Hey there sodenelj,
Welcome to Apple Support Communities.
It sounds like you're running into an issue updating iCloud for Windows on your PC. What is the exact alert message that you see when the issue occurs?
The alert that you're seeing may be appearing because iCloud for Windows doesn't currently support Outlook 2016, as mentioned in the article below.
Get help using Outlook with iCloud for Windows - Apple Support
iCloud for Windows currently supports Outlook 2007 through Outlook 2013. Support for Outlook 2016 will be available in an update to iCloud for Windows in December. Until then, if you use Outlook 2016, you can access iCloud Mail, Contacts, and Calendars on iCloud.com.
Ciao.