Several others with ideas.@adiggs or others: just found this thread and now going through all 790+ pages1 Wondering if advice for being stuck in a covered call that's deep ITM. $900 with a May expiry. My plan was to roll each & every week, but getting harder to roll flat. My other thought was to just bite the bullet and roll to a 2024 leap at a price where I'd be comfortable to exit the stock (which of course would be v. painful!)
One question that you didn't indicate - do you have any sort of a schedule for the position? I.e. is there a point in time where the call will resolve, either by assignment or by you paying up and closing it out? I have some shares / calls, for instance, that I'll close early in April to pay some taxes. Hopefully some more soon for a down payment on a house. The point here is that with a schedule, that limits the available choices.
I don't know I have a lot more to add to the observations others have. I've done the far roll to get far OTM. That worked and I figured selling shares at 840 would be fine by me - shares were around 300 at the time. And then we've shot up and suddenly that 840 strike cc wasn't so fine anymore. That's the big problem with a really far roll.
If you do start looking at a long DTE roll for big strike improvement, be sure and include 6 month and 1 year options in your planning. I've done both 1 year and 2 year options, and I found the 1 year to be seriously better. Just because it wasn't so far out, and the resources weren't locked up for so long.