The problem with DTE, is it has very little effect when there is a very deep ITM move like this. Any time you drop a few standard-deviations, time value goes to 0, even if you still have months left before expiry.
Think about it. Even if you have what are lots of (days) TIME left, when the VALUE of that time is nothing, your days means nothing. Time x 0 = 0.
How did I learn this so well? I got busted up in the historic NetFlix fiasco, and learned this first-hand... the hard way. I got hit by early assignments when the standard books will say you have nothing to fear. Only an idiot would assign weeks in advance. WRONG!
There is a certain point, where once you drop that far, rolling to add a years' of extra days into the contract will barely change the price of the option, as it is STILL expected to expire deep ITM.
Those who are new to options and think they can magically use the 'Wheel' as some sort of magical self-perpetual money-making machine will find out the hard-way why it is doomed to fail. It may seem to work for a while, which is why so many 'Youtube' gurus will swear by it to their followers.
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Edit! So I thought the OP was referring at first to shorting PUTs. In any case, my same argument applies when you think of it.
You want to sell but probably can't even get the intrinsic value, right?
The OCC still has your back. Don't worry about it.