Alerts Not Sending Even if Adding an Attachment is the Trigger

I'm trying to create an alert so that when someone attaches a file to a row, the attachment and row information gets sent to someone else, but I can't seem to get it to work. Here's the workflow set-up:

I DO get an alert if a new row is added with an attachment, but I need an alert for a row that already exists.

I DO get an alert when the action is "Request and Update" or "Request an Approval," but the email doesn't include the attachment.

I've tried adding other cell changes in addition to adding an attachment (like checking a box), adding a condition, but nothing seems to work.

Does anyone have a solution?