I was going to post a new thread about this very thing, but did a search and see it's represented here. I am also having continued problems with the cruise control. It's like what you all say - hitting the buttom at times turns it on first try, but other times it can take anywhere from several to not at all (I've actually counted button pushes to 100+).
Today was the day, took it to the dealer to talk about it and have an appointment for next week along with an oil change that's close to schedule. The Service writer said it's something he hears all the time, so another well known issue that FCA knows but isn't addressing (hemi tick, rear manifold bolts, RCSB driveshafts, etc...). I'll post results when it gets done.
With mine, there is no rhyme or reason. Weather, time of day, or anything else, can't find any common factors. Sometimes it works, sometimes it doesn't. My "cancel" button also is a sometimes thing, but hitting the brake always kicks it off. When I can get the cruise to come on, it works perfectly from then on (except for the iffy cancel).
Of course, today, when leaving the house for the dealer, CC turned on first time!
