As part of my mechanical ESPP sale strategy, I sold my ESPP shares from the recent enrollment period today, the first day they are available for sale.
Thanks to today's upgrade from SG Cowen, MSFT enjoyed a nice run today and closed at $28.14. I sold my stocks earlier in the session at $27.89. Compared to the ESPP purchase price of $22.23, it is a nice 25.5% before-tax gain or 19.1% after-tax gain in my 25% tax bracket.
Admittedly MSFT sports a nice upward trend recently, but I continue to be bearish of the stock and the overall stock market. If MSFT continues its march, I will be happy to cash out some options down the road. Being a contrarian, I tend to play defensive in settings like this.