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After you file
Your employer would have paid Cobra insurance premiums under the subsidy program so they will be the place with the answer. If you are unable to get the answer from HR in a timely manner you may need to extend.
First you need to be sure you understand what the question is about. The Cobra Assistance Subsidies have already been excluded from your Federal Adjusted Gross Income. MA does not conform to the Federal Exclusion of these subsidies. Answering "Yes" to this question and putting an amount in the box will increase your MA taxable income. If you click on the Learn More link on the page you will see an explanation that states:
Therefore, such COBRA continuation coverage subsidies provided to certain individuals must be included in Massachusetts gross income.
Below are two links explaining the Cobra assistance program and how you would have applied. You would have filed a specific application with the MA Insurance Commission through your employer to request the subsidies. The first link has an example of the appication. You had to apply prior to 31 Jul and the subsidies would have ended by 30 Sep.
Summary of Cobra Assistance program
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