If I sell a put for 5.00 at a $20.00 strike and the underlying is at 15.00... overtime it gets to 20.00 and eventually getting to $25.00 (my pain threshold -5.00) Now I know that an option buyer can exercise whenever they want but that it makes less sense when there's still time left on the option. So if I want to doubleout like this on an option which would seemingly bring it in the money what is the risk of being assigned? Should I be sure to buy it back a week or two beforehand when it's lacking in much time value so I can simply buy back as much intrinsic value as I can and keep the time value? Is the risk of being assigned early more prevalent on a more volatile underlying? Or about the same since a higher vega is already built in.