Windows 10’s October 2018 Update has more bugs. Microsoft won’t offer the update if you have iCloud installed, and Apple won’t let you install iCloud if you’ve already upgraded. You’ll also have trouble if you have F5 VPN software installed.
This information comes from Microsoft’s own Windows 10 Update History page, where Microsoft is publicly tracking the October Update’s bugs.
According to Microsoft, Apple iCloud version 184.108.40.206 has an incompatibility with the latest update. You’ll have trouble updating or synchronizing Shared Albums after upgrading. If you try installing iCloud on the October Update, you’ll see an error message saying “iCloud for Windows requires Windows 7, Windows 8, or Windows 10 (April 2018 Update) and earlier.”
Windows Update won’t offer you the October 2018 Update if you have Apple iCloud installed. In other words, Microsoft has placed an “upgrade block” on systems with iCloud installed.
If you have iCloud installed, Microsoft recommends you not upgrade to the October 2018 Update with the downloadable Update Assistant tool. You’ll have to deal with the buggy iCloud behavior if you bypass the block and upgrade anyway. iCloud users who clicked “Check for Updates” near the beginning of October are presumably dealing with this bug right now, too. Thanks, Microsoft.
Microsoft says it’s working with Apple to make a future version of iCloud compatible.
Microsoft’s website also says that systems with F5 VPN clients installed “may lose network connectivity when the VPN service is in a split tunnel configuration.” If you’ve upgraded to the October 2018 Update and use this software, you can force all system traffic through the tunnel to solve this problem.
Once again, Microsoft has put an “upgrade block” in place to prevent Windows Update from updating systems with an F5 VPN installed. Microsoft is working on a fix to this problem.
Systems with Trend Micro OfficeScan or Worry-Free Business Security also have upgrade blocks in place at the moment, as do systems with AMD Radeon HD2000 and HD4000 series GPUs. Mapped network drives are also broken, but systems with mapped network drives will automatically install the update.