Hmm. As far as the installer goes, having the debian-installer mark the device with |x-initrd.attach| which appears to have similar functionality (systemd fomat) but not |initramfs| seems like an oversight or a bug in itself. The installer should leave the computer in a bootable state. I suppose the installer should either also add the |initramfs| option, or else the |x-initrd.attach |flag it already adds should produce similar behaviour for the purposes of determining drives required at initramfs time.

On Tue, 16 Jun 2026 16:07:46 +0200 Guilhem Moulin <[email protected]> wrote:

> Hi,
>
> On Tue, 16 Jun 2026 at 08:02:47 -0500, Alex wrote:
> > I created a fresh install of Debian Trixie with the installation media. During the installation, I created a separate partition for /home in a LUKS encrypted device. > > Upon booting for the first time, I could unlock these devices and boot normally by interacting directly with the physical computer, but when attempting to log in remotely via dropbear and unlock with cryptroot-unlock, I was unable to do so successfully (I was not prompted to unlock the /home device).
> >
> > I tested with only an encrypted /root separate from /boot. Using the same procedure, I was able to successfully boot using dropbear and cryptroot-unlock in this case.
> >
> > It appears that cryptroot-unlock does not properly prompt for all required boot devices even when booting can take place correctly via the normal terminal when interacting directly with the physical computer.
>
> cryptroot-unlock processes only devices that are configured for
> unlocking at initramfs stage there. Either because they are required
> (the device is holding the root file system, /usr, or the resume
> device), or because they have been manually configured with the
> `initramfs` crypttab(5) option.
>
> It appears your device is not configured to be unlocked at initramfs
> stage. When at the computer (not remotely), the unlocking happens by
> systemd later in the boot process. Use the `initramfs` crypttab(5)
> option and rebuild the initramfs if you want to unlock it at initramfs
> stage instead.
>
> --
> Guilhem.

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