What is Open Enrollment? August 24, 2020 17:55 Updated The time period each year when Pennsylvanians can shop for and purchase health insurance through Pennie. This year, the Open Enrollment Period is November 1, 2020 to January 15, 2021. Related articles What is Pennie? Will Pennie replace HealthCare.Gov in Pennsylvania? How do I change plans? Contact Us How do I cancel my insurance plan I purchased through Pennie? Can't find your answer? Find local assistance or contact us.