 [ Symptoms ] i am unemployed and 47 years of age my cobra expires in may 2014  since my cobra expires around mid 2014 do i need to buy alternative obamacare exchange insurance by december 15 2013 effective march 2014 to ensure i will have both continuing coverage and face no penalty for 2014 how is the answer changed or impacted by 1  the potential for future employment with health benefits prior to the cobra eligibility expiration deadline 2  previous active duty u s veteran status honorably discharged but not pension eligible or 3  my state of residence ny [ Disease ] you can hold on to cobra until it expires at which point the loss of insurance will be a qualifying event that allows you to buy another policy even if it is outside the open enrollment period but you would be well served to search your state is marketplace this fall for another plan that starts january 1 2014 it is quite possible you will find a less expensive insurance policy especially if you qualify for a subsidy if you find a better plan you can drop cobra at the start of the year when your new plan kicks into place if you then get a job that offers coverage you will drop your marketplace coverage and be covered by your new employer