ESTA/WVP - leaving US within 90 days, then staying in DR
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Accepted answer
The "neighboring countries" clause in the Visa Waiver Program is intended as a way of stopping people from doing "visa runs" to neighboring countries to re-start their Visa Waiver clock.
In your case you are clearly not visiting the DR as a "visa run", so you will not have any issues at all.
In practice, presuming you are leaving the US by air, then when you travel from the US to the DR you will be deemed to have left the US.
On your return to the US, the immigration staff will see your prior visit, and have the ability to basically "re-open" your previous stay, meaning you previous 90 day period will continue - giving you ~2 months further legal status in the US. (In practice they are just as likely to treat you as a new entrant and give you another 90 days, but either way will work for you in this case)
When you leave the US the second time you will once again be deemed to have left the US. As you have no plans to re-enter from the DR, then that is treated as your final exit date from the US on this visit.
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