I have searched this issue in the forum but didn't get the information I needed. The other day the my headlight didn't come on at night like they always did, so I manually turned on the switch and they popped up. I investigated the issue further the next morning, the automatic light feature does work, all other light(interior, side panel and rear) do come on when I release the E-Break but the headlight don't turn on or pop up but they did turn on and pop up if I turned them on manually. This worked for 3-4 days.

NOW all the symptoms remain as is expect that the passenger headlight turns on but does not pop up when i manually turn the lights on. It does not make any griding noise. I can pull the light up without and restrictions. I drove the car around, each time I hit some sort of bump the light falls down a little bit, with a few more bumps its was back in all the way. Would this be the plastic gear inside or the motor actuator pin? if it's the actuator pin how what is the fix? and not sure what's going with the automatic light feature

Well start with the headlights are junk. You need to examine the assembly the actuator arm sounds like a good place to look. It connects the lamp to the motor. There is a pin that often works its way loose and then out. If it is gone look inside the front area for it.
As for the operation issue check the grounds for the headlight motor insufficient current could be your cause. best of luck

If you can raise the headlight from outside in front of the car with your fingers it is the pin. Ask me how I know. Once that pin is out the headlight wont raise by the motor. It is held in place by one of those press on washers that bites. Good luck finding one of them. None of the small parts for the assembly are available individually. Auto parts store or hardware is your best shot. If that is what it is. Best of Luck

I can raise the headlight from outside with my fingers. Couple of other things hopefully they will help diagnose this problem

1. when I turn the lights on the headlight motors turn and run longer then the motor on the other side.
2. If i turn the headlights on and raise the headlight with my fingers, then turn the lights off the headlight does retract back in, although it doesn't go in all the way, if it traveled another inch or so it will be in all the way. I can push it down into it's place.

I checked the elbow joint under the headlight which pushes the light up or down, seems like it's in place.

Check for blown fuses in the panel under your passenger's side floor board. I think it will be fuse #6 and #20 but I am not 100% sure. I can't remember S*%t now days...in fact my memory is my second shortest thing.

Did you check if the Nut that holds the Motor is torqued to the right specs ? From time to time it may get loose and not raise or lower the Headlight properly....... also double check the washers (plastic stoppers located on the arm that raises the headlight) they do get damaged from the pressure and cause the arm to travel farther than it should...... by what you explained that is the most likely trouble that you have.

I'm not sure which pin leadfoot is talking about, other than the link arms that you said looked fine.

Most limp headlight issues are due to stripped plastic gears inside the operator gizmo. Click here for the best brass gear replacement kit that I know of. Make sure you get the right version for your year car. This thread has more info about the gears in posts 2 & 27. If you get Rodney's kit I linked to, it includes a metal bracket that goes over the plastic piece you have to glue back together, so the glue isn't the only thing holding it in place.

Normally if the gears are stripped you'll hear a grinding noise. Try raising the light by turning the manual operation knob. If you have a cordless drill and bit adapters, use that instead of your fingers. If you hear any grinding/popping, it's the gears. If it doesn't move at all, try raising it by hand while still turning the knob, I'm guessing you'll hear the grinding when the light is about half way up.

If it were my car, before ordering anything I'd pull out the headlight motor (just the motor & gear, not the entire headlight assembly), then take the plastic cover off to get a look at the gear.

Once you have the metal gears the problem will be solved (one brass kit = 1 side of car), but I firmly believe that the 'twighlight' feature of the C5 is what causes most of these problems in the first place. Sitting still it's fine, but just a few times of your lights turning on at interstate speeds and those plastic gears are toast.

So, it turned out it was the gear, but the actual teeth on the gear are fine, problem was the fin that the motor needs to turn the gear were broken off, needless to say I order a set of brass gears and replacing them this weekend. Thank you for help guys. After this i'm tackling the auto light feature, it does everything as it's suppose to but the headlight don't pop up, all other lights turn on and off just as they should.