We have a solution which uploads to a SharePoint list.
Users have a 2 way process where they attach attachments with the same name, but with in different attachment elements. In this case on the next step (where both attachments are displayed) we see only one of them, and in request item there's also only one of attachment. The system sees them as one the same happens also if these attachments has different sizes. The type of attachments is also the same.
This is a designed behavior as all the form attachments are added to a form list item in SharePoint
and SharePoint does not allow duplicate attachments.
As a workaround, you can use rename attachment plugin add attachment to the activity and then rename these attachments.