Why Reinstalling Tinyproxy on Debian Can Leave Its Config Missing

For a file registered as a dpkg conffile, deletion is a local configuration change the package manager can preserve. A normal reinstall need not restore that file, even when the package download succeeds.

First identify the installed package's recorded conffiles and the actual missing path. A maintenance-script-generated file is another case, and a path copied from an older package may no longer apply.

For a confirmed missing conffile, dpkg documents --force-confmiss during a deliberate reinstall. This requests missing-file restoration more narrowly than a purge, although it can restore other missing conffiles in the same operation.

Purging removes package configuration and can invoke additional cleanup. Choose it only as an intended reset, backing up what must survive.

After restoration, review listener, client permissions and upstream settings before allowing service exposure. The vendor sample is not your private deployment policy, and package installation may interact with service management.