As long as the SP reverses, you can roll and eventually catch up. The problem occurs when your strikes are so far OTM that the options follow the stock, with no premium value for time. For example, if badly timed, one could have sold an ATM Jan 7th 1200p on 1/3 for around $30, which subsequently became ITM by $174 on that Friday. Oops, that’s a pretty big problem, so requiring a roll to 1/14. But that put is still now $95, better because of the SP rise, but still not expiring worthless. Ok, so roll again to 1165p on 1/28 for little debit/credit. See the problem, still ITM, and rolling out 2-3 weeks didn’t solve the problem, and the SP must still return to “near” the original sale price (ok 1165 is “near” 1200) to close out the trade for a profit. If the SP doesn’t reverse enough, the trade becomes an albatross, which ties up capital for weeks or months without producing premiums. As long as the SP goes up, eventually rolled puts expire worthless. Unfortunately, that’s not necessarily the case with covered calls. If the SP rises faster than $10-20/wk (this is TSLA after all), the CCs fall farther and farther behind. I lost shares via CC during the Hertz price rise (didn’t have enough cash to buyback-roll in my IRAs) and I’m now selling puts trying to get them back at a comparable cost basis. It takes quite a long time to get back a $300 loss at $10-$30/wk.