How to Manipulate the System
If you have chronic health problems or require regular medications, and you have the money, you may want to just go ahead and elect your COBRA coverage. However, if you’re fairly healthy and you don’t think you’ll actually need coverage, you can put off making your decision for a while.
As I said above, you have 60 days to respond to your COBRA notification letter. You can wait until the last day, and mail you election form on that date (make sure it’s mailed early enough in the day to have that day postmarked). You then have 45 days to make your payments up to that point and coverage is retroactive to the end of your previous coverage.
If, in that time period, you don’t have any events that need coverage, then you can just let it go if you don’t want to pay for the coverage (or can’t afford to). If the company doesn’t receive your COBRA payment, then they’ll just not enroll you in coverage. However, if you have an event in the 105 day window (60 days notification and 45 for payment), then you can still be covered. So, if you have a car accident on day 100 and end up in the hospital for a day or two, just make sure you pay your premiums by day 105. You just tell the hospital that you have COBRA coverage pending, and they will usually hold charges pending your insurance information. This way you don’t have to actually pay for coverage of those 3.5 months unless it turns out you actually need it.