Windows 10 October Update Breaks iCloud, F5 VPN

John Lister's picture

Some users of Apple's iCloud software will be unable to get the latest Windows 10 update right now. It's an example of Microsoft blocking the update rather than causing problems with specific applications.

iCloud is the online backup and sync tool for Apple devices such as iPhones and iPads. It's aimed at people who have iOS mobile devices but also use a Windows PC. iCloud lets users access Apple services and data such as their email, photos and calendar on both the mobile device and computer.

Unfortunately iCloud is the victim of yet another glitch in the October update of Windows 10, one of the two major updates each year. After the update started rolling out, users reported problems with a feature that lets people share access to online photo albums.

Updates Put On Hold

It appears the problem is caused by an incompatibility that slipped through the cracks because both Windows and iCloud were getting updates at a similar time.

How individual users are affected for now depends on what's already happened. If they haven't (successfully) installed the Windows 10 October update, that will be put on hold until the glitch is fixed. It appears this will happen even if the user actively tries to install the update, though Microsoft has advised users not to do this. (Source:

If users have already got the October update, then they won't be able to update iCloud for the moment.

Apple and Microsoft are now working together to produce a version of iCloud that works with the updated Windows 10.

VPN Software Also Glitched

It's not the only software compatibility glitch with Windows 10. There's also a problem for users of a virtual private network (VPN) service from a company called F5.

A VPN is a tool that keeps Internet traffic completely hidden from third parties, a little like switching from a glass tube to a concrete tunnel. It's commonly used by people who want to keep their online activity hidden or get around geographic blocks that stop them watching video content such as streaming services.

As with the iCloud issue, if Microsoft spots somebody with the F5 VPN installed, it's holding off the automatic Windows 10 update until there's a fix. (Source:

What's Your Opinion?

Is Microsoft right to hold off the Windows 10 update if it knows it will cause a problem with a specific application? Or is it more important to update Windows rather than worry about a single piece of software? Should Microsoft do more to work with software companies on avoiding such glitches?

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alan.cameron_4852's picture

I feel that Microsoft made a big mistake when it let go so many testers from the Windows 10 project.
They need to start re-hiring them and get back on top of the problems. They are losing the confidence of the business community as well as the consumers.
More testing is definitely needed.

sirpaultoo's picture

Easy solution: go back to unforced updates. Even before MS started using rollups - when the bad update was easy to identify (and avoid).
There's something not right when my unpatched version of XP is working better than my patched version of Win10.

kitekrazy's picture

Not surprised that Windows updates screw up some type of networking. They need to fire some developers.