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 ... View more

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Running a business shouldn’t feel like a guessing game — which includes preparing for the year ahead. Square polled business owners on the trends they expect to shape 2026, and this webinar dives deep  into the signals that matter.    Join us to hear the moves operators across industries are making now — and the shifts they’re preparing for in 2026.   What you’ll learn: Industry predictions across food and beverage, retail, beauty, and professional services How business owners are adapting to economic shifts and evolving consumer behavior How AI, automation, and other tech can help you manage costs, attract customers, and grow Speakers: Ryan Cole, CEO/Partner, Hi Neighbor Hospitality Group René de la Garza, Founder of Brow Down Studio and Brow Down Studio Pro Matt Kochanowski, Product Marketing Lead, Square Register now — see you there! ... View more

Sharing our next live webinar, Emerging 2026 trends: Insights and predictions from local business owners, here. Hope you can tune in!   Please register at the link here if you're able to join. See you there. 😎 ... View more

Sharing our next live webinar, Emerging 2026 trends: Insights and predictions from local business owners, here. Hope you can tune in!   Please register at the link here if you're able to join. See you there. 😎 ... View more