Yes, you can "float" for 60 days without signing up for and paying for COBRA and wait until you are in need of healthcare. After the need you can sign up but you will have to "back"pay the coverage too. So waiting to the last day will mean you owe the two previous months of premiums.

Problem with that plan is (was, as we discovered) you can't get medications filled at the discount price, and you can't get 90 day scripts filled at all in case you need to hide from the world. Given the spread of the pandemic we decided to take the hit and get the coverage ahead of potentially needing it.

Its sounds like that's what they were holding out to do, but their 60 day window was closing so even though they didn't need healthcare they figured with what's happening they needed to execute the option and keep their insurance before losing it.

Be careful with that, you have a grace period to start paying for COBRA but it's only a couple of months. (the exact date will be on the letter you get from your employer when you're terminated)

If you go entirely without coverage you'll likely still have to pay a fine on your taxes, though it's probably less than COBRA.

I'm pretty certain this fine has been removed from the Affordable Care Act:

https://web.blockadvisors.com/tax-reform-removes-the-afforda...