There is not enough information for an accurate answer. Even though jail is possible, it is not definite. The attorney of record would be in a better position to discuss possible outcomes.
This answer is only for informational purposes and is not meant as legal advice.
If the case in CT is not sealed it likely will show up on his criminal history. If the conviction in CT is substantially the same as the NY misdemeanor conviction he can be charged with a felony. I can't guess whether the DA will seek jail or not but I suggest that your boyfriend retain a good criminal defense lawyer.
The above answer, and any follow up comments or emails is for informational purposes only and not meant as legal advice.
There is not enough information to answer accurately. Was he convict in Connecticut? What w the conviction for? Your best bet is to hire a good attorney. Lots can be done.
I suggest your boyfriend assert his right to remain silent and to counsel to represent him in criminal court and at the refusal hearing.
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His prior conviction can serve to raise this charge to a felony. There are interstate searches. The Broome County District Attorneys Office is very tough on DWI and they are excellent prosecutors. Have him hire an attorney who is experienced defending DWI cases.
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