Issue with SSL and Images

We have a webserver that is running windows 2000 SP4. Our server
generates letters which pulls its logo/letterhead from an images
directory via HTML tags. The images are .jpg format. Well recently we
enabled SSL because of HIPAA policies. after doing this our images were
inaccessible. We rewrote the code to look in either http or https. the
images started pulling again. When we generate a letter it displays a
copy on the screen, which will allow you to print. When you print it
some times and very sporadically the images will not print. There is
also a copy of the letter saved in the system and when we open it to
reprint, the image is there and it will print. when the letter displays
the first time the image is there as well. It's pretty hard to tell
when the image will not print because it always displays on the letter.
We disabled SSL on the images directory and on the letters directory
and it still happens. we disabled SSL on the whole site and it still
happens. We are at a loss of what can be happening here. I hope some
one has a clue about what could be causing this.

Jason Hall