My truck did something extremely similar with some differences. See below:
2014 Lonestar Crew Cab 5.7L HEMI
Truck was at least 35-45k miles. So it was well broken in at the time of this occurrence. Prior to this happening, I never had any issues with start up/smoke/shudder, etc.
I was at my buddies fixing to leave for a track day and I got in the truck to start it and it had some trouble turning over. It started but it took longer to start.... almost like the motor was having trouble igniting in a sense.
If a normal start up takes about 1-2 seconds from when you turn the key, then this was taking about 3-5 seconds. Then once the motor had started it seemed like it was about to die. It had a very rough idle and was also very low. I saw all the white/blueish smoke in my mirror and my buddy also commented on how much smoke there was. (It really was a lot..... obviously not normal...).
Truck was parked on flat surface and it was not a cold start. I had a maintenance plan with MOPAR and also had it serviced at proper intervals at the dodge dealership. Temperature outside was warm (80-90s IIRC). I turned the truck off and turned it back on. Similar experience except this time not nearly as much smoke. I put the truck in gear and it seemed to drive fine. So we drove 3 hours to our track day, did our thing and left the next day. I never seemed to have any issues with it again that weekend. Then the next week it was doing the same exact thing again.... but it was intermittent. It had done it on hot starts, cold starts, level surfaces.
Well, I take the truck to the dealership and explain what happened. I leave it there with them and they get around to checking it out in a day or so. The service advisor called me and said that they never saw the smoking or starting issue. Though he said that the last oil change over filled the capacity. I then said... well every oil change on that truck has been from y'all. Ha... he kind of back tracked and said "Ooooh, yea it does look like we did the oil change".. then I'm thinking well I'm glad you didn't hydro lock the thing (I guess you would have to REALLY overfill to do that. Not sure if you even can do that with oil? or if there is some overflow valve that would not allow it to do so).
Anyways, the day I was going to go pick it up, it did the issue on start up. They called and told me they experienced it and were not sure what was going on. They told me they thought it was the fuel pump. So they were ordering a new one. I took my truck and just continued driving it. I never really experienced it again (if I did it only happened like one other time). They never seemed to order the fuel pump/ follow up with me so it just kind of went away.
So.... yea. I don't know if this helps at all but knowing that similar stuff has happened on other trucks that clearly were broken in. The service advisor described it not as a weak start but rather a long start. Frankly they were extremely puzzled and had never seen anything like that.