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Document signing key management 

Add key management process sections with configuration details, a
transcript of key generation and an example of key signing.

Change-Id: Ibf4588437a9ed62c111df1728722358f51b92016
This commit is contained in:
Jeremy Stanley 2016-07-07 21:44:23 +00:00
parent 4c4b4449d3
commit d0b84c5b59
1 changed files with 436 additions and 4 deletions
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doc/source/signing.rst
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@ -80,8 +80,440 @@ completely, the revocation certificate generated at key creation
time should be used as a last resort.
Management
==========
Key Management Process
======================
As process is solidified, this section will be updated with specific
commands and examples.
Configuration
-------------
This is the content of the ``/root/signing.gnupg/gpg.conf`` file on
our management bastion host::
# A basic gpg.conf using secure keyserver transport and some more
# verbose display options. This configuration assumes you have
# installed both the gnupg and gnupg-curl packages. Set your umask
# to 077, create a /root/signing.gnupg directory and place this
# configuration file in it.
#
# Retrieve and validate the HKPS key for the SKS keyservers this way:
#
# wget -P ~/signing.gnupg/ \
# https://sks-keyservers.net/sks-keyservers.netCA.pem{,.asc}
# gpg --homedir signing.gnupg --recv-key \
# 0x94CBAFDD30345109561835AA0B7F8B60E3EDFAE3
# gpg --homedir signing.gnupg --verify \
# ~/signing.gnupg/sks-keyservers.netCA.pem{.asc,}
# Receive, send and search for keys in the SKS keyservers pool using
# HKPS (OpenPGP HTTP Keyserver Protocol via TLS/SSL).
keyserver hkps://hkps.pool.sks-keyservers.net
# Set the path to the public certificate for the
# sks-keyservers.net CA used to verify connections to servers in
# the pool above.
keyserver-options ca-cert-file=/root/signing.gnupg/sks-keyservers.netCA.pem
# Ignore keyserver URLs specified in retrieved/refreshed keys
# so they don't direct you to update from non-HKPS sources.
keyserver-options no-honor-keyserver-url
# Display key IDs in a more accurate 16-digit hexidecimal format
# and add 0x at the beginning for clarity.
keyid-format 0xlong
# Display the calculated validity of user IDs when listing keys or
# showing signatures.
list-options show-uid-validity
verify-options show-uid-validity
Generation
----------
Key generation should happen reasonably far in advance of expiration
of the old key (at least a month), so as to provide ample time for a
majority of our root sysadmins to attest to the key and provide
warning to the rest of the community of the upcoming transition. Of
course, if this is being done to replace a revoked key, this
timeline should be accelerated as much as possible to provide
continuity of service so use your best judgement on a balance of
sufficient attestation and warning (same-day turnaround is
preferred).
Make sure we start with a restrictive umask so that files and
directories we write from this point forward are only accessible by
the root user:
.. code-block:: shell-session
root@puppetmaster:~# umask 077
Now create a master key for the coming development cycle, taking
mostly the GnuPG recommended default values. Set a validity period
sufficient to last through the release process at the conclusion of
the cycle. Use a sufficiently long, randomly-generated passphrase
string (it's fine to reuse the one stored in our passwords list for
earlier keys unless we know it to have been compromised):
.. code-block:: shell-session
root@puppetmaster:~# gpg --homedir signing.gnupg --gen-key
gpg (GnuPG) 1.4.16; Copyright (C) 2013 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
Please select what kind of key you want:
(1) RSA and RSA (default)
(2) DSA and Elgamal
(3) DSA (sign only)
(4) RSA (sign only)
Your selection?
RSA keys may be between 1024 and 4096 bits long.
What keysize do you want? (2048)
Requested keysize is 2048 bits
Please specify how long the key should be valid.
0 = key does not expire
<n> = key expires in n days
<n>w = key expires in n weeks
<n>m = key expires in n months
<n>y = key expires in n years
Key is valid for? (0) 7m
Key expires at Thu 02 Feb 2017 08:41:39 PM UTC
Is this correct? (y/N) y
You need a user ID to identify your key; the software constructs the user ID
from the Real Name, Comment and Email Address in this form:
"Heinrich Heine (Der Dichter) <heinrichh@duesseldorf.de>"
Real name: OpenStack Infra
Email address: infra-root@openstack.org
Comment: Some Cycle
You selected this USER-ID:
"OpenStack Infra (Some Cycle) <infra-root@openstack.org>"
Change (N)ame, (C)omment, (E)mail or (O)kay/(Q)uit? o
You need a Passphrase to protect your secret key.
Enter passphrase: ********************************
Repeat passphrase: ********************************
We need to generate a lot of random bytes. It is a good idea to perform
some other action (type on the keyboard, move the mouse, utilize the
disks) during the prime generation; this gives the random number
generator a better chance to gain enough entropy.
.+++++
......+++++
We need to generate a lot of random bytes. It is a good idea to perform
some other action (type on the keyboard, move the mouse, utilize the
disks) during the prime generation; this gives the random number
generator a better chance to gain enough entropy.
.+++++
+++++
gpg: key 0x120D3C23C6D5584D marked as ultimately trusted
public and secret key created and signed.
gpg: checking the trustdb
gpg: 3 marginal(s) needed, 1 complete(s) needed, PGP trust model
gpg: depth: 0 valid: 1 signed: 0 trust: 0-, 0q, 0n, 0m, 0f, 1u
gpg: next trustdb check due at 2017-02-02
pub 2048R/0x120D3C23C6D5584D 2016-07-07 [expires: 2017-02-02]
Key fingerprint = 7222 E5A0 5730 B767 0F93 035A 120D 3C23 C6D5 584D
uid [ultimate] OpenStack Infra (Some Cycle) <infra-root@openstack.org>
sub 2048R/0x1F215B56867C5D9A 2016-07-07 [expires: 2017-02-02]
Create a revocation certificate for the master key, for use in the
case extreme case that this master key itself becomes inaccessible,
for example because the decryption passphrase is lost (under any
other circumstances, a revocation certificate with a more detailed
description can be generated using the master key on an as-needed
basis):
.. code-block:: shell-session
root@puppetmaster:~# gpg --homedir signing.gnupg --output \
> signing.gnupg/revoke.asc --gen-revoke 0x120D3C23C6D5584D
sec 2048R/0x120D3C23C6D5584D 2016-07-07 OpenStack Infra (Some Cycle) <infra-root@openstack.org>
Create a revocation certificate for this key? (y/N) y
Please select the reason for the revocation:
0 = No reason specified
1 = Key has been compromised
2 = Key is superseded
3 = Key is no longer used
Q = Cancel
(Probably you want to select 1 here)
Your decision? 1
Enter an optional description; end it with an empty line:
> This revocation is to be used in the event the key cannot be recovered.
>
Reason for revocation: Key has been compromised
This revocation is to be used in the event the key cannot be recovered.
Is this okay? (y/N) y
You need a passphrase to unlock the secret key for
user: "OpenStack Infra (Some Cycle) <infra-root@openstack.org>"
2048-bit RSA key, ID 0x120D3C23C6D5584D, created 2016-07-07
Enter passphrase: ********************************
ASCII armored output forced.
Revocation certificate created.
Please move it to a medium which you can hide away; if Mallory gets
access to this certificate he can use it to make your key unusable.
It is smart to print this certificate and store it away, just in case
your media become unreadable. But have some caution: The print system of
your machine might store the data and make it available to others!
Use the interactive key editor to add a subkey constrained to
signing purposes only. It does not need an expiration since it will
be valid only for as long as its associated master key is valid:
.. code-block:: shell-session
root@puppetmaster:~# gpg --homedir signing.gnupg --edit-key 0x120D3C23C6D5584D
gpg (GnuPG) 1.4.16; Copyright (C) 2013 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
Secret key is available.
pub 2048R/0x120D3C23C6D5584D created: 2016-07-07 expires: 2017-02-02 usage: SC
trust: ultimate validity: ultimate
sub 2048R/0x1F215B56867C5D9A created: 2016-07-07 expires: 2017-02-02 usage: E
[ultimate] (1). OpenStack Infra (Some Cycle) <infra-root@openstack.org>
gpg> addkey
Key is protected.
You need a passphrase to unlock the secret key for
user: "OpenStack Infra (Some Cycle) <infra-root@openstack.org>"
2048-bit RSA key, ID 0x120D3C23C6D5584D, created 2016-07-07
Enter passphrase: ********************************
Please select what kind of key you want:
(3) DSA (sign only)
(4) RSA (sign only)
(5) Elgamal (encrypt only)
(6) RSA (encrypt only)
Your selection? 4
RSA keys may be between 1024 and 4096 bits long.
What keysize do you want? (2048)
Requested keysize is 2048 bits
Please specify how long the key should be valid.
0 = key does not expire
<n> = key expires in n days
<n>w = key expires in n weeks
<n>m = key expires in n months
<n>y = key expires in n years
Key is valid for? (0)
Key does not expire at all
Is this correct? (y/N) y
Really create? (y/N) y
We need to generate a lot of random bytes. It is a good idea to perform
some other action (type on the keyboard, move the mouse, utilize the
disks) during the prime generation; this gives the random number
generator a better chance to gain enough entropy.
+++++
........+++++
pub 2048R/0x120D3C23C6D5584D created: 2016-07-07 expires: 2017-02-02 usage: SC
trust: ultimate validity: ultimate
sub 2048R/0x1F215B56867C5D9A created: 2016-07-07 expires: 2017-02-02 usage: E
sub 2048R/0xC0224DB5F541FB68 created: 2016-07-07 expires: never usage: S
[ultimate] (1). OpenStack Infra (Some Cycle) <infra-root@openstack.org>
gpg> save
Now send the master key to the keyserver network. The subkeys are
all submitted along with it, so do not need to be specified
separately:
.. code-block:: shell-session
root@puppetmaster:~# gpg --homedir signing.gnupg --send-keys 0x120D3C23C6D5584D
sending key 0x120D3C23C6D5584D to hkps server hkps.pool.sks-keyservers.net
The rest of this process shouldn't happen until we're ready for the
signing system to transition to our new key. In a typical,
non-emergency rotation this should not happen until release
activities for the previous cycle have concluded so that we don't
inadvertently sign their artifacts with the new key.
Create a new GnuPG keychain by exporting a copy of just the signing
subkey to a file and then importing that (and only that) in a new
GnuPG directory:
.. code-block:: shell-session
root@puppetmaster:~# mkdir temporary.gnupg
root@puppetmaster:~# gpg --homedir signing.gnupg --output \
> temporary.gnupg/secret-subkeys --export-secret-subkeys 0xC0224DB5F541FB68\!
root@puppetmaster:~# gpg --homedir temporary.gnupg --import \
> temporary.gnupg/secret-subkeys
gpg: keyring `temporary.gnupg/secring.gpg' created
gpg: keyring `temporary.gnupg/pubring.gpg' created
gpg: key C6D5584D: secret key imported
gpg: temporary.gnupg/trustdb.gpg: trustdb created
gpg: key C6D5584D: public key "OpenStack Infra (Some Cycle) <infra-root@openstack.org>" imported
gpg: Total number processed: 1
gpg: imported: 1 (RSA: 1)
gpg: secret keys read: 1
gpg: secret keys imported: 1
So that our CI jobs will be able to make use of this subkey without
interactively supplying a passphrase, the old passphrase (exported
from the master key) must be reset to an empty string in the new
temporary copy. This is again done using an interactive key editor
session:
.. code-block:: shell-session
root@puppetmaster:~# gpg --homedir temporary.gnupg --edit-key 0xC0224DB5F541FB68
gpg (GnuPG) 1.4.16; Copyright (C) 2013 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
Secret key is available.
pub 2048R/C6D5584D created: 2016-07-07 expires: 2017-02-02 usage: SC
trust: unknown validity: unknown
sub 2048R/F541FB68 created: 2016-07-07 expires: never usage: S
[ unknown] (1). OpenStack Infra (Some Cycle) <infra-root@openstack.org>
gpg> passwd
Secret parts of primary key are not available.
You need a passphrase to unlock the secret key for
user: "OpenStack Infra (Some Cycle) <infra-root@openstack.org>"
2048-bit RSA key, ID F541FB68, created 2016-07-07
Enter passphrase: ********************************
Enter the new passphrase for this secret key.
Enter passphrase:
Repeat passphrase:
You don't want a passphrase - this is probably a *bad* idea!
Do you really want to do this? (y/N) y
gpg> save
This leaves us with a temporary keyring containing only an
unencrypted copy of the signing subkey. Push this into private hiera
so that it will be installed onto the signing system by our
configuration management:
.. code-block:: shell-session
root@puppetmaster:~# /opt/system-config/production/tools/hieraedit.py --yaml \
> /opt/system-config/hieradata/production/group/signing.yaml -f \
> temporary.gnupg/pubring.gpg pubring
root@puppetmaster:~# /opt/system-config/production/tools/hieraedit.py --yaml \
> /opt/system-config/hieradata/production/group/signing.yaml -f \
> temporary.gnupg/secring.gpg secring
Finally, do your best to securely remove the temporary copy of the
unencrypted signing subkey and any associated files:
.. code-block:: shell-session
root@puppetmaster:~# shred temporary.gnupg/*
root@puppetmaster:~# rm -rf temporary.gnupg
Attestation
-----------
We need a majority (if not all) of our current root sysadmins to
verify and attest to the authenticity of our artifact signing key,
because it represents a system maintained by our team rather than
representing some particular individual and so anyone else attesting
to this key can really only do so transitively through us. This
should be done soon after a new key is minted (preferably the same
week) so that others in the community who wish to extend the web of
trust around the key based on our attestations (for example, release
managers or team leads) have an opportunity to do so before it's put
into production.
Start by logging into the management bastion and examining the
fingerprint of the key as it exists on disk:
.. code-block:: shell-session
me@puppetmaster:~$ sudo gpg --homedir /root/signing.gnupg --fingerprint \
> --list-keys "OpenStack Infra (Some Cycle)"
pub 2048R/0x120D3C23C6D5584D 2016-07-07 [expires: 2017-02-02]
Key fingerprint = 120D 3C23 C6D5 584D 6FC2 4646 64DB B05A CC5E 7C28
uid [ultimate] OpenStack Infra (Some Cycle) <infra-root@openstack.org>
sub 2048R/0x1F215B56867C5D9A 2016-07-07 [expires: 2017-02-02]
sub 2048R/0xC0224DB5F541FB68 2016-07-07
Now on your own system where your OpenPGP key resides, retrieve the
key, compare the fingerprint from above, and if they match, sign it
and push the signature back to the keyserver network:
.. code-block:: shell-session
me@home:~$ gpg2 --recv-keys 0x120D3C23C6D5584D
gpg: requesting key 0x120D3C23C6D5584D from hkps server hkps.pool.sks-keyservers.net
gpg: key 0x120D3C23C6D5584D: public key "OpenStack Infra (Some Cycle) <infra-root@openstack.org>" imported
gpg: 3 marginal(s) needed, 1 complete(s) needed, classic trust model
gpg: depth: 0 valid: 3 signed: 31 trust: 0-, 0q, 0n, 0m, 0f, 3u
gpg: depth: 1 valid: 31 signed: 46 trust: 30-, 0q, 0n, 0m, 1f, 0u
gpg: next trustdb check due at 2016-11-30
gpg: Total number processed: 1
gpg: imported: 1 (RSA: 1)
me@home:~$ gpg2 --fingerprint 0x120D3C23C6D5584D
pub 2048R/0x120D3C23C6D5584D 2016-07-07 [expires: 2017-02-02]
Key fingerprint = 120D 3C23 C6D5 584D 6FC2 4646 64DB B05A CC5E 7C28
uid [ full ] OpenStack Infra (Some Cycle) <infra-root@openstack.org>
sub 2048R/0x1F215B56867C5D9A 2016-07-07 [expires: 2017-02-02]
sub 2048R/0xC0224DB5F541FB68 2016-07-07
me@home:~$ gpg2 --sign-key 0x120D3C23C6D5584D
pub 2048R/0x120D3C23C6D5584D created: 2016-07-07 expires: 2017-02-02 usage: SC
trust: unknown validity: full
sub 2048R/0x1F215B56867C5D9A created: 2016-07-07 expires: 2017-02-02 usage: E
sub 2048R/0xC0224DB5F541FB68 created: 2016-07-07 expires: never usage: S
[ full ] (1). OpenStack Infra (Some Cycle) <infra-root@openstack.org>
pub 2048R/0x120D3C23C6D5584D created: 2016-07-07 expires: 2017-02-02 usage: SC
trust: unknown validity: full
Primary key fingerprint: 120D 3C23 C6D5 584D 6FC2 4646 64DB B05A CC5E 7C28
OpenStack Infra (Some Cycle) <infra-root@openstack.org>
This key is due to expire on 2017-02-02.
Are you sure that you want to sign this key with your
key "My Name <me@example.org>" (0xAB54A98CEB1F0AD2)
Really sign? (y/N) y
+-----------------------------------------------------------------------+
| Please enter the passphrase to unlock the secret key for the OpenPGP |
| certificate: |
| "My Name <me@example.org>" |
| 2048-bit RSA key, ID 0xAB54A98CEB1F0AD2, |
| created 2008-09-10. |
| |
| |
| Passphrase **********************____________________________________ |
| |
| <OK> <Cancel> |
+-----------------------------------------------------------------------+
me@home:~$ gpg2 --send-keys 0x120D3C23C6D5584D
gpg: sending key 0x120D3C23C6D5584D to hkps server hkps.pool.sks-keyservers.net
Also, please retrieve a copy of the
``/root/signing.gnupg/revoke.asc`` fallback revocation certificate
from the management bastion and keep it stashed somewhere secure,
for emergency use in the (hopefully very unlikely) event that our
OpenPGP master private key is completely lost to us (for example, if
we lose the file containing its decryption passphrase and all
backups thereof).