Testing on what I proposed to Debian seems to work fine:

root@c:~# dpkg --status postfix | grep makedefs.out; ls -laF 
/etc/postfix/makedefs.out /usr/share/postfix/makedefs.out
 /etc/postfix/makedefs.out 109692331793570f2d0884efe222949b
ls: cannot access '/usr/share/postfix/makedefs.out': No such file or directory
-rw-r--r-- 1 root root 4480 May  9 12:51 /etc/postfix/makedefs.out
root@c:~# apt install postfix
Reading package lists... Done
Building dependency tree       
Reading state information... Done
Suggested packages:
  procmail postfix-mysql postfix-pgsql postfix-ldap postfix-pcre postfix-lmdb 
postfix-sqlite sasl2-bin dovecot-common resolvconf postfix-cdb mail-reader 
postfix-doc
The following packages will be upgraded:
  postfix
1 upgraded, 0 newly installed, 0 to remove and 47 not upgraded.
Need to get 1149 kB of archives.
After this operation, 239 kB of additional disk space will be used.
Get:1 http://ppa.launchpad.net/ci-train-ppa-service/3415/ubuntu cosmic/main 
amd64 postfix amd64 3.3.0-1ubuntu2~test1 [1149 kB]
Fetched 1149 kB in 1s (845 kB/s)   
Preconfiguring packages ...
(Reading database ... 53910 files and directories currently installed.)
Preparing to unpack .../postfix_3.3.0-1ubuntu2~test1_amd64.deb ...
Unpacking postfix (3.3.0-1ubuntu2~test1) over (3.3.0-1ubuntu1) ...
Processing triggers for ufw (0.35-6) ...
Processing triggers for systemd (239-7ubuntu7) ...
Processing triggers for man-db (2.8.4-2) ...
Processing triggers for rsyslog (8.32.0-1ubuntu5) ...
Setting up postfix (3.3.0-1ubuntu2~test1) ...
Removing obsolete conffile /etc/postfix/makedefs.out ...

Postfix (main.cf) configuration was not changed.  If you need to make changes, 
edit /etc/postfix/main.cf (and others) as needed.  To view Postfix 
configuration values, see postconf(1).

After modifying main.cf, be sure to run 'service postfix reload'.

Processing triggers for libc-bin (2.28-0ubuntu1) ...
root@c:~# dpkg --status postfix | grep makedefs.out; ls -laF 
/etc/postfix/makedefs.out /usr/share/postfix/makedefs.out
lrwxrwxrwx 1 root root   31 Sep 14 06:58 /etc/postfix/makedefs.out -> 
/usr/share/postfix/makedefs.out
-rw-r--r-- 1 root root 4480 Sep 13 12:23 /usr/share/postfix/makedefs.out

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https://bugs.launchpad.net/bugs/1791853

Title:
  Postfix upgrade queries about replacing /etc/postfix/makedefs.out,
  when it really should always do so

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