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Answer to question 1: you COULD do this, and it is the safer approach, however you are then losing some (not a lot but some) potential profit. When I backtested MSFT, there was only one instance where whiplash forced you out of both positions. Over a 6-8 week period, losing that .10-.15 for closing the other long out early just eats up too much profit, for not much risk reduction. This is a great question though, and a good example of risk tolerances. Each trader has to set their own, and make decisions they are comfortable with. I would never say closing the other short, to capture the gains there, is the wrong decision -- its just not what I do. If I get whipsawed 2-3 times, I'm certain I'll change my mind. Answer to Question 2: I'm not sure I 100% get what you're asking. If I close one short because the strike gets hit, I do NOT roll to another strike -- I get out. Rolling is a recipe for disaster as you're betting against the trend -- you get less premium as there's less time in the trade, so if your second strike gets hit, instead of BE or a tiny loss, you have a big loss -- roll again and repeat. I tested thoroughly whether I should roll or close, and the answer, every time, was close. When rolling, I typically use the double diagonal trade feature on TOS. It allows me to close out the two front shorts (buy back) and sell the next two weeklies in one trade (so one commission on four legs). However, you can't do that when you've closed out one leg because the strike was hit. In those cases I use the calendar trade feature to (in this example) buy back one put and sell next weeks put, then just sell the next week call (so two trades -- two commissions). I have yet to find a feature that lets me put in three (even customizing some of the options they give). If you have one, let me know, I'm all about reducing commissions.