app not getting called

Question

Was not sure where to post this. Anyway, I have a c# console app that accepts 3 params. It then does a file copy, calls a stored proc, then updates a log file. We are calling this app 300 times in succession(sometimes as fast as once a second). I am getting intermittant failures. By this I mean it just doesnt fire at all. Our goal is for the sql agent/job to build a pdf form data, then call this exe, which moves the file and publishes it to a portal. Any thoughts on a better way to do this or what may be happening?