Welcome jimjenkins!
Some things to assess;
Have you been closing the clasp properly?
How old is the strap, is the pin portion of the buckle fully going through the strap?
Do you wear your watch very tightly? If you do, you will cause the pin from the deployant to stretch the leather and thus increase the punched holes in the leather strap.
What kind of strap are you using? Is the hole the right size? The strap is supposed to be padded, but not padded on the portion where the holes are.
Let's see some photographs when you get a chance!