Are you using and iPad or Android? I would make sure you have the latest version of Square. Does this happen in any patteren like when you use the Contactless Chip reader, or Cash?
It sounds like your customers may have already used their payment card to make a purchase with a Square seller in the past. With Automatic Receipts, your customer's payment information is linked to their email address or phone number. This way, they won't have to enter their contact information each time.
Have your customers reported not receiving a receipt?
Jumping in here. There are times were the receipt automatically sends them a receipt without giving them the option of printing or texting. The system just bypasses the options screen leaving us both wondering what happen. I then have to go back to the main screen, to transactions and then print them a receipt.
You should be able to print receipts and order tickets immediately following a payment from the Square app on your iOS device so long as you have your printer set up for it.
We had the same issue with the receipt screen being totally bypassed sometimes (like 30% of the time) up until this spring when we found out that you could call in and have automatic receipts disabled per account (edit: we actually did it on the Square Beta facebook group and Howie did something to our account).
Now we don't have the issue anymore and it also solved the issue of customers spouses finding out about surprise purchases by the receipt being automatically sent.
In the app under settings / Signature & Receipt, there is a setting called Skip Receipt Screen. Make sure this is off. If it is on it will skip the screen for automatic receipt customers.
even with that turned option off it still would skip the receipt screen totally after some customers. and there didn't seem to be a rhyme or reason because some of the customers didn't even have email addresses entered for square, though most did.
