There are a lot of theories as to price behavior on and preceding option expiration day. Probably the most prevalent is that stocks gravitate towards round numbers as traders unwind positions because options are pegged to round numbers. Therefore, some big moves can occur especially in the last hour. Another is that stocks tend to trend the week before options expiration. So you go with whatever the trend is and then fade it at the end of option expiration day.
I, personally, don’t pay much attention to option expiration. But if you’re interested, James Altucher has a couple of options expiration systems that he uses. One of them uses the following rules…
“1. The S&P makes a 4-month (80 trading days) closing high.
2. The VIX closes within 10% of its 4-month low.
3. It is the Friday the week before option expiration week (one week before option expiration day.)
If these conditions occur, then buy on the close of that Friday. Then sell the close of option expiration day one week later.”
Obviously, the above conditions are not going to be in place very often. But when they are, it evidentially is good bet.