TurboTax is trying to determine if you took advantage of the "last-month" rule in 2016. That is, if you were under HDHP coverage (High Deductible Health Plan) on December 1, 2016, then you would be allowed to use the full annual HSA contribution limit, even if you had not been in HDHP coverage the full year (the limit would normally be prorated monthly).
The catch is that when you use the last-month rule, you have stay in the HDHP the entire next year ("the testing period" - all of 2017) or else you have a "failure to maintain HDHP coverage", with penalties.
Here are the workarounds:
1. IF YOU WERE UNDER HDHP COVERAGE FOR ALL OF 2016, then you can answer "none" to the question "Did you have HDHP coverage on December 1, 2016?" because the last-month rule doesn't apply to you. This will skip the break message.
2. IF YOU WERE NOT UNDER HDHP COVERAGE AT ALL IN 2016, then you can answer "none" to the question "Did you have HDHP coverage on December 1, 2016?" because the last-month rule doesn't apply to you. This will skip the break message
3. IF YOU WERE UNDER HDHP COVERAGE FOR ALL OF 2017, then you can answer
"none" to the question "Did you have HDHP coverage on December 1, 2016?"
because you satisfied that "testing period" whether or not you used the last-month rule. This will skip the break message.
4. Only if you started HDHP coverage sometime during 2016 and stopped sometime during 2017 do you need to answer Family or Self - because this is the situation that this part of the interview calls for.
