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Planning on leaving your job next year? Switch to the lowest-cost plan during this year's open enrollment. Then, after you quit, federal rules (known as COBRA) will let you stay on your employer's health plan for up to 18 months, although you'll usually have to pay the full cost, plus 2%. Once you've tapped out COBRA, you must sign up for a new policy within 63 days or insurers can legally turn you down or refuse to cover pre-existing conditions.