Actually, my short-term losses usually exceed my short-term gains. Rolling covered calls (over the past two years) has generated a lot of realized short-term losses.

In reality, I always roll at net-zero or at net-gain. So, there is no actual loss. After each roll, I either have the same amount of cash or more.

However, since I am rolling to a higher strike and I am still holding the underlying long, I also have recaptured previously forfeited long-term gains. If and when I choose to sell my underlying (directly or by allowing a CC exercise), I will realize long-term gains which exceed the previously realized short-term losses from rolling.

Why do I say exceed?

1. The premium from the sell side of the last CC roll gets folded into my proceeds (now, long-term)
2. Because I rolled at net-zero or at net-gain, the final reconciliation always results in a positive number
3. Add underlying appreciation

So, yes, I have booked real (and sometimes HUGE) losses. On the flip side, I have equal or greater gains.

Now, one may quite appropriately interject that my underlying can suddenly tank. Yes, that may happen. If it does, I still get to keep that last (and greatest in amount) CC premium.