You are prompted to sign in repeatedly
Once you have signed into the Hub, CloudFiler shouldn't require you to sign in again unless you have signed out or there is a significant update to the software, so if you find that the request to sign in is appearing every day or even more frequently, the problem is likely to be Windows failing to cache the token correctly.
You can force it to do this by signing into Microsoft 365 in a browser.
So visit http://www.outlook.com/ and sign in. This will kick their services into life, then sign into the CloudFiler Hub and it should cease asking you to sign in repeatedly.