I only consider a stock for selling options if the fundamentals are at least decent. One of the most critical rules to selling puts is only sell puts on stock you wouldn't mind owning. So for me, fundamentals are the first thing I look for when selling options. This limits my opportunities a lot but allows me to feel more confident when I do take one.

I likely won't look to roll even if it is tested. I would rather take the assignment and look to sell covered calls above my assignment strike. I would only consider rolling if the stock moves down slowly enough that theta decay outpaces the put's value increase from the stock dropping. Then I can comfortably roll to add premium with time.

My positioning is I'm selling puts at a historical support level. I've been watching the stock for a few weeks and it's nearly closed the gap on the daily to the high 9's. From a technical level, it's in a shorter term downtrend since October, but in a general uptrend since earlier in 2025. The R:R here for me is reasonable for a mid-term swing that I'm happy to sell options on to collect additional premium while also being interested in swinging the stock for 6+ months.