Checking out files already checked out

[SpartanHokie]

Good day,

I have a Visual Build Pro file (run from a web environment by calling VisBuildCmd.exe) that does quite a few things, one of which is versioning our software. To do this, we check out all the AssemblyInfo.cs files, update the build and then check the files back in. In order to prevent our developers from checking these files out, we keep them checked out to the build user. The problem is that when it goes to check out the files in step one of the process, it fails. I have the flag to say Yes to everything unchecked (basically saying No to everything). No if after it fails, I go and run it again, it succeeds. more weird. If I keep doing this, exactly half of the builds are successful, the other half fail. Any ideas????????? Thanks