ContributionsMost RecentMost LikesSolutionsRe: Outlook client still prompting for password continuously I've been having the same problem for a week. Send/receive attempts work less than 30% of the time with no change to settings or PW. I've tried587 with TLS enabled & 465 with SSL - no change. I've had this problem in the past and it seems to eventually go away. Seems like a common recurring issue with Cox email for several years based on forum searches I did trying to find a solution. This is happening on my Outlook 2010 client on a Windows 10 PC as well as on a Gmail client on an Android tablet - both using a POP connection. No way that Cox can blame this on the email application. Both were working fine before. This significantly reduces productivity as well as being extremely annoying.