Insurance Ending, Do I need to Sign Up for ObamaCare? Twitter Facebook My insurance coverage ends in August 2015. Do I need to sign up for Obama Care? Answer If your insurance is ending inside Open Enrollment, simply sign up. If it ends outside of open enrollment it will trigger a Special Enrollment Period. Make sure to plan your enrollment out so you don't experience a gap in coverage. Rate and Comment on the Answer Cancel replyYour email address will not be published. Required fields are marked *Comment Name * Email * Save my name, email, and website in this browser for the next time I comment. Rate this Answer (1-5)* 1 2 3 4 5 This site uses Akismet to reduce spam. Learn how your comment data is processed.