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sshdof modern OpenSSH enforces the restriction that theChrootDirectorymust be writeable by root only; if this is not true, the login will fail. If a chroot directory is writeable by the chrooted user, there are some known methods to escape from a chroot; the OpenSSH requirement to have a read-only ChrootDirectory is to block these escape methods.dpkg-query -Wshows the package version string as1:8.2p1-4ubuntu0.11. Is the "modern" OpenSSH you mention newer than that?