I am using a bento/ubuntu18.04 box on vagrant/kitchen-ci with the kitchen-ansible provisioner and can reproduce this bug.
Setting up python-idna (2.6-1) ... Setting up python-yaml (3.12-1build2) ... Setting up python-asn1crypto (0.24.0-1) ... Setting up python-pyasn1 (0.4.2-3) ... Setting up python-pkg-resources (39.0.1-2) ... Setting up python-markupsafe (1.0-1build1) ... Setting up python-httplib2 (0.9.2+dfsg-1ubuntu0.1) ... Setting up python-cffi-backend (1.11.5-1) ... Setting up python-six (1.11.0-2) ... Processing triggers for libc-bin (2.27-3ubuntu1) ... Setting up sshpass (1.06-1) ... Setting up libssl1.1:amd64 (1.1.1-1ubuntu2.1~18.04.2) ... Checking for services that may need to be restarted...done. Checking for services that may need to be restarted...done. Checking init scripts... dpkg: error processing package libssl1.1:amd64 (--configure): installed libssl1.1:amd64 package post-installation script subprocess returned error exit status 10 Setting up python-enum34 (1.1.6-2) ... dpkg: dependency problems prevent configuration of python-cryptography: python-cryptography depends on libssl1.1 (>= 1.1.1); however: Package libssl1.1:amd64 is not configured yet. dpkg: error processing package python-cryptography (--configure): dependency problems - leaving unconfigured Processing triggers for man-db (2.8.3-2ubuntu0.1) ...No apport report written because the error message indicates its a followup error from a previous failure. Setting up python-ipaddress (1.0.17-1) ... Setting up python-setuptools (39.0.1-2) ... Setting up python-jinja2 (2.10-1ubuntu0.18.04.1) ... dpkg: dependency problems prevent configuration of libssl-dev:amd64: libssl-dev:amd64 depends on libssl1.1 (= 1.1.1-1ubuntu2.1~18.04.2); however: Package libssl1.1:amd64 is not configured yet. dpkg: error processing package libssl-dev:amd64 (--configure): dependency problems - leaving unconfigured dpkg: dependency problems prevent configuration of python-paramiko:No apport report written because the error message indicates its a followup error from a previous failure The fix works, this has only been an issue since 14th July 2019. -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to openssl in Ubuntu. https://bugs.launchpad.net/bugs/1832919 Title: installed libssl1.1:amd64 package post-installation script subprocess returned error exit status 10 Status in openssl package in Ubuntu: Incomplete Bug description: The error happens when trying to configure libssl1.1:amd64 (dpkg --configure -D 20000 libssl1.1) dpkg: error processing package libssl1.1:amd64 (--configure): installed libssl1.1:amd64 package post-installation script subprocess returned error exit status 10 D020000: post_script_tasks - ensure_diversions D020000: post_script_tasks - trig_incorporate D020000: check_triggers_cycle pnow=libc-bin:amd64 first Processing triggers for libc-bin (2.27-3ubuntu1) ... D020000: post_postinst_tasks - trig_incorporate Errors were encountered while processing: libssl1.1:amd64 [ WORKAROUND TO RECOVER YOUR SYSTEM ] $ sudo dpkg-reconfigure libc6 $ sudo dpkg --configure libssl1.1 [ Reproducer steps ] # DO NOT DO THIS ON PRODUCTION MACHINES # # echo PURGE | debconf-communicate libpam0g:amd64 0 # echo PURGE | debconf-communicate libpam0g 0 # echo PURGE | debconf-communicate libc6:amd64 0 # echo PURGE | debconf-communicate libc6 0 # sh -x /var/lib/dpkg/info/libssl1.1\:amd64.postinst configure 1.1.1 + . /usr/share/debconf/confmodule + [ ! ] + PERL_DL_NONLAZY=1 + export PERL_DL_NONLAZY + [ ] + exec /usr/share/debconf/frontend /var/lib/dpkg/info/libssl1.1:amd64.postinst configure 1.1.1 Checking for services that may need to be restarted...done. Checking for services that may need to be restarted...done. Checking init scripts... # echo $? 10 To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssl/+bug/1832919/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp