The last time Jupiter transited my asc... can't think of anything that dramatic happening...but I did return to dental issues at the time happily ended up with a very good private pratice dentist. I guess this in a way is significant since my natal Saturn is on my dsc...(bones, teeth, one-to-one/private practice/specializations..I also have Mars on asc..knives, cutting..etc). Transiting Saturn was in Cancer in my 11th..(trining my Moon/Venus). I think these in part helped to offset the natal t-sq that my asc Mars/Saturn dsc are part of..) and also the dental situation to be more positive and pleasant (than I've experienced).
Previously to the abovementioned, an earlier Jupiter crossing asc transit, was more significant. I moved from my childhood home...things were very turbulent with my parents and I because of how it all occurred. Also, transiting Jupiter, not yet at my asc, was in my 12th square my Moon/Venus. I was in the early stages of what would later become my first Saturn return, and transiting north node transited my natal south node in 6th...which is to say by the time that Jupiter did cross my asc things were pretty much already a sorespot.
Desz