[pkg-cryptsetup-devel] Bug#1140141: cryptsetup: Failure to boot fresh install via cryptroot-unlock with an encrypted home partition

[Alez]

I suppose you are right. Well, it was a remote installation over SSH for 
a headless system. Debian‐Installer in theory supports fully remote 
installation. After installation, in order to boot a headless system 
with encrypted drives, the key must be provided over SSH such as via 
dropbear. So I suppose the issue being unable to boot is particular to 
this use case with headless systems. It works just fine with only an 
encrypted root device, so I suppose I did not expect that additional 
devices would cause problems in Trixie (this set up works without any 
issue in previous versions of Debian). I had issues upgrading from 
Bookworm due to this (failed to boot after upgrading due to this and 
another separate change in behaviour), but the difference in behaviour 
from Bookworm's installation / debian‐installer tripped me up as from my 
point of view it appears to be a regression.


On Tue, 16 Jun 2026 18:14:04 +0200 Guilhem Moulin <guilhem at debian.org> 
wrote:

 > On Tue, 16 Jun 2026 at 10:38:29 -0500, Alez wrote:
 > > The installer should leave the computer in a bootable state.
 >
 > The computer is bootable isn't it? AFAIK remote unlocking isn't done by
 > the installer itself.
 >
 > --
 > Guilhem.
 >
 >