An interesting dilemma has cropped up recently with Microsoft's latest patches. Actually this is something that has been going on for a long time and from a consultant point of view, who is merely trying to keep the computer working and hopefully working well, will find very interesting.
Personally since I deal with a number of clients with varying software installed, I have usually kept the systems in full 'automatic' mode whereas all the critical updates are done as they arrive to the computer. But as of late, my strategies are changing due to this exact issue that has happened with the latest set of windows updates, as discussed by this ZDnet Blog.
For this reason alone, you should realize that communication is truly the key and with the right communication many issues can be prevented. Therefore the next time you see something pop up on your screen that you aren't sure about, or simply aren't sure about anything to do with your computer issues, don't wait until it is too late! Your computer tech would probably appreciate knowing ahead of time that you have noticed little issues.