The rootless Docker experience used to be pretty bad and it was less friction to use something that was rootless by default (like Podman). Has this changed?

it changed and its better now. rootless dockerd wants newuidmap/newgidmap + subuid range before it start, and cgroups only work with cgroup v2 + systemd. also, on a host that already has those, its fine on one without systemd, and podman is still less friction, mostly because there is no daemon to babysit

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