Any help RE: 5y.son sudden crying about preschool?

I am at a loss.  my 5 1/2 year old son recently starting crying when taking him to Preschool.  We have gone over everthing imaginable, talked to the teacher, principle, dealt with topics that we thought might be bothering him and it has only gotten a little better.  Bottom line, he is a very social 5 year old who "liked" going to school, but now doesn't want to go.  We are very close and he says that he misses me so much when I'm gone that he doesn't want me to leave and crys and holds onto me.  He is the type of kid who "thinks about everything in great depth" so after pursuing several possibilities the only thing I can figure out is possibly a little bit of anxiety issues (like his father).  Is this crazy?  And does anyone have any suggestions on how to handle this?  Now a few weeks after this started we are talking about going to Kindergarden Day before fall and he says that he isn't happy about it and would rather stay at home.  We have gone to the length of explaining that sometimes we don't always like to go to school/work but these are things we have to do in life and they produce good things/experiences, etc. etc.  Any help or ideas or what or why this is happening to an otherwise very well rounded child?

[jdtm]

If you google the term "easing school jitters" you will be able to find information that should be of assistance.  There is an excellent book with this title for children who suffer from severe anxiety (selective mutism which is an severe anxiety disorder) but I see that it is out-of-print.  Nonetheless, this phrase or similar ones should give you some wise advice which should be of help.  Also, I suspect what you are seeing are signs of anxiety (it is an inherited trait) so googling terms as "childhood anxiety" or words similar should also give some assistance.  Hope this helps ...

[Sandyo71]

Thank you so much!  I will definetly look that up.  Thanks!

[musicmama]

I agree with jdtm.  I was also thinking that changing the schedule so that he doesn't have time to have anxiety might be helpful.  Can someone else take him to school?  Are there fun things he could do after school that he wouldn't get to do if he stayed home?  Is he an only child?  Of course he needs to know that skipping kindergarten is not an option.  It might be helpful to remind him that only "big boys" get to go to school.

Good luck and God Bless.

[Sandyo71]

Thank you!  There isn't another option for taking him to school and I have to work so he knows that I'm not at home when he's not either.  Yes, he is an only child.  I will add the "big boy" idea and maybe shorten his morning schedule to try to lesson it.  Thank you very much for the ideas!