Just so we are clear you would be talking about an unattended dist-upgrade from lenny to squeeze? Have you done this?
Please explain how your automated Debian administration system that has been in place since Lenny[^1] handles unattended dist-upgrades without the use of preseeding the debconf database for questions with a priority of high or critical?
[^1]: Squeeze was February 2011, any new stable installation since squeeze defaulted to dash as /bin/sh
EDIT: Nevermind, I answered my own question, unattended dist-upgrades from Lenny to squeeze is not something you have any experience with: "I'm now using Debian Wheezy, after primarily using Windows environments my entire life." https://news.ycombinator.com/item?id=6564610#up_6565766
Please explain how your automated Debian administration system that has been in place since Lenny[^1] handles unattended dist-upgrades without the use of preseeding the debconf database for questions with a priority of high or critical?
[^1]: Squeeze was February 2011, any new stable installation since squeeze defaulted to dash as /bin/sh
EDIT: Nevermind, I answered my own question, unattended dist-upgrades from Lenny to squeeze is not something you have any experience with: "I'm now using Debian Wheezy, after primarily using Windows environments my entire life." https://news.ycombinator.com/item?id=6564610#up_6565766