ContributionsMost RecentMost LikesSolutionsRe: Outlook 2016 continually prompts for username and password constantly and will not sync I've been seeing the same issue on Outlook 2010 and 2016 for some months. It seems to have gotten worse lately. I've changed passwords, based on the original suggestions. I only seem to see the problem on the Cox account, one of 3 that I use regularly. Is there anything to the speculation about timeout settings on the Cox servers being part of the problem. I've seen the problem on multiple computers. I don't see it on iPhone, iPad. I don't use webmail frequently; so, I'm not sure if it occurrs or not. The problem is very annoying.