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Can you have a party of 20 that wants separate checks and the computer still add on the 18% automatically?

Yes. The computer can track multiple checks issued to one party. It still adds up the total number of diners in that party.

I think a good hypothetical is meeting up with your buddies at a local sports bar for a fantasy baseball draft. People may sort of come and go and many separate checks may be issued. However, the servers are working the overall large party throughout.

When I think about it, the separate checks issue is actually probably a pretty good justification for the auto-added gratuity. I've been with groups of 10 before where almost everybody but me decided to stick the server when they were done. I felt awful and reached into my own pocket to try to make up at least some of the difference.

“I felt awful and reached into my own pocket to try to make up at least some of the difference.”

I used to do that when my BIL would buy dinner as he would leave a buck or something for an entire meal. After he became a cab driver he is a big tipper now!

When I think about it, the separate checks issue is actually probably a pretty good justification for the auto-added gratuity. I've been with groups of 10 before where almost everybody but me decided to stick the server when they were done. I felt awful and reached into my own pocket to try to make up at least some of the difference.

Yeah, I don't mind the auto-gratuity if a) the party is a big party and b) the service is good. Scratching out the auto-gratuity and then writing down Zero? Wow. And then later stating that she left $6? I don't buy it.