Besides ruining a perfectly good espresso shot, is there any reason not to pour a raw sugar in with the grinds? Some coffee shops do it and some won't. My thinking is that as long as the sugar is sandwiched in between the grinds and not actually touching the screen, it shouldn't cause any damage to our holy La Marzocco. Thoughts?

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My thought are the sugar would encourage channeling, and thus, ruining the shot.

Sugar aside. If the shot is ruined by the presence of sugar in the puck, it's not worth serving. If it weren't a cubano, you'd dump it down the drain.

Does it taste any different than espresso with sugar added?

Heck, making a simple syrup and pulling the shot into a bit might be a better idea.

Taste taste taste. Serve based on your own palate and reasoning.
This takes us to the ever-present conundrum of offering a customer what they want, and not what I think they should or should not be ordering. While I agree with you on the taste aspect and attempting to talk a customer out of ordering one, does running the shots with raw sugar cause any damage to the machine? This was the reasoning that I heard from one place.
I don't think it does. I once thought it did, but thinking it through was enough to prove otherwise.
Does it cost you more time and thus more money to clean the portafilter and screen before the next use? If so, could it be refused on that basis. Doesn't a business need to know where to draw the line between giving the customer what they want and doing what is best for the business? As long as you are pleasant and respectful to your customer about it I don't understand why a business must go beyond what is on their menu.
How do you handle other special requests that are not on the menu?
"Of course I can customize your drink for you!"
As long it's legal and we have the ingredients, we can do it. We live in a small town with a plethora of coffee shops, so we have to go out of our way to accommodate special requests.
The upside: we get to live in a beautiful place!
We live in a small town with a plethora of coffee shops, so we have to go out of our way to accommodate special requests.

I must disagree.

This mode of competition does not promote quality as the primary means of success, and you are competing based on who is willing to bend farther backwards.

While customers like customizations, they also like boundaries.
I strongly disagree with "sandwhiching" sugar inbetween grinds. I used to make cubanos on our GB5 about a year ago at my shop in California. We back flushed after EVERY cubano shot and I didn't notice any changes with shots (non-cubano) or any other problems. I find that the argument to this is also in part tied in with my thread on the "Splenda Scuffle." Personally, I don't mind Cubanos. I think they are tasty as a capp. I can't make them at my shop, so I stick to doppios =-D
How did you make the cubanos? Isn't sandwiching the sugar in between the grinds the only way to do it?
I've seen it as putting the grounds in the bottom of the basket and then the coffee on top as well.
We actually tamped as a regular shot, and put 1/2 a packet of Sugar in the Raw on top of the grinds.

What's worse:
(assume you must make a Cubano)

Channeling in a shot because the sugar is in between grinds and it dissolves?

or

Putting sugar on top of the grinds and having to backflush after the shot everytime?
Yes. It will cause damage to your machine eventually. The sugar should be poured in while the espresso shot is being made. That sounds like common sence to me. But different coffee shops have different ways of doing things. Recently I went to a locally owned coffee shop and asked for a pretty popular drink in the area and come to find out as he was "making" my drink all the espresso, milk, sugar was in the milk jug ALL MIXED TOGETHER. I was like "what the &@$!". The barista told me that everyone loves it. How could any decent coffee drinker take that into their body? It's not fresh espresso, the sugar sits at the bottom and if you wanted the drink hot that would steam it! Steam espresso, milk and sugar? Shit like that is insane. But sugar mixed with the grinds doesn't sound like such a grand idea. People should just use what things are suppose to used for not find some innovative bullshit way to make the job easier. What a waste and what damage that is going to cause to the machine.
Would you kindly, and without using profanity, explain how sugar in the filterbasket will "cause damage to your machine eventually"?

As a customer, you do have the right to request that they remake the drink differently. Doing it that way and explaining why might do more good than cursing about it in a discussion group.

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