This page documents debugging a failed Ubuntu release upgrade that left the system unbootable. The root causes were an interplay between LUKS2 encryption, GRUB 2.12, Secure Boot and missing dotfiles — each amplifying the others into a long chain of cascading problems.
Starting Point Xubuntu 20.04, LUKS2-encrypted root partition Dual-boot with Windows on the same NVMe SSD A second encrypted partition (Veracrypt/exFAT) as shared storage, mounted at /home/user/data Personal dotfiles (xmonad, zsh, vim, etc.) stored as symlinks on this Veracrypt partition Neo2 keyboard layout, xmonad as window manager, Alacritty as terminal Phase 1: Failed Dist-Upgrade do-release-upgrade from 20.04 → 22.04 was started. The upgrade stalled on the package ConTeXt MarkIV (part of TeXLive) — a very large package whose post-install script runs for a long time. It was manually interrupted.