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Have you noticed that sometimes Drag and Drop works to upload files and sometimes it does not?
Note that you can drag and drop a file that has been saved on your computer or the shared drive. You cannot drag and drop directly from Outlook. This is not specific to CR-Insight®. You must first save the MSG file (or any file type) prior to dragging and dropping to any web based solution (IE Gmail, Dropbox, etc)
Yes, attached files will be there when you save a .msg file
Although you cannot drag and drop from Outlook to the add document screen, you CAN drag and drop an email from Outlook directly into the file selection window. See below for steps on this: