Weldwood Contact Cement or 3M Type 77 for attaching vinyl to pillars?

heat in general will reactivate the glue.

Your comment confirms what I was wondering, if heat reactivates the glue and say in the summer, the car is getting to 100F+ in the heat, coupled with the vinyl being stretched in order to not be wrinkled, is the heat re-activating the glue enough that the vinyl is pulling away. The reason the drivers side is not doing it, is because it has the wrinkles and was likely not stretched as much as the passenger side.

Did you prime the piece before wrapping it? IIRC, trying to stick vinyl to un-primed sanded filler is like trying to tape a piece of paper to a pile of dust.

Interesting, I did not do anything specific, ran a piece of sandpaper over the whole thing and then wrapped it. But, that makes it all the more strange that it is just the one piece refusing to stick, maybe that got contaminated with something.

Can't do anything with it for a while anyway, not only is it insanely humid, but the car is broken down at my in-laws... blew the high pressure power steering line yesterday in town and apparently the part is on back order.

Edit: so the heat + glue + vinyl is not working, car has been parked outside at my in laws waiting on parts. Called in there today and the vinyl is peeling off both pillars. Had a demo in Jason's S4 today and was looking at the flock on his pillars so leaning that way. But I might also look at SEM texture and match then to the sails. Either way the vinyl is basically coming off whether I like it or not at this point.