While this has been an ongoing issue for me for the past several months, such that Quicken automatically skips (especially past-due) bill iterations, I love that this happened just in time for me to realize that I am short nearly $1K at Christmastime because I was relying on this software that I pay for to help me organize my finances and basically be a responsible human being.
Quicken has become more of an online-based accounting game for me, where I try to figure out where it has glitched and I work to correct it, only for it to glitch somewhere again the next time I work in it. At this point, I would say it is TREACHEROUS to rely on Quicken to accurately help budget and forecast, no matter how meticulously one enters data into it.
Those of us who care enough to use personal financial software are really trying to self-manage our finances and our LIVES and we rely on this software to help us by being an accurate steward of our data and to function as it purports to. Please take these issues as seriously as we do.