Help in this issue would be greatly appriciated. I recently moved a client onto the company domain and copied his mail over to an exchange account. I activated Outlook anywhere with basic authentication and installed the Godaddy certificate via IE (32bit as administrator) under trusted root folder. Now every time he opens his outlook out of the office he gets the error I have attached. Another problem I have found and I do not know if this is a bug but, should I untick "Connect to Microsoft Exchange" he still gets prompted for a username and password. After further investigation I found "Connect to Microsoft Exchange" to be ticked again. He is using Outlook 2007 on exchange 2007 on a SBS 2008 Server. The other domain users don't seem to have the same error (see attached). The user having the problem can receive email when dismissing the error.