Hi Guilhem,

Thanks for getting back to me, I have raised a bug with the format provided 
below, I believe the issue is in cryptsetup as this was updated during the time 
between not having the issue and it appearing. Where, as far as I can tell, 
dropbear was not patched.

Package: cryptsetup 
Version:2:2.1.0

Error message is;
Error: Timeout reached while waiting for askpass

Command run is;
cryptroot-unlock

kernel is;
4.19.37-5

C version;
2.28-10

I am pretty sure that the upgrade from cryptsetup 2:2.0.6 to the version above 
caused this issue.

Kind regards,

Luke Flinders

-----Original Message-----
From: Guilhem Moulin <guil...@fripost.org> 
Sent: 09 July 2019 13:32
To: Luke Flinders <lflind...@ip-performance.co.uk>
Cc: dropbear@ucc.asn.au; Andy Millett <amill...@ip-performance.co.uk>
Subject: Re: Cryptroot-unlock Timeout on askpass

Hi,

On Tue, 09 Jul 2019 at 09:02:53 +0000, Luke Flinders wrote:
> We have had the remote decrypting functioning for a while, however 
> following recent updates to Debian it has now stopped working.
> […]
> I have had a look through your mailing archive and can not see this 
> issue mentioned anywhere.

That feature isn't developed nor maintained by dropbear's upstream maintainer, 
but by the Debian package maintainer (who happens to be me right now).  Could 
please you file a bug against the ‘dropbear-initramfs’
package (or the ‘cryptsetup-initramfs’ package if you believe the problem is in 
`cryptroot-look`) at the Debian BTS? https://bugs.debian.org/

We'll likely need some details about your setup.  reportbug(1) will 
automatically fill a template with the relevant details.

Thanks!
Cheers,
--
Guilhem.

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