Inability to Use "Send File as Attachment" in Outlook Inability to Use "Send File as Attachment" in Outlook Issue: Acrobat users cannot use other Outlook windows when the "Send File as Attachment" feature is active. Workaround: After sending a file via Outlook, close the draft email window manually, or use the web-based Outlook application if the desktop version continues to cause issues. In a new email go to Adobe Acrobat ribbon under Message tab, and select settings and then "Never prompt while attaching" this will stop it automatically sending attachments using Adobe Cloud Storage.