Square Terminal not recognizing existing Customer Emails?

[akramer]

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. Or, I have to go into the sale post-transaction and make a manual connection to the customer. 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

[kacey_k]

As a Square Champion, I totally get why this feels frustrating — and you’re not a dunce, nor are you missing a hidden toggle. What you’re running into is actually an intentional privacy + consent design choice on Square’s side, not a bug or plan limitation.

Here’s the plain-English explanation:

Square cannot automatically link a card, receipt email, or past transaction to an existing customer profile unless the customer explicitly provides their email at the time of that transaction or is selected from the Customer Directory during checkout. Even if:

• It’s the same card
• The same receipt email
• The same person
• The same day

Square treats each transaction as anonymous by default unless consent is actively captured again.

Why? Two big reasons:

1. Data privacy & compliance (especially around email marketing laws). Square avoids assuming identity or marketing consent based on payment credentials alone.
2. Shared cards & edge cases (family cards, business cards, gifts, etc.) — Square won’t auto-merge identities without explicit input.

So unfortunately, there is no setting in Square Online Plus or Square for Retail that changes this behavior today.

What 

does

 help (practical workarounds):

• Selecting the customer from the Customer Directory before taking payment (best option when possible).
• Leaving email receipts ON, so customers are prompted naturally.
• Using the post-transaction “Add customer” flow (which you’re already doing).
• For events/festivals: a QR code or sign at checkout prompting customers to confirm email for rewards/receipts helps reduce re-asking verbally.

You’re also correct that Square for Retail does not change this specific behavior — it adds inventory and reporting depth, but customer-matching rules remain the same.

You’re asking a very common and valid question, and this exact feedback has been shared internally many times by Champions and sellers alike. Hopefully we’ll see smarter matching options in the future — but for now, what you’re experiencing is expected behavior, not user error.

You’re not crazy — you’re just running into the limits of how Square protects customer consent.