Adding the same person as a signer multiple times

We have several agreements that require multiple signatures. In many cases the same person will need to sign at several different stages.

A simple example woule be: A request form may be signed by person A confirming their request, signed by person B approving the request, and then signed again by person A confirming they actioned their own request (this happens often).

When I add the recipients to do this like in the screenshot, it does not behave as I would expect.

I sign the agreement and it is sent to the 2nd recepient.
They sign the agreement. Everything as normal so far.

What happens then, is I get an email saying I need to sign a document but it does not seem to recognise that it is me. When I click the link in the email to sign the document it does not let me use my usual signature but instead it asks me to type my name or draw a new signature, this is a tad annoying but also a bit of an odd UX. Moreover, if I log in to my portal there is nothing in the "waiting for you" section.

I assume this is by design for some reason, so my question is, does anyone know how do I correctly send an agreement to the same person multiple times and it appear in their "waiting for you" section no matter how man times they've signed the agreement before.