Automation and Attachments

Hello!

I am working on some workflows and one of them is to send a notification when a document is sent out. Cool, easy, not a problem. If this box is filled with this AND an attachment is added, send a notification. My question is if multiple attachments are added before the box is filled (over time, not at once) will that notification, once conditions are met, send out ALL of the attachments or is there a way to choose which attachments get added? I think I already know the answer to this but figured I'd ask in case I missed something!

(For help, this is the information I was sent) - So I was going to work on the workflow to send the attachment out... but is there a way so it Only sends the attachment for the password sheet? I'm worried that it will send any attachment added to the sheet. The workflow to send it out to hiring managers, so when the document is added the only option I see is to send the attachment but no way to choose which attachments to send or if it sends all attachments on the row.