Here is how you can do it. Object OutgoingEmail should have multiple-allowed attribute Attachments of type Attachment. Object Attachment has attributes Doc of type Document and calculated attribute OrderNumber of type number. Attribute Doc would hold a file. Attribute OrderNumber can be set with a rule like this:
Attachment.OrderNumber = COUNT Attachment WHERE (Attachment.ID <= ThisAttachment.ID AND Attachment.Email = ThisAttachment.Email) + 1
You could then add rules to notification OutboundEmail to initialize each of its Attachment attributes, for example:
FIND Attachment WHERE Attachment IN OutboundEmail.OutgoingEmail.Attachments AND Attachment.OrderNumber = 1
OutboundEmail.Attachment1 = Attachment.Doc
FIND Attachment WHERE Attachment IN OutboundEmail.OutgoingEmail.Attachments AND Attachment.OrderNumber = 2
OutboundEmail.Attachment2 = Attachment.Doc
...
Each initialization rule should be entered as a separate rule to OutboundEmail.
You would also need to add the following rule to object OutgoingEmail to ensure there are no gaps in attachment numbers when an attachment is removed from the list:
If Attachment WAS REMOVED FROM OutgoingEmail.Attachments Then
FIND Attachment WHERE Attachment IN OutgoingEmail.Attachments
UPDATE Attachment