Hi @swarr18 

Are you sending from the Invoices screen? If you are then you can only send one email at a time. 

@kbeatty21 yes the invoices screen but its not multi invoices, it is stuff under the files tab, currently we have to manually drag them into the email and it sends 2 attachments. I am trying to see if there is a way that it auto pulls the files into the email

Currently it does not appear to be another way. Drag and drop is the only one I have found as well.