Outlook & iCloud: Your setup couldn't be started because the iCloud server stopped responding.

Windows 7 users are experiencing problems syncing Outlook with iCloud this week: iCloud stopped syncing Calendar & Contacts. When users sign out of iCloud and sign back in, they are presented with an error message when they try to enable Calendar & Contact sync. They may also receive an error message that the icloud drive has crashed or is not responding.

Your setup couldn't be started because the iCLoud server stopped responding.

The problem is caused by sites and services using TLS1.1 and TLS1.2 but Windows 7 is not offering them as default secure protocols in WinHTTP. Windows Server 2008 and 2012 are also affected by this update, but not windows 8 and 10.

The fix is simple: download and run the "Easy Fix" provided by Microsoft. It's about halfway down the page in this article: Update to enable TLS 1.1 and TLS 1.2 as default secure protocols in WinHTTP in Windows.

All Windows 7 (and Windows Server 2008/2012) users should run the Easy Fix, even if not affected by the iCloud issue. Other services will eventually be affected by the change to defaulting to TLS 1.n, including Office 365 Exchange online.