I only have a testcase for Bionic, I hope rbalint has one for the other releases. root@b:~# apt list --upgradable Listing... Done qemu-guest-agent/bionic-updates,bionic-security 1:2.11+dfsg-1ubuntu7.12 amd64 [upgradable from: 1:2.11+dfsg-1ubuntu7] N: There is 1 additional version. Please use the '-a' switch to see it root@b:~# root@b:~# root@b:~# sudo unattended-upgrade -d Initial blacklisted packages: Initial whitelisted packages: Starting unattended upgrades script Allowed origins are: o=Ubuntu,a=bionic, o=Ubuntu,a=bionic-security, o=UbuntuESM,a=bionic Using (^linux-image-[0-9]+\.[0-9\.]+-.*|^linux-headers-[0-9]+\.[0-9\.]+-.*|^linux-image-extra-[0-9]+\.[0-9\.]+-.*|^linux-modules-[0-9]+\.[0-9\.]+-.*|^linux-modules-extra-[0-9]+\.[0-9\.]+-.*|^linux-signed-image-[0-9]+\.[0-9\.]+-.*|^kfreebsd-image-[0-9]+\.[0-9\.]+-.*|^kfreebsd-headers-[0-9]+\.[0-9\.]+-.*|^gnumach-image-[0-9]+\.[0-9\.]+-.*|^.*-modules-[0-9]+\.[0-9\.]+-.*|^.*-kernel-[0-9]+\.[0-9\.]+-.*|^linux-backports-modules-.*-[0-9]+\.[0-9\.]+-.*|^linux-modules-.*-[0-9]+\.[0-9\.]+-.*|^linux-tools-[0-9]+\.[0-9\.]+-.*|^linux-cloud-tools-[0-9]+\.[0-9\.]+-.*) regexp to find kernel packages Using (^linux-image-4\.15\.0\-48\-generic$|^linux-headers-4\.15\.0\-48\-generic$|^linux-image-extra-4\.15\.0\-48\-generic$|^linux-modules-4\.15\.0\-48\-generic$|^linux-modules-extra-4\.15\.0\-48\-generic$|^linux-signed-image-4\.15\.0\-48\-generic$|^kfreebsd-image-4\.15\.0\-48\-generic$|^kfreebsd-headers-4\.15\.0\-48\-generic$|^gnumach-image-4\.15\.0\-48\-generic$|^.*-modules-4\.15\.0\-48\-generic$|^.*-kernel-4\.15\.0\-48\-generic$|^linux-backports-modules-.*-4\.15\.0\-48\-generic$|^linux-modules-.*-4\.15\.0\-48\-generic$|^linux-tools-4\.15\.0\-48\-generic$|^linux-cloud-tools-4\.15\.0\-48\-generic$) regexp to find running kernel packages Checking: qemu-guest-agent ([, ]) pkgs that look like they should be upgraded: qemu-guest-agent Get:1 http://archive.ubuntu.com/ubuntu bionic-updates/universe amd64 qemu-guest-agent amd64 1:2.11+dfsg-1ubuntu7.12 [232 kB] Fetched 232 kB in 0s (0 B/s) fetch.run() result: 0 check_conffile_prompt(/var/cache/apt/archives/qemu-guest-agent_1%3a2.11+dfsg-1ubuntu7.12_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 /etc/qemu/fsfreeze-hook/fsfreeze-hook not in package conffiles /etc/init.d/qemu-guest-agent /etc/qemu/fsfreeze-hook found conffile /etc/qemu/fsfreeze-hook in new pkg but on dpkg status Traceback (most recent call last): File "/usr/bin/unattended-upgrade", line 2057, in sys.exit(main(options)) File "/usr/bin/unattended-upgrade", line 1773, in main if conffile_prompt(item.destfile): File "/usr/bin/unattended-upgrade", line 988, in conffile_prompt with open(prefix + conf_file, 'rb') as fp: IsADirectoryError: [Errno 21] Is a directory: '/etc/qemu/fsfreeze-hook' That is good, it means that the error is affecting this system. After installing the new unattended upgrades from proposed this works fine now: root@b:~# apt list --upgradable Listing... Done qemu-guest-agent/bionic-updates,bionic-security 1:2.11+dfsg-1ubuntu7.12 amd64 [upgradable from: 1:2.11+dfsg-1ubuntu7] N: There is 1 additional version. Please use the '-a' switch to see it root@b:~# sudo unattended-upgrade -d Initial blacklisted packages: Initial whitelisted packages: Starting unattended upgrades script Allowed origins are: o=Ubuntu,a=bionic, o=Ubuntu,a=bionic-security, o=UbuntuESM,a=bionic Using (^linux-image-[0-9]+\.[0-9\.]+-.*|^linux-headers-[0-9]+\.[0-9\.]+-.*|^linux-image-extra-[0-9]+\.[0-9\.]+-.*|^linux-modules-[0-9]+\.[0-9\.]+-.*|^linux-modules-extra-[0-9]+\.[0-9\.]+-.*|^linux-signed-image-[0-9]+\.[0-9\.]+-.*|^kfreebsd-image-[0-9]+\.[0-9\.]+-.*|^kfreebsd-headers-[0-9]+\.[0-9\.]+-.*|^gnumach-image-[0-9]+\.[0-9\.]+-.*|^.*-modules-[0-9]+\.[0-9\.]+-.*|^.*-kernel-[0-9]+\.[0-9\.]+-.*|^linux-backports-modules-.*-[0-9]+\.[0-9\.]+-.*|^linux-modules-.*-[0-9]+\.[0-9\.]+-.*|^linux-tools-[0-9]+\.[0-9\.]+-.*|^linux-cloud-tools-[0-9]+\.[0-9\.]+-.*) regexp to find kernel packages Using (^linux-image-4\.15\.0\-48\-generic$|^linux-headers-4\.15\.0\-48\-generic$|^linux-image-extra-4\.15\.0\-48\-generic$|^linux-modules-4\.15\.0\-48\-generic$|^linux-modules-extra-4\.15\.0\-48\-generic$|^linux-signed-image-4\.15\.0\-48\-generic$|^kfreebsd-image-4\.15\.0\-48\-generic$|^kfreebsd-headers-4\.15\.0\-48\-generic$|^gnumach-image-4\.15\.0\-48\-generic$|^.*-modules-4\.15\.0\-48\-generic$|^.*-kernel-4\.15\.0\-48\-generic$|^linux-backports-modules-.*-4\.15\.0\-48\-generic$|^linux-modules-.*-4\.15\.0\-48\-generic$|^linux-tools-4\.15\.0\-48\-generic$|^linux-cloud-tools-4\.15\.0\-48\-generic$) regexp to find running kernel packages Checking: qemu-guest-agent ([, ]) pkgs that look like they should be upgraded: qemu-guest-agent Fetched 0 B in 0s (0 B/s) fetch.run() result: 0 check_conffile_prompt(/var/cache/apt/archives/qemu-guest-agent_1%3a2.11+dfsg-1ubuntu7.12_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 ... 47684 files and directories currently installed.) Preparing to unpack .../qemu-guest-agent_1%3a2.11+dfsg-1ubuntu7.12_amd64.deb ... Unpacking qemu-guest-agent (1:2.11+dfsg-1ubuntu7.12) over (1:2.11+dfsg-1ubuntu7) ... Processing triggers for ureadahead (0.100.0-21) ... Setting up qemu-guest-agent (1:2.11+dfsg-1ubuntu7.12) ... Processing triggers for systemd (237-3ubuntu10.21) ... Processing triggers for man-db (2.8.3-2ubuntu0.1) ... 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 2019-04-30 11:16:20 root@b:~# apt list --upgradable Listing... Done Setting Bionic to verified.