Am I missing something obvious? I always thought -default was checked last and I can't see why its not using the exact match on .qmail-bob-clamav
There was some discussion of enabling such support in vpopmail. If you look in your assign file, you will find that your address will become domain-bob and qmail-local will be told to look for dot files in /home/vpopmail/domains/domain. You are missing the effect of the virtual domains in qmail and vpopmail's assign entries.