My single expiring option for May finished in the money, so I decided to roll it out to July before taking the assignment.
While IWM was trading at $136.43, I bought to close one IWM May $138 naked put and sold one IWM July $138 naked put and received $283.60 after paying $2.20 in commission for the two legs of the calendar spread. IWM ended up closing at $136.00 on the day and which meant I did a little better than I would’ve if I had waited until the very last second of the trading day.
I posted my video of the trade here: