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? How do I change plans? Will Pennie replace HealthCare.Gov in Pennsylvania? How do I cancel my insurance plan I purchased through Pennie? How do I report changes for 2021 coverage after Open Enrollment ends? Can't find your answer? Find local assistance or contact us.