Things which just won't work with Debian (woody)

1. Automated security updates
Normally, apt-get upgrade can be used to retrieve security updates in a non-interactive manner. This does however not work with sendmail (which asks 2 stupid questions which only require the default answers anyway) and proftp (which uses /dev/tty in its postinst file).

2. Locales
The locales generation is broken when using it the first time. Call dpkg-reconfigure locales again to fix it.

3. Drivers
The boot-floppies don't contain the gdth.o module by default, which is a pity especially if all servers require it...

4. mkfs.ext3
The standard version doesn't work on loopback devices, this is fixed now, but the tool still isn't in the default $PATH of normal users.

5. Apache + SSL
It is not made clear that if people want apache + ssl for consumption by the general public, they must install apache-ssl, but not libapache-mod-ssl. The latter doesn't work with some broken browsers.

6. MySQL
The standard maximum value of broken connections is way too low. MySQL is unusable on woody without frequent flush-hosts command invokation.