It could be you have your hair twisted too tight.  This makes it harder for the sticks to slide through the hair when securing it.  Try leaving the hair a bit more loose when creating the bun and see if that helps.

Hi Shannon,
I just PM'd but I am going to post some of it here because it might help someone else, too.

I would first look at my hairsticks.  Are they smooth?  Are they thick? 
I like narrow sticks the best like Longlocks and Quattro Steelstix.
Are you twisting your hair up like in a French twist?  One foolproof method I use is to ponytail with a scuncii soft and gentle ponytail holder, wrap the (usually damp) hair in a bun, pin with a couple of hair pins, place an invisible hairnet over the bun and wrap the excess around and underneath the bun, pin around edges again, then insert the sticks very gently almost behind the bun.  This will stay up indefinately for me and I have fine, slick hair.

If you are doing a twist, I would comb it all back to the nape, twist and keep twisting until you get almost to the end of your hair, then tuck under the ends at the top.  At this point you can either secure it with pins as above but without the net (this sometimes helps with shorter hair) and position the hairsticks as decorative instead of actually holding your hair up alone.  Or you can start at the top of the folded under hair inserting the hairstick and using a sewing motion to pick up twisted hair and secure it to scalp hair. 

This is pretty simple really, but are you making sure your hair is well detangled before you put it up? 

Could any of your hair products be leaving the hair tangly thus preventing the hairsticks from sliding through easily?

Let us know how you get on; there are lots of people here with tons of experience with hairsticks.  I'm sure together we can help you troubleshoot this thing!

HTH, 

You might also look at the following things; I know that sometimes the solution to a problem is right there if I just question everything.

What is your cleansing routine? Many people do well with CO (conditioner only) washing, some use CWC (condition, wash, condition) and some use shampoo and conditioner.

Do you dry oil your hair?  This might make it a little easier to slide the sticks through.

Do you use a shampoo with a lot of detergents like sodium lauryl sulfates, etc.?
Rinsing very thoroughly if you do use shampoo is very important for the condition of your hair.

If you use products with protein added you might want to use these more sparingly and not as often.  Some people have no problem with them, I like to use them only occasionally.

A hair conditioner with a 'cone in it might be helpful.  Many of us don't use products with cones, many do.  But they will give your hair more slip.  if you do opt for a sillicone containing product, you might want to clarify with a vinegar/water rinse from time to time.

HTH,

Hey and thanks for the replies!
First of all, I think that I was wrapping my hair a little too tightly because it is kind of short. I am detangling it properly, I use a wide toothed comb to detangle very gently. I use Selsun Blue Shampoo, because I have sebhorreic dermatitis, and I can't get away with using anything else or going CO.  My hairsicks are tapered, and in a kind of square shape, so that they taper in a sort of narrow pyramid shape. They are smooth. I don't use dry oil, and didn't plan to, because I have oily hair to begin with, so the day after I wash it its already starting to look dirty. I am being more careful with the hairsticks now, and I'm not using them in wet hair, just in case. My hair is just past shoulder length, so it's not so easy to get up into haisticks yet.  Once it's longer, it should be easier. Thanks for the great advice!
Shannon