Unfortunately we cannot debug docker installs as that is a community contributed installation guide. Perhaps someone else here can help you out (e.g. @Ben-Lubar ?)
@BDHarrington7 Correct. At current, we do not associate uploaded files with a particular user, although there should be plugin hooks in place that will allow third-party plugins to maintain this association (for expiry purposes, etc).
Please submit a bug.
P.S. dev means development version