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I wonder what's missing from Debian to automate such things since my automation experience is mainly with RHEL. (I realize it may be partly a question of effort for automation, but it sounds as if that's not the root of it.)

Debian can restart processes dependent on updated packages and issue alerts about the need to, and you can automate checking for new releases of things for which you've done package backports. That doesn't finesse reboots for kernel updates and whatever systemd forces on you now, but I assume you can at least have live kernel patching as for the RHEL systems for which I used not to get system time.

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