I do sysadmin work almost exclusively. The scenario you're describing is, basically, the norm in my life. I'd take at look at OS and application service logs,

I do sysadmin work almost exclusively. The scenario you're describing is, basically, the norm in my life. I'd take at look at OS and application service logs, then break out the various flavors of diagnostic tools-- strace, ProcMon, etc. It's not ideal, but it's the sorry state of affairs in the industry. Insecure-by-default isn't the answer to bad error messages.