I like to time my covered call contracts to contain the dividend dates. You maintain complete ownership of the stock and the rights that come with that ownership while you have the open contract. The contract only obligates you to sell the stock at expiration if you still have the contract open; you can buy back the contract at any time before expiration. You can see I did this in the red below. I locked in the gains and resigned a new contract. The stock did not gain or lose between 7/01/2016 – 12/31/2016, and that is some of what we can expect with these huge companies, so sign up for your ESPP, and count the discount as “average profit”, then beat that “on average” with options.
Sorry I don’t have good records before these dates.
When the call was assigned to me, I had to sell my 100 shares. So I bought another 100 shares with that money through my company’s ESPP. I make a very simple phone call and leave a voicemail on their answering machine telling them how many shares I want to buy. I have to leave this voicemail before 12 AM. If that isn’t enough time to decide if you’re getting a good price… Then I don’t know… Just keep reading.