I'm visiting the States on ESTA, after which I' flying on to Mexico, then to Cuba, then to Jamaica and then back to the States, then back home (Europe). From the first US entry to the final day in the US, not more than 90 days pass.

My ESTA expires five days after initial entry. From the CBP website: "If your ESTA expired after you arrived into the U.S., it will not affect your departure. However, once you have departed you will need to renew your ESTA in order to re-enter the U.S."

Mexico, Cuba and Jamaica are all listed as 'adjacent countries' that do not interrupt the 90-day-period when returning to the States, but I'm unsure about daisychaining more than one of them.

Does my flight from Jamaica to the US count as an re-entry by ESTA definitions?

I'm visiting the States on ESTA, after which I'm flying on to Mexico, then to Cuba, then to Jamaica and then back to the States, then back home (Europe). From the first US entry to the final day in the US, not more than 90 days pass.

My ESTA expires five days after initial entry. From the CBP website: "If your ESTA expired after you arrived into the U.S., it will not affect your departure. However, once you have departed you will need to renew your ESTA in order to re-enter the U.S."

Mexico, Cuba and Jamaica are all listed as 'adjacent countries' that do not interrupt the 90-day-period when returning to the States, but I'm unsure about daisychaining more than one of them.

Does my flight from Jamaica to the US count as a re-entry by ESTA definitions?