X-Debbugs-CC: Martin-Éric Racine <martin-eric.rac...@iki.fi> A couple of observations:
* You have tpm2-abrmd installed, and its systemd unit is the only one defining a Requires=systemd-udev-settle.service. 2.1.0-1 under Buster didn't do that yet, so this could be the breaking change. As its manpage states systemd-udev-settle.service as a unit is conceptually problematic because udev events are never really settled; the unit is also deprecated, so tpm2-abrmd should correct its systemd/udev definitions. * Another potential issue is this line: post-up systemctl restart micro-httpd.socket The call to systemctl might be blocking. * Both ifupdown-pre.service and systemd-udev-settle.service run "udevadm settle" in ExecStart= * These dependencies are defined: systemd-udev-trigger.service: Before=systemd-udev-settle.service ifupdown-pre.service: After=systemd-udev-trigger.service systemd-udev-settle.service: After=systemd-udev-trigger.service sysinit.target: After=systemd-udev-settle.service micro-httpd.socket: {After,Requires}=sysinit.target I wonder if that micro-httpd.socket definition amounts to a circular dependency resulting in a deadlock. I recommend uncommenting the post-up line from /etc/network/interfaces just to see if this solves the problem. Alternatively try disabling tpm2-abrmd.service temporarily. Regards, Dennis.