Rolling covered call on long term portfolio

[The_Krakenite]

After re-reading the original post, I suppose there could be the case where if he waits a bit longer before giving up the stock, he'll only have to pay longer-term cap. gains tax, instead of short-term. In that case, I won't complain if you want to roll in that spot.

 

[john7722]

I think I understand it a bit more now. So the goal is to outperform the underlying but also to keep the shares for longer then 1y for tax purposes. The biggest problem is when the stock goes up too much over the strike price and you are Deep in the money at exp. . So now you have to bay back your call at a huge loss.
The only way to recover this loss is to sell another call at a higher strike price but this time you would have to sell maybe 3-6 month out instead of 1 month out.

If the stock keeps going up and you end up again deep in the money you would have to roll your call maybe 1-2y out. And if the stock keeps going up and up you will eventually not be able to roll out to break even on the call and you will be forced to sell your shares and underperform compered to the stock.

Is that correct?

 

[The_Krakenite]

So , this sounds like you should always sell calls on your long term holdings. Doesn't it?

I think you may want to look up how volatility works, etc. These kind of banket-statements 'always do this/that' will lead you to all sorts of tiny-reward, bigger head-ache type risks.

It almost sounds too good to be true.

There is a saying about that... if it sounds too goo to be--

It's a zero-sum game. Actually, even worse because of commissions, slippage, etc.

Is there a situation when this strategy of indefinite rolling stops working and you end up losing money on your calls?

Sure, you could roll until your account blows up. When you roll, you are TAKING THE LOSS. Because you are closing your contract outs and locking in a LOSS, then re-opening another contract on the HOPE of somehow making up for those losses.

There are limits to how much you can keep pushing your losses down the road if your trades don't start winning. Even so-called professionals have blown up accounts that way. Karen-the-Super-Trader was one example. Even worse in her case, she got into legal trouble for not properly reporting those losses, yet billing the clients for the trades IIRC.