Let's do a small experiment: root# dpkg -i dummy_1_all.deb Selecting previously deselected package dummy. (Reading database ... 288646 files and directories currently installed.) Unpacking dummy (from dummy_1_all.deb) ... Setting up dummy (1) ... # No postinst, no preinst, nothing root# cat /var/lib/dpkg/info/dummy.conffiles /etc/dummy/test1 root# ls -l /etc/dummy/test1 -rw-r--r-- 1 root root 9 Mar 18 01:01 /etc/dummy/test1 root# cat /etc/dummy/test1 coshoopu root# echo "I am a bug" > /tmp/a root# rm /etc/dummy/test1; ln -s /tmp/a /etc/dummy/test1; cat /etc/dummy/test1 I am a bug root# ls -l /etc/dummy/test1 lrwxrwxrwx 1 root root 6 Mar 19 22:19 /etc/dummy/test1 -> /tmp/a root# dpkg -i dummy_3_all.deb # new conffile (Reading database ... 288653 files and directories currently installed.) Preparing to replace dummy 1 (using dummy_3_all.deb) ... Unpacking replacement dummy ... Setting up dummy (3) ... root# ls -l /etc/dummy/ total 4 lrwxrwxrwx 1 root root 6 Mar 19 22:19 test1 -> /tmp/a -rw-r--r-- 1 root root 9 Mar 18 01:15 test1.dpkg-new ########################################################## #===================> No prompt ! #Nothing said about anything changed. ##########################################################