I will be retiring in Febrary 2016. Do I have to pick a plan now before December deadline?

You need to specify your needs.

I think this depends upon your age more than anything. Are you turning 65 in February? If so, you should be applying for Medicare now and looking at options. You can apply during the three months before the month in which you turn 65. If you are already past 65 and you have continued to have coverage through your job, contact your local social security office so that you can provide the proper documentation of your employer coverage so that you don't have any penalties for late enrollment in Medicare Part B. I don't think the December 1 deadline applies because retiring is considered to be a "life event" which lets you make changes outside of the open enrollment period. My husband turns 65 in May 2016 and I have been told that he can change his regular coverage to a supplemental plan at that time.

Are you asking about medicare supplement plans or Affordable care ins?

Rusty, check with your Human Resource department to see if retirees are offered an insurance plan.