I am using Outlook 2007 with POP/SMTP settings to connect to Gmail. I have the button checked to delete messages from the server when deleted from deleted items. However the messages are still there when I log into Gmail online. Does anyone know a reason why this maybe happening? Many thanks. When I delete them from Gmail they go as usual. The whole point of using Outlook is to not have to delete from Gmail manually. BTW the box is ticked to delete from server.