When I run docpad run, there are times after I write changes to disk, and the process tries to regenerate it fails to do so. It's not a matter of it taking a long time, it just fails to regenerate, even on subsequent writes. I have to interrupt the process (i.e. ctrl+d in the console) and restart the process all over again.
My env:
Has anyone encountered this behavior before?
As a precaution try running ulimit -n 4096 in your console.
This has solved a number of miscellaneous failures in my docpad instance.