This is NOT my go to approach to when managing ITM short puts, but is a strategy I intermittently deploy in particular market conditions. I currently have (2) tranches of short puts out in IWM and both have been rolled. I'm deploying the Covered Strangle and these are the first legs. I'm going to discuss one of them, the other I simply rolled out and down - more standard adjustment.
Overall, I remain generally bearish in IWM and the markets over the next 12-24 months. I maintain longer-term bullish bias as of now. I've been lightly invested all year, not exceeding 20% and the past 3 weeks have hovered around 16-18% utilization. I mention this for general background on the trades because it influences my decision cycle.
You'll notice on Trade 5, I adjusted my basis from 200 down to 191 by adding a little size, moving from 6 lots to 8. With the light rally we saw today, I chose to take advantage by rolling the options again - from 191 UP to 193 and from 15Jul IN to 27Jun.
By adding 2 points to my basis, I was able to roll in from 50DTE to 34, taking roughly two weeks off the trade. This does (2) things, it brings the trade closer to the more rapid decay portion of the theta curve; and it increases my delta slightly. With the small relief bounce we're seeing, I want the position to remain sensitive to shorter term moves in my direction so that I can continue adjusting the position. If the relief "rally" we're seeing fails (as I expect it to), I will be able to roll again all the same.
Plenty of ways to go about managing these, but this is a less common style of roll that has worked well for me in the past.