Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-24 Thread Michael Hudson-Doyle
On Wed, 24 Jan 2024 at 20:48, Adrien Nader  wrote:

> On Wed, Jan 24, 2024, Michael Hudson-Doyle wrote:
> > On Tue, 23 Jan 2024 at 02:31, Jeremy Bícha 
> > wrote:
> >
> > > On Mon, Jan 22, 2024 at 7:36 AM Dimitri John Ledkov
> > >  wrote:
> > > > > Sadly shipping this in 24.04 means that PPAs owned by user
> > > > > accounts created prior to 2014-03-11[3] until the key rotation
> > > > > mechanism(s) [4][5] have been implemented.
> > > > >
> > > >
> > > > I do wonder how many active old PPA owners remain in action.
> > > >
> > > > And if we can reset per-series signing keys on all of those for any
> > > > new PPAs, and noble series (meaning single signe, new key for
> noble+).
> > > >
> > > > I have personally created a new team for myself, only added myself to
> > > > be a member of said team, to gain access to PPAs signed with 4k RSA
> > > > key, as I can no longer use my own ppas. I guess I should ask to
> > > > delete them all, and request removal of the signing key to gain back
> > > > personal PPAs with 4k signing key.
> > >
> > > Many of Ubuntu's core teams are older than 2014. This includes
> > > Desktop, Checkbox, Kernel, Pythoneers, Security, Mozilla, LibreOffice,
> > > Kubuntu, Lubuntu.
> > >
> > > I suspect that this change would break most of the heaviest used PPAs.
> > > We need a coordinated transition.
> > >
> >
> > I agree with Jeremy that we can't just blithely assume all PPAs created
> > before 2014 are no longer much used.
> >
> > Unfortunately I don't know what that means for a way forward. Clearly
> 1024R
> > keys should be retired. From one angle, I can imagine a scheme were a
> repo
> > is dual-signed and signs the new key with the old to convince apt to
> update
> > it but from another this seems impossible (and clearly very unlikely to
> > land before noble GA).
>
> We know of at least one active PPA with a 1024-bit key:
> https://launchpad.net/~videolan/+archive/ubuntu/master-daily .
>

I kind of misspoke in a way -- it's not the PPA that has to be old, as all
PPAs from a given owner are signed with the same key. It sounds slightly
more tractable to have Launchpad generate new keys for each owner and sign
new PPAs with that key. But a) not in time for noble b) this doesn't really
solve the problem anyway.

Cheers,
mwh
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Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-24 Thread Jeremy Bícha
On Wed, Jan 24, 2024 at 2:48 AM Adrien Nader  wrote:
>
> On Wed, Jan 24, 2024, Michael Hudson-Doyle wrote:
> > On Tue, 23 Jan 2024 at 02:31, Jeremy Bícha 
> > wrote:
> >
> > > On Mon, Jan 22, 2024 at 7:36 AM Dimitri John Ledkov
> > >  wrote:
> > > > > Sadly shipping this in 24.04 means that PPAs owned by user
> > > > > accounts created prior to 2014-03-11[3] until the key rotation
> > > > > mechanism(s) [4][5] have been implemented.
> > > > >
> > > >
> > > > I do wonder how many active old PPA owners remain in action.
> > > >
> > > > And if we can reset per-series signing keys on all of those for any
> > > > new PPAs, and noble series (meaning single signe, new key for noble+).
> > > >
> > > > I have personally created a new team for myself, only added myself to
> > > > be a member of said team, to gain access to PPAs signed with 4k RSA
> > > > key, as I can no longer use my own ppas. I guess I should ask to
> > > > delete them all, and request removal of the signing key to gain back
> > > > personal PPAs with 4k signing key.
> > >
> > > Many of Ubuntu's core teams are older than 2014. This includes
> > > Desktop, Checkbox, Kernel, Pythoneers, Security, Mozilla, LibreOffice,
> > > Kubuntu, Lubuntu.
> > >
> > > I suspect that this change would break most of the heaviest used PPAs.
> > > We need a coordinated transition.
> > >
> >
> > I agree with Jeremy that we can't just blithely assume all PPAs created
> > before 2014 are no longer much used.
> >
> > Unfortunately I don't know what that means for a way forward. Clearly 1024R
> > keys should be retired. From one angle, I can imagine a scheme were a repo
> > is dual-signed and signs the new key with the old to convince apt to update
> > it but from another this seems impossible (and clearly very unlikely to
> > land before noble GA).
>
> We know of at least one active PPA with a 1024-bit key:
> https://launchpad.net/~videolan/+archive/ubuntu/master-daily .

There are many more active 1024-bit PPAs. In my earlier reply. I
listed several teams that have 1024 bit keys. Some of those teams use
their PPAs for mostly development series work like Pythoneers and this
change may not be disruptive. For others, the PPA is an important
component of what they offer the community: like Kubuntu and Lubuntu.

Thank you,
Jeremy Bícha

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Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-24 Thread Adrien Nader
On Wed, Jan 24, 2024, Michael Hudson-Doyle wrote:
> On Tue, 23 Jan 2024 at 02:31, Jeremy Bícha 
> wrote:
> 
> > On Mon, Jan 22, 2024 at 7:36 AM Dimitri John Ledkov
> >  wrote:
> > > > Sadly shipping this in 24.04 means that PPAs owned by user
> > > > accounts created prior to 2014-03-11[3] until the key rotation
> > > > mechanism(s) [4][5] have been implemented.
> > > >
> > >
> > > I do wonder how many active old PPA owners remain in action.
> > >
> > > And if we can reset per-series signing keys on all of those for any
> > > new PPAs, and noble series (meaning single signe, new key for noble+).
> > >
> > > I have personally created a new team for myself, only added myself to
> > > be a member of said team, to gain access to PPAs signed with 4k RSA
> > > key, as I can no longer use my own ppas. I guess I should ask to
> > > delete them all, and request removal of the signing key to gain back
> > > personal PPAs with 4k signing key.
> >
> > Many of Ubuntu's core teams are older than 2014. This includes
> > Desktop, Checkbox, Kernel, Pythoneers, Security, Mozilla, LibreOffice,
> > Kubuntu, Lubuntu.
> >
> > I suspect that this change would break most of the heaviest used PPAs.
> > We need a coordinated transition.
> >
> 
> I agree with Jeremy that we can't just blithely assume all PPAs created
> before 2014 are no longer much used.
> 
> Unfortunately I don't know what that means for a way forward. Clearly 1024R
> keys should be retired. From one angle, I can imagine a scheme were a repo
> is dual-signed and signs the new key with the old to convince apt to update
> it but from another this seems impossible (and clearly very unlikely to
> land before noble GA).

We know of at least one active PPA with a 1024-bit key:
https://launchpad.net/~videolan/+archive/ubuntu/master-daily .

On the other hand, we can probably imagine there are only a few of them.
How do we do a large-scale analysis however? Actually, I think I spotted
something in launchpadlib but I haven't used that library yet and would
have to spend time discovering it.

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Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-23 Thread Michael Hudson-Doyle
On Tue, 23 Jan 2024 at 02:31, Jeremy Bícha 
wrote:

> On Mon, Jan 22, 2024 at 7:36 AM Dimitri John Ledkov
>  wrote:
> > > Sadly shipping this in 24.04 means that PPAs owned by user
> > > accounts created prior to 2014-03-11[3] until the key rotation
> > > mechanism(s) [4][5] have been implemented.
> > >
> >
> > I do wonder how many active old PPA owners remain in action.
> >
> > And if we can reset per-series signing keys on all of those for any
> > new PPAs, and noble series (meaning single signe, new key for noble+).
> >
> > I have personally created a new team for myself, only added myself to
> > be a member of said team, to gain access to PPAs signed with 4k RSA
> > key, as I can no longer use my own ppas. I guess I should ask to
> > delete them all, and request removal of the signing key to gain back
> > personal PPAs with 4k signing key.
>
> Many of Ubuntu's core teams are older than 2014. This includes
> Desktop, Checkbox, Kernel, Pythoneers, Security, Mozilla, LibreOffice,
> Kubuntu, Lubuntu.
>
> I suspect that this change would break most of the heaviest used PPAs.
> We need a coordinated transition.
>

I agree with Jeremy that we can't just blithely assume all PPAs created
before 2014 are no longer much used.

Unfortunately I don't know what that means for a way forward. Clearly 1024R
keys should be retired. From one angle, I can imagine a scheme were a repo
is dual-signed and signs the new key with the old to convince apt to update
it but from another this seems impossible (and clearly very unlikely to
land before noble GA).

Cheers,
mwh
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Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-23 Thread Brian Murray
On Thu, Jan 18, 2024 at 07:01:48PM +0100, Julian Andres Klode wrote:
> Hi,
> 
> we just noticed again that we are still trusting 1024R keys for
> signing repositories in APT, arguably because we do not have a
> means to tell gpgv the minimum key size.
> 
> While the upstream bug[0] is being worked on,
> I have written a hack[1] that - if APT_SIGNING_REQUIREMENTS_HACK
> environment variable is set - makes gpgv error out on keys smaller
> than 2048R and warn on keys smaller than 3072R (following the
> current OpenPGP draft size length requirements, 3072 is a SHOULD,
> 2048 a MUST).
> 
> I have also written code in APT to actually parse GPG error and
> warning status messages, and set the environment variable.[2]
> 
> Sadly shipping this in 24.04 means that PPAs owned by user
> accounts created prior to 2014-03-11[3] until the key rotation
> mechanism(s) [4][5] have been implemented.

I think there is a word missing in the above paragraph. What
specifically will happen to PPAs owned by user accounts created prior to
2014-03-11?

Thanks,
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Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-22 Thread Jeremy Bícha
On Mon, Jan 22, 2024 at 7:36 AM Dimitri John Ledkov
 wrote:
> > Sadly shipping this in 24.04 means that PPAs owned by user
> > accounts created prior to 2014-03-11[3] until the key rotation
> > mechanism(s) [4][5] have been implemented.
> >
>
> I do wonder how many active old PPA owners remain in action.
>
> And if we can reset per-series signing keys on all of those for any
> new PPAs, and noble series (meaning single signe, new key for noble+).
>
> I have personally created a new team for myself, only added myself to
> be a member of said team, to gain access to PPAs signed with 4k RSA
> key, as I can no longer use my own ppas. I guess I should ask to
> delete them all, and request removal of the signing key to gain back
> personal PPAs with 4k signing key.

Many of Ubuntu's core teams are older than 2014. This includes
Desktop, Checkbox, Kernel, Pythoneers, Security, Mozilla, LibreOffice,
Kubuntu, Lubuntu.

I suspect that this change would break most of the heaviest used PPAs.
We need a coordinated transition.

Thank you,
Jeremy Bícha

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Re: Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-22 Thread Dimitri John Ledkov
Hi,

On Thu, 18 Jan 2024 at 18:02, Julian Andres Klode
 wrote:
>
> Hi,
>
> we just noticed again that we are still trusting 1024R keys for
> signing repositories in APT, arguably because we do not have a
> means to tell gpgv the minimum key size.
>
> While the upstream bug[0] is being worked on,
> I have written a hack[1] that - if APT_SIGNING_REQUIREMENTS_HACK
> environment variable is set - makes gpgv error out on keys smaller
> than 2048R and warn on keys smaller than 3072R (following the
> current OpenPGP draft size length requirements, 3072 is a SHOULD,
> 2048 a MUST).

Separately we also care about NIST FIPS recommendations, for RSA it is
2048 until 2030, and with an option to bump it to 3072 from 2030.
Thus one can scope this as 2048 until 2030, and 3072 from 2030 already.

Also, given the performance penalty involved we should also consider
to support and accept ECC - as per NIST Ed25519 (more popular in new
deployments) is now approved as is P-256 (wider compat and support)
both of which are post-2030 acceptable to NIST, the wider internet
(TLS authorities) and us.

>
> I have also written code in APT to actually parse GPG error and
> warning status messages, and set the environment variable.[2]
>
> Sadly shipping this in 24.04 means that PPAs owned by user
> accounts created prior to 2014-03-11[3] until the key rotation
> mechanism(s) [4][5] have been implemented.
>

I do wonder how many active old PPA owners remain in action.

And if we can reset per-series signing keys on all of those for any
new PPAs, and noble series (meaning single signe, new key for noble+).

I have personally created a new team for myself, only added myself to
be a member of said team, to gain access to PPAs signed with 4k RSA
key, as I can no longer use my own ppas. I guess I should ask to
delete them all, and request removal of the signing key to gain back
personal PPAs with 4k signing key.

> However given that (I've been informed) ~800 bits were already cracked about 
> 5 years
> ago, and we are planning to support 24.04 for 12 years, I believe
> that this is necessary and it's better to take the pain now then
> do an SRU to disable 1024R keys on existing systems.
>
> This is more painful than the digest transition because we have
> reason to believe that 1024R keys are potentially unsafe *now*
> and we need to stop trusting them, whereas when we deprecated
> MD5 and SHA1 we were able to have a deprecation period of a
> stable release.
>
> [0] https://dev.gnupg.org/T6946
> [1] https://gist.github.com/julian-klode/fbc56278cd0bdcd305f825479b094fad
> [2] https://salsa.debian.org/apt-team/apt/-/merge_requests/322
> [3] https://code.launchpad.net/~wgrant/launchpad/4096r-ppa-keys/+merge/210336
> [4] https://bugs.launchpad.net/launchpad/+bug/1331914
> [5] https://bugs.launchpad.net/ubuntu/+source/apt/+bug/1461834
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Bumping apt RSA key length requirements to 3072-bit (2048 w/ warning) for 24.04

2024-01-18 Thread Julian Andres Klode
Hi,

we just noticed again that we are still trusting 1024R keys for
signing repositories in APT, arguably because we do not have a
means to tell gpgv the minimum key size.

While the upstream bug[0] is being worked on,
I have written a hack[1] that - if APT_SIGNING_REQUIREMENTS_HACK
environment variable is set - makes gpgv error out on keys smaller
than 2048R and warn on keys smaller than 3072R (following the
current OpenPGP draft size length requirements, 3072 is a SHOULD,
2048 a MUST).

I have also written code in APT to actually parse GPG error and
warning status messages, and set the environment variable.[2]

Sadly shipping this in 24.04 means that PPAs owned by user
accounts created prior to 2014-03-11[3] until the key rotation
mechanism(s) [4][5] have been implemented.

However given that (I've been informed) ~800 bits were already cracked about 5 
years
ago, and we are planning to support 24.04 for 12 years, I believe
that this is necessary and it's better to take the pain now then
do an SRU to disable 1024R keys on existing systems.

This is more painful than the digest transition because we have
reason to believe that 1024R keys are potentially unsafe *now*
and we need to stop trusting them, whereas when we deprecated
MD5 and SHA1 we were able to have a deprecation period of a
stable release.

[0] https://dev.gnupg.org/T6946
[1] https://gist.github.com/julian-klode/fbc56278cd0bdcd305f825479b094fad
[2] https://salsa.debian.org/apt-team/apt/-/merge_requests/322
[3] https://code.launchpad.net/~wgrant/launchpad/4096r-ppa-keys/+merge/210336
[4] https://bugs.launchpad.net/launchpad/+bug/1331914
[5] https://bugs.launchpad.net/ubuntu/+source/apt/+bug/1461834
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