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 <[email protected]> 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.
>
>

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