An attempt to reproduce - partially successful, maybe reveals deeper issues!
su - mkdir /tmp/bullseye cd /tmp/bullseye debootstrap bullseye . https://deb.debian.org/debian chroot . apt install emacs elpa-helpful sed -i s/bullseye/bookworm/ ./etc/apt/sources.list chroot . apt update chroot . apt upgrade # This fails with: Setting up tasksel-data (3.73) ... [15/1797] Setting up emacs-common (1:28.2+1-15) ... Setting up emacs-bin-common (1:28.2+1-15) ... Setting up emacs-gtk (1:28.2+1-15) ... tsort: -: input contains a loop: tsort: elpa-dash tsort: emacsen-common tsort: -: input contains a loop: tsort: elpa-s tsort: emacsen-common Install elpa-dash for emacs install/dash-2.19.1: Handling install of emacsen flavor emacs install/dash-2.19.1: byte-compiling for emacs >>Error occurred processing dash.el: File error (("Doing chmod" "Operation not >>supported" "/usr/share/emacs/site-lisp/elpa/dash-2.19.1/dash. elceCdFwM")) ERROR: install script from elpa-dash package failed dpkg: error processing package emacs-gtk (--configure): installed emacs-gtk package post-installation script subprocess returned error exit status 1 dpkg: dependency problems prevent configuration of emacs: emacs depends on emacs-gtk (>= 1:27.1) | emacs-lucid (>= 1:27.1) | emacs-nox (>= 1:27.1); however: Package emacs-gtk is not configured yet. Package emacs-lucid is not installed. Package emacs-nox is not installed. dpkg: error processing package emacs (--configure): dependency problems - leaving unconfigured Processing triggers for hicolor-icon-theme (0.17-2) ... Processing triggers for libc-bin (2.36-9+deb12u1) ... Processing triggers for debianutils (5.7-0.4) ... Processing triggers for install-info (6.8-6+b1) ... Processing triggers for ca-certificates (20230311) ... Updating certificates in /etc/ssl/certs... 0 added, 0 removed; done. Running hooks in /etc/ca-certificates/update.d... done. Processing triggers for libgdk-pixbuf-2.0-0:amd64 (2.42.10+dfsg-1+b1) ... Errors were encountered while processing: emacs-gtk emacs E: Sub-process /usr/bin/dpkg returned an error code (1) BUT, /tmp/bullseye/usr/share/emacs/site-lisp/elpa/helpful-0.18/ has the broken symlinks - and presumably should not exist at all. so maybe this helps narrow it down!