Get outlook mail message - choose one mail between two identical mails - one contains a file and the other one does not

Hello @omri_Yakobovich ,

As per the logic you are trying to send 2 emails, Files were downloaded and File were not found.
Also you have mentioned you created 2 emails, one with atatchment and another without attachment. So i think the mails triggered as per the logic.

If you want to check the files with attachment and without atatchment you can write as below.
Item.Attachments.Any

Also refer the below post.