Cuba Trip for rookie...

Is she a US Citizen, traveling on a US passport? Does she has a license and all the paperwork from the OFAC to be going there? All important questions.

If the answer to any of those is yes, she most likely won't be getting any cigars through customs. If she tries, at best they are confiscated and destroyed, at worst, she could be in deep sh!t.

My advice would be don't take the risk, even if it's an official trip. There are plenty of other ways to source CC's if needed.