I can indeed trigger it in cosmic with an upgrade from 1:2.12+dfsg-3ubuntu8 -> 1:2.12+dfsg-3ubuntu8.6 But forcing the same (by enabling cosmics sources) in Disco does not trigger the bug (1.10ubuntu5). You will need an equiv trick to verify Disco as well I think. Here he logs of the cosmic verify: # trigger bug before upgrade /etc/qemu/fsfreeze-hook found conffile /etc/qemu/fsfreeze-hook in new pkg but on dpkg status An error occurred: [Errno 21] Is a directory: '/etc/qemu/fsfreeze-hook' Traceback (most recent call last): File "/usr/bin/unattended-upgrade", line 1669, in main install_start_time) File "/usr/bin/unattended-upgrade", line 1875, in run if conffile_prompt(item.destfile): File "/usr/bin/unattended-upgrade", line 1015, in conffile_prompt with open(prefix + conf_file, 'rb') as fp: IsADirectoryError: [Errno 21] Is a directory: '/etc/qemu/fsfreeze-hook' Extracting content from /var/log/unattended-upgrades/unattended-upgrades-dpkg.log since 2019-05-03 05:45:41 Traceback (most recent call last): File "/usr/bin/unattended-upgrade", line 2138, in sys.exit(main(options)) File "/usr/bin/unattended-upgrade", line 1669, in main install_start_time) File "/usr/bin/unattended-upgrade", line 1875, in run if conffile_prompt(item.destfile): File "/usr/bin/unattended-upgrade", line 1015, in conffile_prompt with open(prefix + conf_file, 'rb') as fp: IsADirectoryError: [Errno 21] Is a directory: '/etc/qemu/fsfreeze-hook' # upgrade to proposed apt install unattended-upgrades Reading package lists... Done Building dependency tree Reading state information... Done Suggested packages: bsd-mailx default-mta | mail-transport-agent needrestart The following packages will be upgraded: unattended-upgrades 1 upgraded, 0 newly installed, 0 to remove and 4 not upgraded. Need to get 41.8 kB of archives. After this operation, 0 B of additional disk space will be used. Get:1 http://archive.ubuntu.com/ubuntu cosmic-proposed/main amd64 unattended-upgrades all 1.5ubuntu3.18.10.4 [41.8 kB] Fetched 41.8 kB in 0s (535 kB/s) Preconfiguring packages ... (Reading database ... 46512 files and directories currently installed.) Preparing to unpack .../unattended-upgrades_1.5ubuntu3.18.10.4_all.deb ... Unpacking unattended-upgrades (1.5ubuntu3.18.10.4) over (1.5ubuntu3.18.10.3) ... Processing triggers for systemd (239-7ubuntu10.13) ... Setting up unattended-upgrades (1.5ubuntu3.18.10.4) ... Processing triggers for man-db (2.8.4-2) ... # retry with fix root@c:~# sudo unattended-upgrade -d Initial blacklisted packages: Initial whitelisted packages: Starting unattended upgrades script [...] check_conffile_prompt(/var/cache/apt/archives/qemu-guest-agent_1%3a2.12+dfsg-3ubuntu8.6_amd64.deb) found pkg: qemu-guest-agent conffile line: /etc/init.d/qemu-guest-agent f61a64ac1e48993023018fd1cff85191 current md5: f61a64ac1e48993023018fd1cff85191 conffile line: /etc/qemu/fsfreeze-hook/fsfreeze-hook 15f6ff42cbc5550a07ee21c2a471d905 current md5: 15f6ff42cbc5550a07ee21c2a471d905 blacklist: [] whitelist: [] Packages that will be upgraded: qemu-guest-agent Writing dpkg log to /var/log/unattended-upgrades/unattended-upgrades-dpkg.log applying set ['qemu-guest-agent'] (Reading database ... 46512 files and directories currently installed.) Preparing to unpack .../qemu-guest-agent_1%3a2.12+dfsg-3ubuntu8.6_amd64.deb ... Unpacking qemu-guest-agent (1:2.12+dfsg-3ubuntu8.6) over (1:2.12+dfsg-3ubuntu8) ... Setting up qemu-guest-agent (1:2.12+dfsg-3ubuntu8.6) ... Processing triggers for systemd (239-7ubuntu10.13) ... Processing triggers for man-db (2.8.4-2) ... left to upgrade set() All upgrades installed InstCount=0 DelCount=0 BrokenCount=0 Extracting content from /var/log/unattended-upgrades/unattended-upgrades-dpkg.log since 2019-05-03 05:49:31 Mark cosmic as verified