Why Operating Systems don't always upgrade GnuPG [was: Re: How can we utilize latest GPG from RPM repository?]

edgar at pettijohn-web.com edgar at pettijohn-web.com
Mon Feb 19 21:51:08 CET 2018

On Feb 19, 2018 12:45 PM, Daniel Kahn Gillmor <dkg at fifthhorseman.net> wrote:
> On Sat 2018-02-17 17:06:54 -0600, helices wrote:
> > I will probably never understand why wanting to run the most current
> > version of gnupg on a plethora of servers is controversial.
> Here's one last try to explain the situation.
> GnuPG (and the libraries it depends on) are used by (aka "depended on
> by") other libraries and tools, both those integrated into the operating
> system itself, and those that might be externally installed.  Some of
> these dependencies are "brittle".
> Brittle software dependencies
> -----------------------------
> GnuPG is under active development, and it has never had a fully-featured
> stable API (Application Programming Interface).  What i mean is, there
> are some capabilities that are only available from the user interface
> (UI), and are not in the stable API.  GnuPG's UI has been constantly
> improving; sometimes that means that older (worse) UI gets deprecated,
> removed, or has its semantics change.
> For historical reasons, there are a number of tools that were built
> around some element of the GnuPG UI that was current at the time the
> tool was built.  Even worse, there are a number of tools that assume
> certain behaviors and features of GnuPG's internal storage (e.g. what
> goes on in ~/.gnupg/), which has never been explicitly part of its API
> (confusingly, there are some exceptions where GnuPG upstream *has*
> encouraged other tools to programmatically interact with some elements
> within its internal storage).  Newer versions of GnuPG do different
> things with its internal storage (and as users we get benefits from
> those improvements).
> Simply upgrading GnuPG to the latest available version on a server that
> also ships other complex software is likely to lead to breakage
> elsewhere in the OS because of these brittle assumptions and
> dependencies around GnuPG's UI and internal storage.
> A case study
> ------------
> For example, the current stable version of the Debian operating system
> is Debian 9 ("stretch"), and it ships a version of the "modern" branch
> of GnuPG.
> As one of the GnuPG maintainers for Debian, i was hoping at one point to
> backport the "modern" version of GnuPG to the previous version of Debian
> (Debian 8, "jessie"), which some people still run on servers.  I found
> that such an upgrade would break at least a half-dozen other packages in
> Debian jessie *that i knew of* [0] -- and their breakage would in turn
> likely affect some number of other packages.  This was not an exhaustive
> survey of all possible bugs, just the most visible ones. :/
> I have personally given up on the project of backporting modern GnuPG to
> "jessie", because i think what time i can devote to GnuPG maintenance is
> better-spent elsewhere.  I don't have the bandwidth to cope with the
> resultant bug reports in other packages that such a backport would
> produce.  Generally, i encourage users of "jessie" to uprade their
> entire OS to the current version of debian stable, and to take advantage
> of the improvements to GnuPG that way.
> What can we do?
> ---------------
> The problems described above point to problems in the ecosystem *around*
> GnuPG, but it also points to concerns about GnuPG's presentation of its
> capabilities *to* the rest of the ecosystem.  To the extent that GnuPG
> offers features that other tools might want to use, when those features
> are not part of an explicit, documented API, the ecosystem apparently
> *does* try to manipulate them anyway, with all the attendant brittleness
> that you can imagine.
> How can GnuPG contribute to fixing this problem?  The traditional way
> that many other projects have taken is to define their core programmatic
> functionality into a library with a strict interface guarantees, and
> have explicitly deprecated other use.  The closest that GnuPG comes to
> this technique is GPGME, which is not feature-complete (as compared to
> the gpg executable), and has its own history of both difficult upgrades
> and unclear/surprising semantics.  It also doesn't have bindings in many
> popular programming languages.  When programmers in those language want
> to use GnuPG, their shortest path to "something that works" often
> involves shelling out to gpg, rather than binding to GPGME. :/ 

That doesn't sound secure. Probably shouldn't use such programs on a server. Gpgme looks to do everything that it needs to do. Can you specify a function it is missing? 

> Another thing that would help would be to explicitly and succinctly
> document the preferred ways of interacting with GnuPG in ways that other
> developers find useful.  Perhaps GnuPG could also itself try to detect
> when it is being used programmatically in an unstable way and produce
> warnings?
> Yet another complementary approach might be to aggressively police the
> ecosystem by finding other software that deends on GnuPG in any of the
> aforementioned brittle ways, and either ask those developers to stop
> using GnuPG entirely, or to provide them with stable, well-supported
> ways to do what they're looking to do.

I think gpgme is the answer here as well. If you mean specifically a python interface to gpgme then it's probably up to a python developer to get that rolling.

> I welcome discussion/suggestions on how we can improve this situation,
> and i *definitely* welcome help in doing the kind of
> ecosystem-perspective work necessary to make it easier to maintain an
> up-to-date branch of GnuPG.
> But shrugging and suggesting it's uncontroversial to upgrade arbitrary
> machines to the latest version of GnuPG doesn't appreciate the scope of
> the problem involved with software maintenance in an active and
> interdependent ecosystem.
> Regards,
>         --dkg
> [0] examples of breakage:
>   https://bugs.debian.org/834281
>   https://bugs.debian.org/835075
>   https://bugs.debian.org/835592
>   https://bugs.debian.org/835465
>   https://bugs.debian.org/834514
>   https://bugs.debian.org/834600
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