GLEP 57: Security of distribution of Gentoo software - Overview

Author Robin Hugh Johnson <>
Type Informational
Status Final
Version 1
Created 2008-10-22
Last modified 2015-01-12
Posting history 2009-12-01
GLEP source glep-0057.rst


This is the first in a series of 4 GLEPs. It aims to define the actors and problems in the Gentoo software distribution process, with a strong emphasis on security. The concepts thus developed, will then be used in the following GLEPs to describe a comprehensive security solution for this distribution process that prevents trivial attacks and increases the difficulty on more complex attacks.


Since at mid-2002 (see endnote: "History of tree-signing in Gentoo"), many discussions have taken place on the gentoo-dev mailing list and in many other places to design and implement a security strategy for the distribution of files by the Gentoo project.

Usually the goal of such proposals was and is to be able to securely identify the data provided by Gentoo and prevent third parties (like a compromised mirror) from delivering harmful data (be it as modified ebuilds, executable shell code or any other form) to the users of the Gentoo MetaDistribution.

These strategies can neither prevent a malicious or compromised upstream from injecting "bad" programs, nor can they stop a rogue developer from committing malicious ebuilds. What they can do is to reduce the attack vectors so that for example a compromised mirror will be detected and no tainted data will be executed on user's systems.

Gentoo's software distribution system as it presently stands, contains a number of security shortcomings. The last discussion on the gentoo-dev mailing list [] contains a good overview of most of the issues. Summarized here:

  • Unverifiable executable code distributed: The most obvious instance are eclasses, but there are many other bits of the tree that are not signed at all right now. Modifying that data is trivial.
  • Shortcomings of existing Manifest verification A lack and enforcement of policies, combined with suboptimal support in portage, makes it trivial to modify or replace the existing Manifests.
  • Vulnerability of existing infrastructure to attacks. The previous two items make it possible for a skilled attacker to design an attack and then execute it against specific portions of existing infrastructure (e.g.: Compromise a country-local rsync mirror, and totally replace a package and its Manifest).


Security is not something that can be considered in isolation. It is both an ongoing holistic process and lessons learnt by examining previous shortcomings.

System Elements

There are a few entities to be considered:
  • Upstream. The people who provide the program(s) or data we wish to distribute.
  • Gentoo Developers. The people that package and test the things provided by Upstream.
  • Gentoo Infrastructure. The people and hardware that allow the revision control of metadata and distribution of the data and metadata provided by Developers and Upstream.
  • Gentoo Mirrors. Hardware provided by external contributors that is not or only marginally controlled by Gentoo Infrastructure. Needed to achieve the scalability and performance needed for the substantial Gentoo user base.
  • Gentoo Users. The people that use the Gentoo MetaDistribution.

The data described here is usually programs and data files provided by upstream; as this is a rather large amount of data it is usually distributed over http or ftp from Gentoo Mirrors. This data is usually labeled as "distfiles". Metadata is all information describing how to manipulate that data - it is usually called "The Tree" or "The Portage Tree", consists of many ebuilds, eclasses and supporting files and is usually distributed over rsync. The central rsync servers are controlled by Gentoo Infrastructure, but many third-party rsync mirrors exist that help to reduce the load on those central servers. These extra mirrors are not maintained by Gentoo Infrastructure.

Attacks may be conducted against any of these entities. Obviously direct attacks against Upstream and Users are outside of the scope of this series of GLEPs as they are not in any way controlled or controllable by Gentoo - however attacks using Gentoo as a conduit (including malicious mirrors) must be considered.


There are two major processes in the distribution of Gentoo, where security needs to be implemented:

  • Developer commits to version control systems controlled by Infrastructure.
  • Tree and distfile distribution from Infrastructure to Users, via the mirrors (this includes both HTTP and rsync distribution).

Both processes need their security improved. In [GLEPxx2] we will discuss how to improve the security of the first process. The relatively speaking simpler process of file distribution will be described in [GLEP58]. Since it can be implemented without having to change the workflow and behaviour of developers we hope to get it done in a reasonably short timeframe.

Attacks against Processes

Attacks against the process #1 may be as complex as a malicious or compromised developer (stolen SSH keys, rooted systems), or as simple as a patch from a user that does a little more than it claims, and is not adequately reviewed.

Attacks against the process #2 may be as simple as a single rooted mirror, distributing a modified tree to the users of that mirror - or some alteration of upstream sources. These attacks have a low cost and are very hard to discover unless all distributed data is transparently signed.

A simple example of such an attack and a partial solution for eclasses is presented in [ ]. It shows quite well that any non-Gentoo controlled rsync mirror can modify executable code; as much of this code is per default run as root a malicious mirror could compromise hundreds of systems per day - if cloaked well enough, such an attack could run for weeks before being noticed. As there are no effective safeguards right now users are left with the choice of either syncing from the sometimes slow or even unresponsive Gentoo-controlled rsync mirrors or risk being compromised by syncing from one of the community-provided mirrors. We will show that protection against this class of attacks is very easy to implement with little added cost.

At the level of mirrors, addition of malicious content is not the only attack. As discussed by Cappos et al [C08a,C08b], an attacker may use exclusion and replay attacks, possibly only on a specific subset of user to extend the window of opportunity on another exploit.

Security for Processes

Protection for process #1 can never be complete (without major modifications to our development process), as a malicious developer is fully authorized to provide materials for distribution. Partial protection can be gained by Portage and Infrastructure changes, but the real improvements needed are developer education and continued vigilance. This is further discussed in [GLEPxx2].

This security is still limited in scope - protection against compromised developers is very expensive, and even complex systems like peer review / multiple signatures can be broken by colluding developers. There are many issues, be it social or technical, that increase the cost of such measures a lot while only providing marginal security gains. Any implementation proposal must be carefully analysed to find the best security to developer hassle ratio.

Protection for process #2 is a different matter entirely. While it also cannot be complete (as the User may be attacked directly), we can ensure that Gentoo infrastructure and the mirrors are not a weak point. This objective is actually much closer than it seems already - most of the work has been completed for other things! This is further discussed in [GLEP58]. As this process has the most to gain in security, and the most immediate impact, it should be implemented before or at the same time as any changes to process #1. Security at this layer is already available in the signed daily snapshots, but we can extend it to cover the rsync mirrors as well.

Requirements pertaining to and management of keys (OpenPGP or otherwise) is an issue that affects both processes, and is broken out into a separate GLEP due to the technical complexity of the subject. This deals with everything including: types of keys to use; usage guidelines; procedures for managing signatures and trust for keys, including cases of lost (destroyed) and stolen (or otherwise turned malicious) keys.

Backwards Compatibility

As an informational GLEP, this document has no direct impact on backwards compatibility. However the related in-depth documents may delve further into any issues of backwards compatibility.

Endnote: History of tree-signing in Gentoo

This is a brief review of every previous tree-signing discussion, the stuff before 2003-04-03 was very hard to come by, so I apologize if I've missed a discussion (I would like to hear about it). I think there was a very early private discussion with drobbins in 2001, as it's vaguely referenced, but I can't find it anywhere.

2002-06-06, gentoo-dev mailing list, users first ask about signing of ebuilds: [ ]

2003-01-13, gentoo-dev mailing list, "Re: Verifying portage is from Gentoo" - Paul de Vrieze (pauldv): [ ]

2003-04, GWN articles announcing tree signing: [ ] [ ]

2003-04, gentoo-security mailing list, "The state of ebuild signing in portage" - Joshua Brindle (method), the first suggestion of signed Manifests, but also an unusual key-trust model: [ ]

2003-04, gentoo-core mailing list, "New Digests and Signing -- Attempted Explanation"

2003-06, gentoo-core mailing list, "A quick guide to GPG and key signing." - This overview was one of the first to help developers see how to use their devs, and was mainly intended for keysigning meetups.

2003-08-09, gentoo-core mailing list, "Ebuild signing" - status query, with an not very positive response, delayed by Nick Jones (carpaski) getting rooted and a safe cleanup taking a long time to affect.

2003-12-02, gentoo-core mailing list, "Report: compromised"

2003-12-03, gentoo-core mailing list, "Signing of ebuilds"

2003-12-07, gentoo-core mailing list, "gpg signing of Manifests", thread includes the first GnuPG signing prototype code, by Robin H. Johnson (robbat2). Andrew Cowie (rac) also produces a proof-of-concept around this time.

2004-03-23, gentoo-dev mailing list, "2004.1 will not include a secure portage" - Kurt Lieber (klieber). Signing is nowhere near ready for 2004.1 release, and it is realized that it there is insufficient traction and the problem is very large. Many arguments about the checking and verification side. First warning signs that MD5 might be broken in the near future. [ ]

2004-03-25, gentoo-dev mailing list, "Redux: 2004.1 will not include a secure portage" - Robin H. Johnson (robbat2). Yet another proposal, summarizing the points of the previous thread and this time trying to track the various weaknesses.

2004-05-31, Gentoo managers meeting, portage team reports that FEATURES=sign is now available, but large questions still exist over verification policies and procedures, as well as handing of keys. [ ]

2005-01-17, gentoo-core mailing list, "Global objective for 2005 : portage signing". Thierry Carrez (koon) suggests that more go into tree-signing work. Problems at the time later in the thread show that the upstream gpg-agent is not ready, amongst other minor implementation issues.

2005-02-20, gentoo-dev mailing list, "post-LWE 2005" - Brian Harring (ferringb). A discussion on the ongoing lack of signing, and that eclasses and profiles need to be signed as well, but this seems to be hanging on GLEP33 in the meantime. [ ]

2005-03-08, gentoo-core mailing list, "gpg manifest signing stats". Informal statistics show that 26% of packages in the tree include a signed Manifest. Questions are raised regarding key types, and key policies.

2005-11-16, gentoo-core mailing list, "Gentoo key signing practices and official Gentoo keyring". A discussion of key handling and other outstanding issues, also mentioning partial Manifests, as well as a comparision between the signing procedures used in Slackware, Debian and RPM-based distros.

2005-11-19, gentoo-portage-dev mailing list, "Manifest signing" - Robin H. Johnson (robbat2) follows up the previous -core posting, discussion implementation issues. [ ]

2006-05-18, gentoo-dev mailing list, "Signing everything, for fun and for profit" - Patrick Lauer (bonsaikitten). Later brings up that Manifest2 is needed for getting everything right. [ ]

2006-05-19, gentoo-dev mailing list, "Re: Signing everything, for fun and for profit" - Robin H. Johnson (robbat2). An introduction into some of the OpenPGP standard, with a focus on how it affects file signing, key signing, management of keys, and revocation. [ ]

2007-04-11, gentoo-dev mailing list, "Re: DEVELOPMENT mail list, right?" - Robin H. Johnson (robbat2). A progress report on these very GLEPs. [ ]

2007-07-02, gentoo-dev mailing list, "Re: Re: Nominations open for the Gentoo Council 2007/08" - Robin H. Johnson (robbat2). Another progress report. [ ]

2007-11-30, portage-dev alias, "Manifest2 and Tree-signing" - Robin H. Johnson (robbat2). First review thread for these GLEPs, many suggestions from Marius Mauch (genone).

2008-04-03, gentoo-dev mailing list, "Re: Monthly Gentoo Council Reminder for April" - Ciaran McCreesh (ciaranm). A thread in which Ciaran reminds everybody that simply making all the developers sign the tree is not sufficient to prevent all attacks. [ ]

2008-07-01, gentoo-portage-dev mailing list, "proto-GLEPS for Tree-signing" - Robin H. Johnson (robbat2). Thread looking for review input from Portage developers. [ ]

2008-07-12, gentoo-portage-dev mailing list, "proto-GLEPS for Tree-signing, take 2" - Robin H. Johnson (robbat2). Integration of changes from previous review, and a prototype for the signing code. zmedico also posts a patch for a verification prototype. [ ]


I'd like to thank Patrick Lauer (bonsaikitten) for prodding me to keep working on the tree-signing project, as well helping with spelling, grammar, research (esp. tracking down every possible vulnerability that has been mentioned in past discussions, and integrating them in this overview).


[C08a]Cappos, J et al. (2008). "Package Management Security". University of Arizona Technical Report TR08-02. Available online from:
[C08b]Cappos, J et al. (2008). "Attacks on Package Managers" Available online at:
[GLEP58]Security of distribution of Gentoo software - Infrastructure to User distribution - MetaManifest
[GLEPxx2]Future GLEP on Developer Process security.
[GLEPxx3]Future GLEP on GnuPG Policies and Handling.