apps.
• Scroll down to find Microsoft Visual C Redistributables.
• Click each version or click three dots, select Modify, and choose Repair.
• If repairing doesn’t work, uninstall each version and download the latest ones from the official Microsoft website.
• Reinstall the redistributables and restart your computer.

Fix 5. Clear the iCloud installation files

Corrupted installation files can cause the “Upgrade to iCloud for Windows failed” error. Deleting temporary files may help.

• Press Win R, type %temp%, and press Enter.
• Delete all files in the Temp folder.
• Re-download the iCloud installer and try the installation again.

Fix 6. Uninstall and reinstall iCloud

Removing the existing version of iCloud and performing a clean installation can resolve conflicts from previous installations.

• Press Win I to open Settings and go to Apps/Installed apps.
• Locate iCloud, click on it, and select Uninstall.
• Restart your computer and download the latest version of iCloud from the official Apple website.
• Install the fresh version and check if the issue persists.

Fix 8. Verify Windows Installer service is running

Ensuring that the Windows Installer service is running properly can help complete the iCloud upgrade.

• Type Services in Windows search and press Enter.
• Scroll down to Windows Installer, right-click it, and select Start if it isn’t already running.
• Retry the iCloud installation.

Fix 9. Perform a clean boot

A clean boot starts Windows with minimal drivers and startup programs, which can prevent software conflicts during the iCloud installation.

• Type msconfig inWindows Search and press Enter to open the System Configuration window.
• Click on the Services tab and check the Hide all Microsoft Services box.
• Click Disable all to disable non-Microsoft services, then click the Startup tab.
• Open the Task Manager, disable all startup items, and close the Task Manager.
• Go to the Boot tab and mark the Safe boot option.
• Click OK on the System Configuration window and restart your computer.
• Restart your computer and try installing iCloud.

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