I do OTM CC's on pumps with stocks like ROKU. You need to pick the right stocks, MSFT isn't one of them. The other thing is to be patient. If it's stagnant or taking a shit, you may want to wait for the pump. I generally do 1-2 week, depending on what it looks like, sometimes I'll do longer, then buy back on a shit, rinse, repeat. Timing everything perfectly is impossible, but if you play a handful of them, it's easy/free money. Basically you need to get in on movers early, hold, and when they get nutty, you can do OTM CC's on them for free money, while (ideally, depending), not getting assigned.
Example, if I have 1,000 shares of TSLA that I paid $450 a share for (current being $750) and the week looks like shit, I do a OTM CC at $800 @ 500ish per 100, free $500 per 100 if it doesn't hit $800.