Multiple Documents signed by the same person?

Hi all,

I am trying to send multiple documents- hopefully in the same go- to ONE person. Each document needs to be signed individually by the same person. I have seen that there is a Batch Send option where you can send one document to multiple people- like the same standard contract to every employee. But I am trying to do the opposite of that. Each page I send needs to be signed by the same person. 

I managed to send a test out with 7 documents to the same email address by configuring and tediously re-adding the same email address to the designated signers and then assigning the different "profiles" to each signature. However, when I went to my email to try to sign them, none of the signature boxes I had added to the documents showed up. When I tried to re-send the documents and followed the same exact procedure, it now goes back to saying that I cannot have the same email address multiple times on the same signing order. 

So does that just mean you actually have to send every single document out individually? There is a support page on here that says Box Sign only supports one page being sent out to one email but 1) I have received multiple documents before (but I only had to sign one signature field) and 2) that support page hasn't been updated since 2023 ://///)

What about contracts where there are multiple signatures needed on each page? Surely you can somehow do that. I feel dumb for having to come in and ask this but I actually haven't been able anything helpful about this! 

Additionally- why won't the signature fields show up on the pages? I have had a document sent to me before where the signature field did not show up on the document and I saw the person who sent it to me fill out their whole template with field boxes. ??

Thanks for any help you can offer!!