Your truck will normally perform a regen as needed and you will not know it unless you happen to smell the excess fuel or if you have installed a digital monitor (like an Edge CTS) that informs you of a regen.
If your truck requires a regen, and your driving frequency/habits don't give your truck enough ample opportunity to perform a full regen, the DPF will start to clog until it reaches a preset point at which it will then give you the warning that a regen has begun and that you should continue to drive so it can finish the regen.
For someone that works their truck pretty hard, or does very few short trips, their truck will perform regens and they'll likely never know about it. For example, my commute to work is about 20 minutes of highway driving, in 60k miles, I have never had the regen indication on the dash, however I know that it regens somewhat frequently. Sometimes I can tell, usually I can't.