There have been several reports of Outlook repeatedly prompting for a password. When entering in your username and password, please use WESLEYAN\username in the username field. This should address the issue in the majority of cases.
If you have a problem where your Outlook is in Offline mode, please contact your Desktop Support person for assistance. They will be in touch with you as soon as possible to help resolve that issue. ITS is researching the cause of this issue.