Collecting customer emails; Square not recognizing existing customers?

I searched the Community for this topic and there are LOTS of threads about collecting customer emails, but nearly all are archived -- so I'm starting this one fresh. I use Square Terminal when I conduct POS transactions at festivals and art shows, and I have a decent number of repeat customers at those events. I understand that Square won't reveal a customer email address that has NOT been provided directly to me, so I end up having to ask for it ("would you like to join my mailing list?") and adding them at the email marketing prompt at checkout. 

 

HOWEVER: If a customer *has* shopped with me before, is on my email list, has just made yet another transaction (sometimes even later that same day or the next day), all using the same credit card and contact/email receipt information.... WHY can't Square recognize that the customer exists and connect them to the sale? Square apparently doesn't recognize them in any way. In order for me to keep customer sales history records, when a customer makes an additional transaction and becomes (or continues to be) a repeat customer, I have to *manually* attach the sale to this person by yet AGAIN asking them for their email address, and typing it into the field at the marketing prompt. Why?!??!! 

 

I really want someone to tell me that I am a dunce and I just need to toggle something on or off to make this connection start working. For what it's worth, I have the Square Online Plus plan. I hear lots of folks talk about Square for Retail, though from what I've read in the Square documentation (see link), it wouldn't make any difference. I'd love to be wrong about that.

 

https://squareup.com/help/us/en/article/5976-get-started-with-email-collection-tools

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Square Champion

I believe that when your guest checks out, you should have the option for them to request a receipt and receive it via text or email. Also thought that if a guests uses their card once on your device and left contact info, that it would automatically populate from then on. All of this info can be collected and used for marketing purposes. Also Square has their loyalty program that will allow you to collect that data prior to check out. 

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