Let’s reflect on some of my recent work that started with understanding Trisquel GNU/Linux, improving transparency into apt-archives, working on reproducible builds of Trisquel, strengthening verification of apt-archives with Sigstore, and finally thinking about security device threat models. A theme in all this is improving methods to have trust in machines, or generally any external entity. While I believe that everything starts by trusting something, usually something familiar and well-known, we need to deal with misuse of that trust that leads to failure to deliver what is desired and expected from the trusted entity. How can an entity behave to invite trust? Let’s argue for some properties that can be quantitatively measured, with a focus on computer software and hardware:
Deterministic Behavior – given a set of circumstances, it should behave the same.
Verifiability and Transparency – the method (the source code) should be accessible for understanding (compare scientific method) and its binaries verifiable, i.e., it should be possible to verify that the entity actually follows the intended deterministic method (implying efforts like reproducible builds and bootstrappable builds).
Accountable – the entity should behave the same for everyone, and deviation should be possible prove in a way that is hard to deny, implying efforts such as Certificate Transparency and more generic checksum logs like Sigstore and Sigsum.
Liberating – the tools and documentation should be available as free software to enable you to replace the trusted entity if so desired. An entity that wants to restrict you from being able to replace the trusted entity is vulnerable to corruption and may stop acting trustworthy. This point of view reinforces that open source misses the point; it has become too common to use trademark laws to restrict re-use of open source software (e.g., firefox, chrome, rust).
Essentially, this boils down to: Trust, Verify and Hold Accountable. To put this dogma in perspective, it helps to understand that this approach may be harmful to human relationships (which could explain the social awkwardness of hackers), but it remains useful as a method to improve the design of computer systems, and a useful method to evaluate safety of computer systems. When a system fails some of the criteria above, we know we have more work to do to improve it.
How far have we come on this journey? Through earlier efforts, we are in a fairly good situation. Richard Stallman through GNU/FSF made us aware of the importance of free software, the Reproducible/Bootstrappable build projects made us aware of the importance of verifiability, and Certificate Transparency highlighted the need for accountable signature logs leading to efforts like Sigstore for software. None of these efforts would have seen the light of day unless people wrote free software and packaged them into distributions that we can use, and built hardware that we can run it on. While there certainly exists more work to be done on the software side, with the recent amazing full-source build of Guix based on a 357-byte hand-written seed, I believe that we are closing that loop on the software engineering side.
So what remains? Some inspiration for further work:
Accountable binary software distribution remains unresolved in practice, although we have some software components around (e.g., apt-sigstore and guix git authenticate). What is missing is using them for verification by default and/or to improve the signature process to use trustworthy hardware devices, and committing the signatures to transparency logs.
Trustworthy hardware to run trustworthy software on remains a challenge, and we owe FSF’s Respect Your Freedom credit for raising awareness of this. Many modern devices requires non-free software to work which fails most of the criteria above and are thus inherently untrustworthy.
Verifying rebuilds of currently published binaries on trustworthy hardware is unresolved.
Completing a full-source rebuild from a small seed on trustworthy hardware remains, preferably on a platform wildly different than X86 such as Raptor’s Talos II.
We need improved security hardware devices and improved established practices on how to use them. For example, while Gnuk on the FST enable a trustworthy software and hardware solution, the best process for using it that I can think of generate the cryptographic keys on a more complex device. Efforts like Tillitis are inspiring here.
Onwards and upwards, happy hacking!
Update 2023-05-03: Added the “Liberating” property regarding free software, instead of having it be part of the “Verifiability and Transparency”.
I’ve used hardware-backed OpenPGP keys since 2006 when I imported newly generated rsa1024 subkeys to a FSFE Fellowship card. This worked well for several years, and I recall buying more ZeitControl cards for multi-machine usage and backup purposes. As a side note, I recall being unsatisfied with the weak 1024-bit RSA subkeys at the time – my primary key was a somewhat stronger 1280-bit RSA key created back in 2002 — but OpenPGP cards at the time didn’t support more than 1024 bit RSA, and were (and still often are) also limited to power-of-two RSA key sizes which I dislike.
I had my master key on disk with a strong password for a while, mostly to refresh expiration time of the subkeys and to sign other’s OpenPGP keys. At some point I stopped carrying around encrypted copies of my master key. That was my main setup when I migrated to a new stronger RSA 3744 bit key with rsa2048 subkeys on a YubiKey NEO back in 2014. At that point, signing other’s OpenPGP keys was a rare enough occurrence that I settled with bringing out my offline machine to perform this operation, transferring the public key to sign on USB sticks. In 2019 I re-evaluated my OpenPGP setup and ended up creating a offline Ed25519 key with subkeys on a FST-01G running Gnuk. My approach for signing other’s OpenPGP keys were still to bring out my offline machine and sign things using the master secret using USB sticks for storage and transport. Which meant I almost never did that, because it took too much effort. So my 2019-era Ed25519 key still only has a handful of signatures on it, since I had essentially stopped signing other’s keys which is the traditional way of getting signatures in return.
None of this caused any critical problem for me because I continued to use my old 2014-era RSA3744 key in parallel with my new 2019-era Ed25519 key, since too many systems didn’t handle Ed25519. However, during 2022 this changed, and the only remaining environment that I still used my RSA3744 key for was in Debian — and they require OpenPGP signatures on the new key to allow it to replace an older key. I was in denial about this sub-optimal solution during 2022 and endured its practical consequences, having to use the YubiKey NEO (which I had replaced with a permanently inserted YubiKey Nano at some point) for Debian-related purposes alone.
In December 2022 I bought a new laptop and setup a FST-01SZ with my Ed25519 key, and while I have taken a vacation from Debian, I continue to extend the expiration period on the old RSA3744-key in case I will ever have to use it again, so the overall OpenPGP setup was still sub-optimal. Having two valid OpenPGP keys at the same time causes people to use both for email encryption (leading me to have to use both devices), and the WKD Key Discovery protocol doesn’t like two valid keys either. At FOSDEM’23 I ran into Andre Heinecke at GnuPG and I couldn’t help complain about how complex and unsatisfying all OpenPGP-related matters were, and he mildly ignored my rant and asked why I didn’t put the master key on another smartcard. The comment sunk in when I came home, and recently I connected all the dots and this post is a summary of what I did to move my offline OpenPGP master key to a Nitrokey Start.
First a word about device choice, I still prefer to use hardware devices that are as compatible with free software as possible, but the FST-01G or FST-01SZ are no longer easily available for purchase. I got a comment about Nitrokey start in my last post, and had two of them available to experiment with. There are things to dislike with the Nitrokey Start compared to the YubiKey (e.g., relative insecure chip architecture, the bulkier form factor and lack of FIDO/U2F/OATH support) but – as far as I know – there is no more widely available owner-controlled device that is manufactured for an intended purpose of implementing an OpenPGP card. Thus it hits the sweet spot for me.
Nitrokey Start
The first step is to run latest firmware on the Nitrokey Start – for bug-fixes and important OpenSSH 9.0 compatibility – and there are reproducible-built firmware published that you can install using pynitrokey. I run Trisquel 11 aramo on my laptop, which does not include the Python Pip package (likely because it promotes installing non-free software) so that was a slight complication. Building the firmware locally may have worked, and I would like to do that eventually to confirm the published firmware, however to save time I settled with installing the Ubuntu 22.04 packages on my machine:
$ sha256sum python3-pip*
ded6b3867a4a4cbaff0940cab366975d6aeecc76b9f2d2efa3deceb062668b1c python3-pip_22.0.2+dfsg-1ubuntu0.2_all.deb
e1561575130c41dc3309023a345de337e84b4b04c21c74db57f599e267114325 python3-pip-whl_22.0.2+dfsg-1ubuntu0.2_all.deb
$ doas dpkg -i python3-pip*
...
$ doas apt install -f
...
$
Installing pynitrokey downloaded a bunch of dependencies, and it would be nice to audit the license and security vulnerabilities for each of them. (Verbose output below slightly redacted.)
jas@kaka:~$ pip3 install --user pynitrokey
Collecting pynitrokey
Downloading pynitrokey-0.4.34-py3-none-any.whl (572 kB)
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Downloading pyocd_pemicro-1.1.5-py3-none-any.whl (9.0 kB)
Requirement already satisfied: colorama<1,>=0.4.4 in /usr/lib/python3/dist-packages (from spsdk<1.8.0,>=1.7.0->pynitrokey) (0.4.4)
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Requirement already satisfied: bitstring<3.2,>=3.1 in /usr/lib/python3/dist-packages (from spsdk<1.8.0,>=1.7.0->pynitrokey) (3.1.7)
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Downloading fire-0.5.0.tar.gz (88 kB)
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Requirement already satisfied: appdirs>=1.4 in /usr/lib/python3/dist-packages (from cmsis-pack-manager<0.3.0->spsdk<1.8.0,>=1.7.0->pynitrokey) (1.4.4)
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Downloading lark-parser-0.7.8.tar.gz (276 kB)
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Requirement already satisfied: MarkupSafe>=2.0 in /usr/lib/python3/dist-packages (from jinja2<3.1,>=2.11->spsdk<1.8.0,>=1.7.0->pynitrokey) (2.0.1)
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Downloading wrapt-1.15.0-cp310-cp310-manylinux_2_5_x86_64.manylinux1_x86_64.manylinux_2_17_x86_64.manylinux2014_x86_64.whl (78 kB)
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Collecting psutil>=5.2.2
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Building wheels for collected packages: nrfutil, crcmod, sly, tlv8, commentjson, hexdump, pyspinel, fire, intervaltree, lark-parser, naturalsort, future
Building wheel for nrfutil (setup.py) ... done
Created wheel for nrfutil: filename=nrfutil-6.1.7-py3-none-any.whl size=898520 sha256=de6f8803f51d6c26d24dc7df6292064a468ff3f389d73370433fde5582b84a10
Stored in directory: /home/jas/.cache/pip/wheels/39/2b/9b/98ab2dd716da746290e6728bdb557b14c1c9a54cb9ed86e13b
Building wheel for crcmod (setup.py) ... done
Created wheel for crcmod: filename=crcmod-1.7-cp310-cp310-linux_x86_64.whl size=31422 sha256=5149ac56fcbfa0606760eef5220fcedc66be560adf68cf38c604af3ad0e4a8b0
Stored in directory: /home/jas/.cache/pip/wheels/85/4c/07/72215c529bd59d67e3dac29711d7aba1b692f543c808ba9e86
Building wheel for sly (setup.py) ... done
Created wheel for sly: filename=sly-0.4-py3-none-any.whl size=27352 sha256=f614e413918de45c73d1e9a8dca61ca07dc760d9740553400efc234c891f7fde
Stored in directory: /home/jas/.cache/pip/wheels/a2/23/4a/6a84282a0d2c29f003012dc565b3126e427972e8b8157ea51f
Building wheel for tlv8 (setup.py) ... done
Created wheel for tlv8: filename=tlv8-0.10.0-py3-none-any.whl size=11266 sha256=3ec8b3c45977a3addbc66b7b99e1d81b146607c3a269502b9b5651900a0e2d08
Stored in directory: /home/jas/.cache/pip/wheels/e9/35/86/66a473cc2abb0c7f21ed39c30a3b2219b16bd2cdb4b33cfc2c
Building wheel for commentjson (setup.py) ... done
Created wheel for commentjson: filename=commentjson-0.9.0-py3-none-any.whl size=12092 sha256=28b6413132d6d7798a18cf8c76885dc69f676ea763ffcb08775a3c2c43444f4a
Stored in directory: /home/jas/.cache/pip/wheels/7d/90/23/6358a234ca5b4ec0866d447079b97fedf9883387d1d7d074e5
Building wheel for hexdump (setup.py) ... done
Created wheel for hexdump: filename=hexdump-3.3-py3-none-any.whl size=8913 sha256=79dfadd42edbc9acaeac1987464f2df4053784fff18b96408c1309b74fd09f50
Stored in directory: /home/jas/.cache/pip/wheels/26/28/f7/f47d7ecd9ae44c4457e72c8bb617ef18ab332ee2b2a1047e87
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Created wheel for pyspinel: filename=pyspinel-1.0.3-py3-none-any.whl size=65033 sha256=01dc27f81f28b4830a0cf2336dc737ef309a1287fcf33f57a8a4c5bed3b5f0a6
Stored in directory: /home/jas/.cache/pip/wheels/95/ec/4b/6e3e2ee18e7292d26a65659f75d07411a6e69158bb05507590
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Created wheel for fire: filename=fire-0.5.0-py2.py3-none-any.whl size=116951 sha256=3d288585478c91a6914629eb739ea789828eb2d0267febc7c5390cb24ba153e8
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Created wheel for intervaltree: filename=intervaltree-3.1.0-py2.py3-none-any.whl size=26119 sha256=5ff1def22ba883af25c90d90ef7c6518496fcd47dd2cbc53a57ec04cd60dc21d
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Created wheel for lark-parser: filename=lark_parser-0.7.8-py2.py3-none-any.whl size=62527 sha256=3d2ec1d0f926fc2688d40777f7ef93c9986f874169132b1af590b6afc038f4be
Stored in directory: /home/jas/.cache/pip/wheels/29/30/94/33e8b58318aa05cb1842b365843036e0280af5983abb966b83
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Created wheel for naturalsort: filename=naturalsort-1.5.1-py3-none-any.whl size=7526 sha256=bdecac4a49f2416924548cae6c124c85d5333e9e61c563232678ed182969d453
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Created wheel for future: filename=future-0.18.3-py3-none-any.whl size=492037 sha256=57a01e68feca2b5563f5f624141267f399082d2f05f55886f71b5d6e6cf2b02c
Stored in directory: /home/jas/.cache/pip/wheels/5e/a9/47/f118e66afd12240e4662752cc22cefae5d97275623aa8ef57d
Successfully built nrfutil crcmod sly tlv8 commentjson hexdump pyspinel fire intervaltree lark-parser naturalsort future
Installing collected packages: tlv8, sortedcontainers, sly, pyserial, pyelftools, piccata, naturalsort, libusb1, lark-parser, intelhex, hexdump, fastjsonschema, crcmod, asn1crypto, wrapt, urllib3, typing_extensions, tqdm, termcolor, ruamel.yaml.clib, python-dateutil, pyspinel, pypemicro, pycryptodome, psutil, protobuf, prettytable, oscrypto, milksnake, libusbsio, jinja2, intervaltree, humanfriendly, future, frozendict, fido2, ecdsa, deepmerge, commentjson, click-option-group, click-command-tree, capstone, astunparse, argparse-addons, ruamel.yaml, pyocd-pemicro, pylink-square, pc_ble_driver_py, fire, cmsis-pack-manager, bincopy, pyocd, nrfutil, nkdfu, spsdk, pynitrokey
WARNING: The script nitropy is installed in '/home/jas/.local/bin' which is not on PATH.
Consider adding this directory to PATH or, if you prefer to suppress this warning, use --no-warn-script-location.
Successfully installed argparse-addons-0.12.0 asn1crypto-1.5.1 astunparse-1.6.3 bincopy-17.10.3 capstone-4.0.2 click-command-tree-1.1.0 click-option-group-0.5.5 cmsis-pack-manager-0.2.10 commentjson-0.9.0 crcmod-1.7 deepmerge-0.3.0 ecdsa-0.18.0 fastjsonschema-2.16.3 fido2-1.1.0 fire-0.5.0 frozendict-2.3.5 future-0.18.3 hexdump-3.3 humanfriendly-10.0 intelhex-2.3.0 intervaltree-3.1.0 jinja2-3.0.3 lark-parser-0.7.8 libusb1-1.9.3 libusbsio-2.1.11 milksnake-0.1.5 naturalsort-1.5.1 nkdfu-0.2 nrfutil-6.1.7 oscrypto-1.3.0 pc_ble_driver_py-0.17.0 piccata-2.0.3 prettytable-2.5.0 protobuf-3.20.3 psutil-5.9.4 pycryptodome-3.17 pyelftools-0.29 pylink-square-0.11.1 pynitrokey-0.4.34 pyocd-0.31.0 pyocd-pemicro-1.1.5 pypemicro-0.1.11 pyserial-3.5 pyspinel-1.0.3 python-dateutil-2.7.5 ruamel.yaml-0.17.21 ruamel.yaml.clib-0.2.7 sly-0.4 sortedcontainers-2.4.0 spsdk-1.7.1 termcolor-2.2.0 tlv8-0.10.0 tqdm-4.65.0 typing_extensions-4.3.0 urllib3-1.26.15 wrapt-1.15.0
jas@kaka:~$
Then upgrading the device worked remarkable well, although I wish that the tool would have printed URLs and checksums for the firmware files to allow easy confirmation.
jas@kaka:~$ PATH=$PATH:/home/jas/.local/bin
jas@kaka:~$ nitropy start list
Command line tool to interact with Nitrokey devices 0.4.34
:: 'Nitrokey Start' keys:
FSIJ-1.2.15-5D271572: Nitrokey Nitrokey Start (RTM.12.1-RC2-modified)
jas@kaka:~$ nitropy start update
Command line tool to interact with Nitrokey devices 0.4.34
Nitrokey Start firmware update tool
Platform: Linux-5.15.0-67-generic-x86_64-with-glibc2.35
System: Linux, is_linux: True
Python: 3.10.6
Saving run log to: /tmp/nitropy.log.gc5753a8
Admin PIN:
Firmware data to be used:
- FirmwareType.REGNUAL: 4408, hash: ...b'72a30389' valid (from ...built/RTM.13/regnual.bin)
- FirmwareType.GNUK: 129024, hash: ...b'25a4289b' valid (from ...prebuilt/RTM.13/gnuk.bin)
Currently connected device strings:
Device:
Vendor: Nitrokey
Product: Nitrokey Start
Serial: FSIJ-1.2.15-5D271572
Revision: RTM.12.1-RC2-modified
Config: *:*:8e82
Sys: 3.0
Board: NITROKEY-START-G
initial device strings: [{'name': '', 'Vendor': 'Nitrokey', 'Product': 'Nitrokey Start', 'Serial': 'FSIJ-1.2.15-5D271572', 'Revision': 'RTM.12.1-RC2-modified', 'Config': '*:*:8e82', 'Sys': '3.0', 'Board': 'NITROKEY-START-G'}]
Please note:
- Latest firmware available is:
RTM.13 (published: 2022-12-08T10:59:11Z)
- provided firmware: None
- all data will be removed from the device!
- do not interrupt update process - the device may not run properly!
- the process should not take more than 1 minute
Do you want to continue? [yes/no]: yes
...
Starting bootloader upload procedure
Device: Nitrokey Start FSIJ-1.2.15-5D271572
Connected to the device
Running update!
Do NOT remove the device from the USB slot, until further notice
Downloading flash upgrade program...
Executing flash upgrade...
Waiting for device to appear:
Wait 20 seconds.....
Downloading the program
Protecting device
Finish flashing
Resetting device
Update procedure finished. Device could be removed from USB slot.
Currently connected device strings (after upgrade):
Device:
Vendor: Nitrokey
Product: Nitrokey Start
Serial: FSIJ-1.2.19-5D271572
Revision: RTM.13
Config: *:*:8e82
Sys: 3.0
Board: NITROKEY-START-G
device can now be safely removed from the USB slot
final device strings: [{'name': '', 'Vendor': 'Nitrokey', 'Product': 'Nitrokey Start', 'Serial': 'FSIJ-1.2.19-5D271572', 'Revision': 'RTM.13', 'Config': '*:*:8e82', 'Sys': '3.0', 'Board': 'NITROKEY-START-G'}]
finishing session 2023-03-16 21:49:07.371291
Log saved to: /tmp/nitropy.log.gc5753a8
jas@kaka:~$
jas@kaka:~$ nitropy start list
Command line tool to interact with Nitrokey devices 0.4.34
:: 'Nitrokey Start' keys:
FSIJ-1.2.19-5D271572: Nitrokey Nitrokey Start (RTM.13)
jas@kaka:~$
Before importing the master key to this device, it should be configured. Note the commands in the beginning to make sure scdaemon/pcscd is not running because they may have cached state from earlier cards. Change PIN code as you like after this, my experience with Gnuk was that the Admin PIN had to be changed first, then you import the key, and then you change the PIN.
jas@kaka:~$ gpg-connect-agent "SCD KILLSCD" "SCD BYE" /bye
OK
ERR 67125247 Slut på fil <GPG Agent>
jas@kaka:~$ ps auxww|grep -e pcsc -e scd
jas 11651 0.0 0.0 3468 1672 pts/0 R+ 21:54 0:00 grep --color=auto -e pcsc -e scd
jas@kaka:~$ gpg --card-edit
Reader ...........: 20A0:4211:FSIJ-1.2.19-5D271572:0
Application ID ...: D276000124010200FFFE5D2715720000
Application type .: OpenPGP
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 5D271572
Name of cardholder: [not set]
Language prefs ...: [not set]
Salutation .......:
URL of public key : [not set]
Login data .......: [not set]
Signature PIN ....: forced
Key attributes ...: rsa2048 rsa2048 rsa2048
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 0
KDF setting ......: off
Signature key ....: [none]
Encryption key....: [none]
Authentication key: [none]
General key info..: [none]
gpg/card> admin
Admin commands are allowed
gpg/card> kdf-setup
gpg/card> passwd
gpg: OpenPGP card no. D276000124010200FFFE5D2715720000 detected
1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit
Your selection? 3
PIN changed.
1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit
Your selection? q
gpg/card> name
Cardholder's surname: Josefsson
Cardholder's given name: Simon
gpg/card> lang
Language preferences: sv
gpg/card> sex
Salutation (M = Mr., F = Ms., or space): m
gpg/card> login
Login data (account name): jas
gpg/card> url
URL to retrieve public key: https://josefsson.org/key-20190320.txt
gpg/card> forcesig
gpg/card> key-attr
Changing card key attribute for: Signature key
Please select what kind of key you want:
(1) RSA
(2) ECC
Your selection? 2
Please select which elliptic curve you want:
(1) Curve 25519
(4) NIST P-384
Your selection? 1
The card will now be re-configured to generate a key of type: ed25519
Note: There is no guarantee that the card supports the requested size.
If the key generation does not succeed, please check the
documentation of your card to see what sizes are allowed.
Changing card key attribute for: Encryption key
Please select what kind of key you want:
(1) RSA
(2) ECC
Your selection? 2
Please select which elliptic curve you want:
(1) Curve 25519
(4) NIST P-384
Your selection? 1
The card will now be re-configured to generate a key of type: cv25519
Changing card key attribute for: Authentication key
Please select what kind of key you want:
(1) RSA
(2) ECC
Your selection? 2
Please select which elliptic curve you want:
(1) Curve 25519
(4) NIST P-384
Your selection? 1
The card will now be re-configured to generate a key of type: ed25519
gpg/card>
jas@kaka:~$ gpg --card-edit
Reader ...........: 20A0:4211:FSIJ-1.2.19-5D271572:0
Application ID ...: D276000124010200FFFE5D2715720000
Application type .: OpenPGP
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 5D271572
Name of cardholder: Simon Josefsson
Language prefs ...: sv
Salutation .......: Mr.
URL of public key : https://josefsson.org/key-20190320.txt
Login data .......: jas
Signature PIN ....: not forced
Key attributes ...: ed25519 cv25519 ed25519
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 0
KDF setting ......: on
Signature key ....: [none]
Encryption key....: [none]
Authentication key: [none]
General key info..: [none]
jas@kaka:~$
Once setup, bring out your offline machine and boot it and mount your USB stick with the offline key. The paths below will be different, and this is using a somewhat unorthodox approach of working with fresh GnuPG configuration paths that I chose for the USB stick.
jas@kaka:/media/jas/2c699cbd-b77e-4434-a0d6-0c4965864296$ cp -a gnupghome-backup-masterkey gnupghome-import-nitrokey-5D271572
jas@kaka:/media/jas/2c699cbd-b77e-4434-a0d6-0c4965864296$ gpg --homedir $PWD/gnupghome-import-nitrokey-5D271572 --edit-key B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE
gpg (GnuPG) 2.2.27; Copyright (C) 2021 Free Software Foundation, Inc.
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
Secret key is available.
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> keytocard
Really move the primary key? (y/N) y
Please select where to store the key:
(1) Signature key
(3) Authentication key
Your selection? 1
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg>
Save changes? (y/N) y
jas@kaka:/media/jas/2c699cbd-b77e-4434-a0d6-0c4965864296$
Don’t forget to change the PIN at this point. At this point it is useful to confirm that the Nitrokey has the master key available and that is possible to sign statements with it, back on your regular machine:
jas@kaka:~$ gpg --card-status
Reader ...........: 20A0:4211:FSIJ-1.2.19-5D271572:0
Application ID ...: D276000124010200FFFE5D2715720000
Application type .: OpenPGP
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 5D271572
Name of cardholder: Simon Josefsson
Language prefs ...: sv
Salutation .......: Mr.
URL of public key : https://josefsson.org/key-20190320.txt
Login data .......: jas
Signature PIN ....: not forced
Key attributes ...: ed25519 cv25519 ed25519
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 1
KDF setting ......: on
Signature key ....: B1D2 BD13 75BE CB78 4CF4 F8C4 D73C F638 C53C 06BE
created ....: 2019-03-20 23:37:24
Encryption key....: [none]
Authentication key: [none]
General key info..: pub ed25519/D73CF638C53C06BE 2019-03-20 Simon Josefsson <simon@josefsson.org>
sec> ed25519/D73CF638C53C06BE created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 5D271572
ssb> ed25519/80260EE8A9B92B2B created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 42315277
ssb> ed25519/51722B08FE4745A2 created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 42315277
ssb> cv25519/02923D7EE76EBD60 created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 42315277
jas@kaka:~$ echo foo|gpg -a --sign|gpg --verify
gpg: Signature made Thu Mar 16 22:11:02 2023 CET
gpg: using EDDSA key B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE
gpg: Good signature from "Simon Josefsson <simon@josefsson.org>" [ultimate]
jas@kaka:~$
Finally to retrieve and sign a key, for example Andre Heinecke’s that I could confirm the OpenPGP key identifier from his business card.
jas@kaka:~$ gpg --locate-external-keys aheinecke@gnupg.com
gpg: key 1FDF723CF462B6B1: public key "Andre Heinecke <aheinecke@gnupg.com>" imported
gpg: Total number processed: 1
gpg: imported: 1
gpg: marginals needed: 3 completes needed: 1 trust model: pgp
gpg: depth: 0 valid: 2 signed: 7 trust: 0-, 0q, 0n, 0m, 0f, 2u
gpg: depth: 1 valid: 7 signed: 64 trust: 7-, 0q, 0n, 0m, 0f, 0u
gpg: next trustdb check due at 2023-05-26
pub rsa3072 2015-12-08 [SC] [expires: 2025-12-05]
94A5C9A03C2FE5CA3B095D8E1FDF723CF462B6B1
uid [ unknown] Andre Heinecke <aheinecke@gnupg.com>
sub ed25519 2017-02-13 [S]
sub ed25519 2017-02-13 [A]
sub rsa3072 2015-12-08 [E] [expires: 2025-12-05]
sub rsa3072 2015-12-08 [A] [expires: 2025-12-05]
jas@kaka:~$ gpg --edit-key "94A5C9A03C2FE5CA3B095D8E1FDF723CF462B6B1"
gpg (GnuPG) 2.2.27; Copyright (C) 2021 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.
pub rsa3072/1FDF723CF462B6B1
created: 2015-12-08 expires: 2025-12-05 usage: SC
trust: unknown validity: unknown
sub ed25519/2978E9D40CBABA5C
created: 2017-02-13 expires: never usage: S
sub ed25519/DC74D901C8E2DD47
created: 2017-02-13 expires: never usage: A
The following key was revoked on 2017-02-23 by RSA key 1FDF723CF462B6B1 Andre Heinecke <aheinecke@gnupg.com>
sub cv25519/1FFE3151683260AB
created: 2017-02-13 revoked: 2017-02-23 usage: E
sub rsa3072/8CC999BDAA45C71F
created: 2015-12-08 expires: 2025-12-05 usage: E
sub rsa3072/6304A4B539CE444A
created: 2015-12-08 expires: 2025-12-05 usage: A
[ unknown] (1). Andre Heinecke <aheinecke@gnupg.com>
gpg> sign
pub rsa3072/1FDF723CF462B6B1
created: 2015-12-08 expires: 2025-12-05 usage: SC
trust: unknown validity: unknown
Primary key fingerprint: 94A5 C9A0 3C2F E5CA 3B09 5D8E 1FDF 723C F462 B6B1
Andre Heinecke <aheinecke@gnupg.com>
This key is due to expire on 2025-12-05.
Are you sure that you want to sign this key with your
key "Simon Josefsson <simon@josefsson.org>" (D73CF638C53C06BE)
Really sign? (y/N) y
gpg> quit
Save changes? (y/N) y
jas@kaka:~$
This is on my day-to-day machine, using the NitroKey Start with the offline key. No need to boot the old offline machine just to sign keys or extend expiry anymore! At FOSDEM’23 I managed to get at least one DD signature on my new key, and the Debian keyring maintainers accepted my Ed25519 key. Hopefully I can now finally let my 2014-era RSA3744 key expire in 2023-09-19 and not extend it any further. This should finish my transition to a simpler OpenPGP key setup, yay!
I use GnuPG to compute cryptographic signatures for my emails, git commits/tags, and software release artifacts (tarballs). Part of GnuPG is gpg-agent which talks to OpenSSH, which I login to remote servers and to clone git repositories. I dislike storing cryptographic keys on general-purpose machines, and have used hardware-backed OpenPGP keys since around 2006 when I got a FSFE Fellowship Card. GnuPG via gpg-agent handles this well, and the private key never leaves the hardware. The ZeitControl cards were (to my knowledge) proprietary hardware running some non-free operating system and OpenPGP implementation. By late 2012 the YubiKey NEO supported OpenPGP, and while the hardware and operating system on it was not free, at least it ran a free software OpenPGP implementation and eventually I setup my primary RSA key on it. This worked well for a couple of years, and when I in 2019 wished to migrate to a new key, the FST-01G device with open hardware running free software that supported Ed25519 had become available. I created a key and have been using the FST-01G on my main laptop since then. This little device has been working, the signature counter on it is around 14501 which means around 10 signatures/day since then!
Currently I am in the process of migrating towards a new laptop, and moving the FST-01G device between them is cumbersome, especially if I want to use both laptops in parallel. That’s why I need to setup a new hardware device to hold my OpenPGP key, which can go with my new laptop. This is a good time to re-visit alternatives. I quickly decided that I did not want to create a new key, only to import my current one to keep everything working. My requirements on the device to chose hasn’t changed since 2019, see my summary at the end of the earlier blog post. Unfortunately the FST-01G is out of stock and the newer FST-01SZ has also out of stock. While Tillitis looks promising (and I have one to play with), it does not support OpenPGP (yet). What to do? Fortunately, I found some FST-01SZ device in my drawer, and decided to use it pending a more satisfactory answer. Hopefully once I get around to generate a new OpenPGP key in a year or so, I will do a better survey of options that are available on the market then. What are your (freedom-respecting) OpenPGP hardware recommendations?
FST-01SZ circuit board
Similar to setting up the FST-01G, the FST-01SZ needs to be setup before use. I’m doing the following from Trisquel 11 but any GNU/Linux system would work. When the device is inserted at first time, some kernel messages are shown (see /var/log/syslog or use the dmesg command):
usb 3-3: new full-speed USB device number 39 using xhci_hcd
usb 3-3: New USB device found, idVendor=234b, idProduct=0004, bcdDevice= 2.00
usb 3-3: New USB device strings: Mfr=1, Product=2, SerialNumber=3
usb 3-3: Product: Fraucheky
usb 3-3: Manufacturer: Free Software Initiative of Japan
usb 3-3: SerialNumber: FSIJ-0.0
usb-storage 3-3:1.0: USB Mass Storage device detected
scsi host1: usb-storage 3-3:1.0
scsi 1:0:0:0: Direct-Access FSIJ Fraucheky 1.0 PQ: 0 ANSI: 0
sd 1:0:0:0: Attached scsi generic sg2 type 0
sd 1:0:0:0: [sdc] 128 512-byte logical blocks: (65.5 kB/64.0 KiB)
sd 1:0:0:0: [sdc] Write Protect is off
sd 1:0:0:0: [sdc] Mode Sense: 03 00 00 00
sd 1:0:0:0: [sdc] No Caching mode page found
sd 1:0:0:0: [sdc] Assuming drive cache: write through
sdc:
sd 1:0:0:0: [sdc] Attached SCSI removable disk
Interestingly, the NeuG software installed on the device I got appears to be version 1.0.9:
jas@kaka:~$ head /media/jas/Fraucheky/README
NeuG - a true random number generator implementation
Version 1.0.9
2018-11-20
Niibe Yutaka
Free Software Initiative of Japan
What's NeuG?
============
jas@kaka:~$
I could not find version 1.0.9 published anywhere, but the device came with a SD-card that contain a copy of the source, so I uploaded it until a more canonical place is located. Putting the device in the serial mode can be done using a sudo eject /dev/sdc command which results in the following syslog output.
usb 3-3: reset full-speed USB device number 39 using xhci_hcd
usb 3-3: device firmware changed
usb 3-3: USB disconnect, device number 39
sdc: detected capacity change from 128 to 0
usb 3-3: new full-speed USB device number 40 using xhci_hcd
usb 3-3: New USB device found, idVendor=234b, idProduct=0001, bcdDevice= 2.00
usb 3-3: New USB device strings: Mfr=1, Product=2, SerialNumber=3
usb 3-3: Product: NeuG True RNG
usb 3-3: Manufacturer: Free Software Initiative of Japan
usb 3-3: SerialNumber: FSIJ-1.0.9-42315277
cdc_acm 3-3:1.0: ttyACM0: USB ACM device
Now download Gnuk, verify its integrity and build it. You may need some additional packages installed, try apt-get install gcc-arm-none-eabi openocd python3-usb. As you can see, I’m using the stable 1.2 branch of Gnuk, currently on version 1.2.20. The ./configure parameters deserve some explanation. The kdf_do=required sets up the device to require KDF usage. The --enable-factory-reset allows me to use the command factory-reset (with admin PIN) inside gpg --card-edit to completely wipe the card. Some may consider that too dangerous, but my view is that if someone has your admin PIN it is game over anyway. The --vidpid=234b:0000 is specifies the USB VID/PID to use, and --target=FST_01SZ is critical to set the platform (you’ll may brick the device if you pick the wrong --target setting).
jas@kaka:~/src$ rm -rf gnuk neug
jas@kaka:~/src$ git clone https://gitlab.com/jas/neug.git
Cloning into 'neug'...
remote: Enumerating objects: 2034, done.
remote: Counting objects: 100% (2034/2034), done.
remote: Compressing objects: 100% (603/603), done.
remote: Total 2034 (delta 1405), reused 2013 (delta 1405), pack-reused 0
Receiving objects: 100% (2034/2034), 910.34 KiB | 3.50 MiB/s, done.
Resolving deltas: 100% (1405/1405), done.
jas@kaka:~/src$ git clone https://salsa.debian.org/gnuk-team/gnuk/gnuk.git
Cloning into 'gnuk'...
remote: Enumerating objects: 13765, done.
remote: Counting objects: 100% (959/959), done.
remote: Compressing objects: 100% (337/337), done.
remote: Total 13765 (delta 629), reused 907 (delta 599), pack-reused 12806
Receiving objects: 100% (13765/13765), 12.59 MiB | 3.05 MiB/s, done.
Resolving deltas: 100% (10077/10077), done.
jas@kaka:~/src$ cd neug
jas@kaka:~/src/neug$ git describe
release/1.0.9
jas@kaka:~/src/neug$ git tag -v `git describe`
object 5d51022a97a5b7358d0ea62bbbc00628c6cec06a
type commit
tag release/1.0.9
tagger NIIBE Yutaka <gniibe@fsij.org> 1542701768 +0900
Version 1.0.9.
gpg: Signature made Tue Nov 20 09:16:08 2018 CET
gpg: using EDDSA key 249CB3771750745D5CDD323CE267B052364F028D
gpg: issuer "gniibe@fsij.org"
gpg: Good signature from "NIIBE Yutaka <gniibe@fsij.org>" [unknown]
gpg: aka "NIIBE Yutaka <gniibe@debian.org>" [unknown]
gpg: WARNING: This key is not certified with a trusted signature!
gpg: There is no indication that the signature belongs to the owner.
Primary key fingerprint: 249C B377 1750 745D 5CDD 323C E267 B052 364F 028D
jas@kaka:~/src/neug$ cd ../gnuk/
jas@kaka:~/src/gnuk$ git checkout STABLE-BRANCH-1-2
Branch 'STABLE-BRANCH-1-2' set up to track remote branch 'STABLE-BRANCH-1-2' from 'origin'.
Switched to a new branch 'STABLE-BRANCH-1-2'
jas@kaka:~/src/gnuk$ git describe
release/1.2.20
jas@kaka:~/src/gnuk$ git tag -v `git describe`
object 9d3c08bd2beb73ce942b016d4328f0a596096c02
type commit
tag release/1.2.20
tagger NIIBE Yutaka <gniibe@fsij.org> 1650594032 +0900
Gnuk: Version 1.2.20
gpg: Signature made Fri Apr 22 04:20:32 2022 CEST
gpg: using EDDSA key 249CB3771750745D5CDD323CE267B052364F028D
gpg: Good signature from "NIIBE Yutaka <gniibe@fsij.org>" [unknown]
gpg: aka "NIIBE Yutaka <gniibe@debian.org>" [unknown]
gpg: WARNING: This key is not certified with a trusted signature!
gpg: There is no indication that the signature belongs to the owner.
Primary key fingerprint: 249C B377 1750 745D 5CDD 323C E267 B052 364F 028D
jas@kaka:~/src/gnuk/src$ git submodule update --init
Submodule 'chopstx' (https://salsa.debian.org/gnuk-team/chopstx/chopstx.git) registered for path '../chopstx'
Cloning into '/home/jas/src/gnuk/chopstx'...
Submodule path '../chopstx': checked out 'e12a7e0bb3f004c7bca41cfdb24c8b66daf3db89'
jas@kaka:~/src/gnuk$ cd chopstx
jas@kaka:~/src/gnuk/chopstx$ git describe
release/1.21
jas@kaka:~/src/gnuk/chopstx$ git tag -v `git describe`
object e12a7e0bb3f004c7bca41cfdb24c8b66daf3db89
type commit
tag release/1.21
tagger NIIBE Yutaka <gniibe@fsij.org> 1650593697 +0900
Chopstx: Version 1.21
gpg: Signature made Fri Apr 22 04:14:57 2022 CEST
gpg: using EDDSA key 249CB3771750745D5CDD323CE267B052364F028D
gpg: Good signature from "NIIBE Yutaka <gniibe@fsij.org>" [unknown]
gpg: aka "NIIBE Yutaka <gniibe@debian.org>" [unknown]
gpg: WARNING: This key is not certified with a trusted signature!
gpg: There is no indication that the signature belongs to the owner.
Primary key fingerprint: 249C B377 1750 745D 5CDD 323C E267 B052 364F 028D
jas@kaka:~/src/gnuk/chopstx$ cd ../src
jas@kaka:~/src/gnuk/src$ kdf_do=required ./configure --enable-factory-reset --vidpid=234b:0000 --target=FST_01SZ
Header file is: board-fst-01sz.h
Debug option disabled
Configured for bare system (no-DFU)
PIN pad option disabled
CERT.3 Data Object is NOT supported
Card insert/removal by HID device is NOT supported
Life cycle management is supported
Acknowledge button is supported
KDF DO is required before key import/generation
jas@kaka:~/src/gnuk/src$ make | less
jas@kaka:~/src/gnuk/src$ cd ../regnual/
jas@kaka:~/src/gnuk/regnual$ make | less
jas@kaka:~/src/gnuk/regnual$ cd ../../
jas@kaka:~/src$ sudo python3 neug/tool/neug_upgrade.py -f gnuk/regnual/regnual.bin gnuk/src/build/gnuk.bin
gnuk/regnual/regnual.bin: 4608
gnuk/src/build/gnuk.bin: 109568
CRC32: b93ca829
Device:
Configuration: 1
Interface: 1
20000e00:20005000
Downloading flash upgrade program...
start 20000e00
end 20002000
# 20002000: 32 : 4
Run flash upgrade program...
Wait 1 second...
Wait 1 second...
Device:
08001000:08020000
Downloading the program
start 08001000
end 0801ac00
jas@kaka:~/src$
The kernel log will contain the following, and the card is ready to use as an OpenPGP card. You may unplug it and re-insert it as you wish.
usb 3-3: reset full-speed USB device number 41 using xhci_hcd
usb 3-3: device firmware changed
usb 3-3: USB disconnect, device number 41
usb 3-3: new full-speed USB device number 42 using xhci_hcd
usb 3-3: New USB device found, idVendor=234b, idProduct=0000, bcdDevice= 2.00
usb 3-3: New USB device strings: Mfr=1, Product=2, SerialNumber=3
usb 3-3: Product: Gnuk Token
usb 3-3: Manufacturer: Free Software Initiative of Japan
usb 3-3: SerialNumber: FSIJ-1.2.20-42315277
Setting up the card is the next step, and there are many tutorials around for this, eventually I settled with the following sequence. Let’s start with setting the admin PIN. First make sure that pcscd nor scdaemon is running, which is good hygien since those processes cache some information and with a stale connection this easily leads to confusion. Cache invalidation… sigh.
jas@kaka:~$ gpg-connect-agent "SCD KILLSCD" "SCD BYE" /bye
jas@kaka:~$ ps auxww|grep -e pcsc -e scd
jas 30221 0.0 0.0 3468 1692 pts/3 R+ 11:49 0:00 grep --color=auto -e pcsc -e scd
jas@kaka:~$ gpg --card-edit
Reader ...........: 234B:0000:FSIJ-1.2.20-42315277:0
Application ID ...: D276000124010200FFFE423152770000
Application type .: OpenPGP
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 42315277
Name of cardholder: [not set]
Language prefs ...: [not set]
Salutation .......:
URL of public key : [not set]
Login data .......: [not set]
Signature PIN ....: forced
Key attributes ...: rsa2048 rsa2048 rsa2048
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 0
KDF setting ......: off
Signature key ....: [none]
Encryption key....: [none]
Authentication key: [none]
General key info..: [none]
gpg/card> admin
Admin commands are allowed
gpg/card> kdf-setup
gpg/card> passwd
gpg: OpenPGP card no. D276000124010200FFFE423152770000 detected
1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit
Your selection? 3
PIN changed.
1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit
Your selection?
Now it would be natural to setup the PIN and reset code. However the Gnuk software is configured to not allow this until the keys are imported. You would get the following somewhat cryptical error messages if you try. This took me a while to understand, since this is device-specific, and some other OpenPGP implementations allows you to configure a PIN and reset code before key import.
Your selection? 4
Error setting the Reset Code: Card error
1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit
Your selection? 1
Error changing the PIN: Conditions of use not satisfied
1 - change PIN
2 - unblock PIN
3 - change Admin PIN
4 - set the Reset Code
Q - quit
Your selection? q
Continue to configure the card and make it ready for key import. Some settings deserve comments. The lang field may be used to setup the language, but I have rarely seen it use, and I set it to ‘sv‘ (Swedish) mostly to be able to experiment if any software adhears to it. The URL is important to point to somewhere where your public key is stored, the fetch command of gpg --card-edit downloads it and sets up GnuPG with it when you are on a clean new laptop. The forcesig command changes the default so that a PIN code is not required for every digital signature operation, remember that I averaged 10 signatures per day for the past 2-3 years? Think of the wasted energy typing those PIN codes every time! Changing the cryptographic key type is required when I import 25519-based keys.
gpg/card> name
Cardholder's surname: Josefsson
Cardholder's given name: Simon
gpg/card> lang
Language preferences: sv
gpg/card> sex
Salutation (M = Mr., F = Ms., or space): m
gpg/card> login
Login data (account name): jas
gpg/card> url
URL to retrieve public key: https://josefsson.org/key-20190320.txt
gpg/card> forcesig
gpg/card> key-attr
Changing card key attribute for: Signature key
Please select what kind of key you want:
(1) RSA
(2) ECC
Your selection? 2
Please select which elliptic curve you want:
(1) Curve 25519
(4) NIST P-384
Your selection? 1
The card will now be re-configured to generate a key of type: ed25519
Note: There is no guarantee that the card supports the requested size.
If the key generation does not succeed, please check the
documentation of your card to see what sizes are allowed.
Changing card key attribute for: Encryption key
Please select what kind of key you want:
(1) RSA
(2) ECC
Your selection? 2
Please select which elliptic curve you want:
(1) Curve 25519
(4) NIST P-384
Your selection? 1
The card will now be re-configured to generate a key of type: cv25519
Changing card key attribute for: Authentication key
Please select what kind of key you want:
(1) RSA
(2) ECC
Your selection? 2
Please select which elliptic curve you want:
(1) Curve 25519
(4) NIST P-384
Your selection? 1
The card will now be re-configured to generate a key of type: ed25519
gpg/card>
Reader ...........: 234B:0000:FSIJ-1.2.20-42315277:0
Application ID ...: D276000124010200FFFE423152770000
Application type .: OpenPGP
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 42315277
Name of cardholder: Simon Josefsson
Language prefs ...: sv
Salutation .......: Mr.
URL of public key : https://josefsson.org/key-20190320.txt
Login data .......: jas
Signature PIN ....: not forced
Key attributes ...: ed25519 cv25519 ed25519
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 0
KDF setting ......: on
Signature key ....: [none]
Encryption key....: [none]
Authentication key: [none]
General key info..: [none]
gpg/card>
The device is now ready for key import! Bring out your offline laptop and boot it and use the keytocard command on the subkeys to import them. This assumes you saved a copy of the GnuPG home directory after generating the master and subkeys before, which I did in my own previous tutorial when I generated the keys. This may be a bit unusual, and there are simpler ways to do this (e.g., import a copy of the secret keys into a fresh GnuPG home directory).
$ cp -a gnupghome-backup-mastersubkeys gnupghome-import-fst01sz-42315277-2022-12-24
$ ps auxww|grep -e pcsc -e scd
$ gpg --homedir $PWD/gnupghome-import-fst01sz-42315277-2022-12-24 --edit-key B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE
...
Secret key is available.
gpg: checking the trustdb
gpg: marginals needed: 3 completes needed: 1 trust model: pgp
gpg: depth: 0 valid: 1 signed: 0 trust: 0-, 0q, 0n, 0m, 0f, 1u
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> key 1
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb* cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> keytocard
Please select where to store the key:
(2) Encryption key
Your selection? 2
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb* cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> key 1
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> key 2
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb* ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> keytocard
Please select where to store the key:
(3) Authentication key
Your selection? 3
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb* ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> key 2
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> key 3
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb* ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> keytocard
Please select where to store the key:
(1) Signature key
(3) Authentication key
Your selection? 1
sec ed25519/D73CF638C53C06BE
created: 2019-03-20 expired: 2019-10-22 usage: SC
trust: ultimate validity: expired
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expired: 2019-10-22 usage: E
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expired: 2019-10-22 usage: A
ssb* ed25519/51722B08FE4745A2
created: 2019-03-20 expired: 2019-10-22 usage: S
[ expired] (1). Simon Josefsson <simon@josefsson.org>
gpg> quit
Save changes? (y/N) y
$
Now insert it into your daily laptop and have GnuPG and learn about the new private keys and forget about any earlier locally available card bindings — this usually manifests itself by GnuPG asking you to insert a OpenPGP card with another serial number. Earlier I did rm -rf ~/.gnupg/private-keys-v1.d/ but the scd serialno followed by learn --force is nicer. I also sets up trust setting for my own key.
jas@kaka:~$ gpg-connect-agent "scd serialno" "learn --force" /bye
...
jas@kaka:~$ echo "B1D2BD1375BECB784CF4F8C4D73CF638C53C06BE:6:" | gpg --import-ownertrust
jas@kaka:~$ gpg --card-status
Reader ...........: 234B:0000:FSIJ-1.2.20-42315277:0
Application ID ...: D276000124010200FFFE423152770000
Application type .: OpenPGP
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 42315277
Name of cardholder: Simon Josefsson
Language prefs ...: sv
Salutation .......: Mr.
URL of public key : https://josefsson.org/key-20190320.txt
Login data .......: jas
Signature PIN ....: not forced
Key attributes ...: ed25519 cv25519 ed25519
Max. PIN lengths .: 127 127 127
PIN retry counter : 5 5 5
Signature counter : 3
KDF setting ......: on
Signature key ....: A3CC 9C87 0B9D 310A BAD4 CF2F 5172 2B08 FE47 45A2
created ....: 2019-03-20 23:40:49
Encryption key....: A9EC 8F4D 7F1E 50ED 3DEF 49A9 0292 3D7E E76E BD60
created ....: 2019-03-20 23:40:26
Authentication key: CA7E 3716 4342 DF31 33DF 3497 8026 0EE8 A9B9 2B2B
created ....: 2019-03-20 23:40:37
General key info..: sub ed25519/51722B08FE4745A2 2019-03-20 Simon Josefsson <simon@josefsson.org>
sec# ed25519/D73CF638C53C06BE created: 2019-03-20 expires: 2023-09-19
ssb> ed25519/80260EE8A9B92B2B created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 42315277
ssb> ed25519/51722B08FE4745A2 created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 42315277
ssb> cv25519/02923D7EE76EBD60 created: 2019-03-20 expires: 2023-09-19
card-no: FFFE 42315277
jas@kaka:~$
Verify that you can digitally sign and authenticate using the key and you are done!
jas@kaka:~$ echo foo|gpg -a --sign|gpg --verify
gpg: Signature made Sat Dec 24 13:49:59 2022 CET
gpg: using EDDSA key A3CC9C870B9D310ABAD4CF2F51722B08FE4745A2
gpg: Good signature from "Simon Josefsson <simon@josefsson.org>" [ultimate]
jas@kaka:~$ ssh-add -L
ssh-ed25519 AAAAC3NzaC1lZDI1NTE5AAAAILzCFcHHrKzVSPDDarZPYqn89H5TPaxwcORgRg+4DagE cardno:FFFE42315277
jas@kaka:~$
So time to relax and celebrate christmas? Hold on… not so fast! Astute readers will have noticed that the output said ‘PIN retry counter: 5 5 5‘. That’s not the default PIN retry counter for Gnuk! How did that happen? Indeed, good catch and great question, my dear reader. I wanted to include how you can modify the Gnuk source code, re-build it and re-flash the Gnuk as well. This method is different than flashing Gnuk onto a device that is running NeuG so the commands I used to flash the firmware in the start of this blog post no longer works in a device running Gnuk. Fortunately modern Gnuk supports updating firmware by specifying the Admin PIN code only, and provides a simple script to achieve this as well. The PIN retry counter setting is hard coded in the openpgp-do.c file, and we run a a perl command to modify the file, rebuild Gnuk and upgrade the FST-01SZ. This of course wipes all your settings, so you will have the opportunity to practice all the commands earlier in this post once again!
jas@kaka:~/src/gnuk/src$ perl -pi -e 's/PASSWORD_ERRORS_MAX 3/PASSWORD_ERRORS_MAX 5/' openpgp-do.c
jas@kaka:~/src/gnuk/src$ make | less
jas@kaka:~/src/gnuk/src$ cd ../tool/
jas@kaka:~/src/gnuk/tool$ ./upgrade_by_passwd.py
Admin password:
Device:
Configuration: 1
Interface: 0
../regnual/regnual.bin: 4608
../src/build/gnuk.bin: 110592
CRC32: b93ca829
Device:
Configuration: 1
Interface: 0
20002a00:20005000
Downloading flash upgrade program...
start 20002a00
end 20003c00
Run flash upgrade program...
Waiting for device to appear:
Wait 1 second...
Wait 1 second...
Device:
08001000:08020000
Downloading the program
start 08001000
end 0801b000
Protecting device
Finish flashing
Resetting device
Update procedure finished
jas@kaka:~/src/gnuk/tool$
Now finally, I wish you all a Merry Christmas and Happy Hacking!
The Debian operating system is what I have been using on my main computer for what is probably around 20 years. I am now in the process of installing the hopefully soon released Debian 11 “bullseye” on my Lenovo X201 laptop. Getting a OpenPGP smartcard to work has almost always required some additional effort, but it has been reliable enough to use exclusively for my daily GnuPG and SSH operations since 2006. In the early days, the issues with smartcards were not related to GNOME, see my smartcard notes for Debian 4 Etch for example. I believe with Debian 5 Lenny, Debian 6 Squeeze, and Debian 7 Stretch things just worked without workarounds, even with GNOME. Those were the golden days! Back in 2015, with Debian 8 Jessie I noticed a regression and came up with a workaround. The problems in GNOME were not fixed, and I wrote about how to work around this for Debian 9 Stretch and the slightly different workaround needed for Debian 10 Buster. What will Bullseye be like?
The first impression of working with GnuPG and a smartcard is still the same. After inserting the GNUK that holds my private keys into my laptop, nothing happens by default and attempting to access the smartcard results in the following.
jas@latte:~$ gpg --card-status
gpg: error getting version from 'scdaemon': No SmartCard daemon
gpg: OpenPGP card not available: No SmartCard daemon
jas@latte:~$
The solution is to install the scdaemon package. My opinion is that either something should offer to install it when the device is inserted (wasn’t there a framework for discovering hardware and installing the right packages?) or this package should always be installed for a desktop system. Anyway, the following solves the problem.
jas@latte:~$ sudo apt install scdaemon
...
jas@latte:~$ gpg --card-status
Reader ………..: 234B:0000:FSIJ-1.2.14-67252015:0
Application ID …: D276000124010200FFFE672520150000
...
URL of public key : https://josefsson.org/key-20190320.txt
...
Before the private key in the smartcard can be used, the public key must be imported into GnuPG. I now believe the best way to do this (see earlier posts for alternatives) is to configure the smartcard with a public key URL and retrieve it as follows.
The next step is to mark your own key as ultimately trusted, use the fingerprint shown above together with gpg --import-ownertrust. Warning! This is not the general way to remove the warning about untrusted keys, this method should only be used for your own keys.
Now GnuPG is able to both sign, encrypt, and decrypt data:
jas@latte:~$ echo foo|gpg -a --sign|gpg --verify
gpg: Signature made Sat May 1 16:02:49 2021 CEST
gpg: using EDDSA key A3CC9C870B9D310ABAD4CF2F51722B08FE4745A2
gpg: Good signature from "Simon Josefsson simon@josefsson.org" [ultimate]
jas@latte:~$ echo foo|gpg -a --encrypt -r simon@josefsson.org|gpg --decrypt
gpg: encrypted with 256-bit ECDH key, ID 02923D7EE76EBD60, created 2019-03-20
"Simon Josefsson simon@josefsson.org"
foo
jas@latte:~$
To make SSH work with the smartcard, the following is the GNOME-related workaround that is still required. The problem is that the GNOME keyring enables its own incomplete SSH-agent implementation. It is lacking the smartcard support that the GnuPG agent can provide, and even set the SSH_AUTH_SOCK environment variable if the enable-ssh-support parameter is provided.
jas@latte:~$ ssh-add -L
The agent has no identities.
jas@latte:~$ echo $SSH_AUTH_SOCK
/run/user/1000/keyring/ssh
jas@latte:~$ mkdir -p ~/.config/autostart
jas@latte:~$ cp /etc/xdg/autostart/gnome-keyring-ssh.desktop ~/.config/autostart/
jas@latte:~$ echo 'Hidden=true' >> .config/autostart/gnome-keyring-ssh.desktop
jas@latte:~$ echo enable-ssh-support >> ~/.gnupg/gpg-agent.conf
For some reason, it does not seem sufficient to log out of GNOME and then login again. Most likely some daemon is still running, that has to be restarted. At this point, I reboot my laptop and then log into GNOME again. Finally it looks correct:
Please discuss in small groups the following topics:
How should the scdaemon package be installed more automatically?
Should there a simple command to retrieve the public key for a smartcard and set it as ultimately trusted? The two step --card-edit and --import-ownertrust steps is a bad user interface and is not intuitive in my opinion.
Why is GNOME keyring used for SSH keys instead of ssh-agent/gpg-agent?
Should gpg-agent have enable-ssh-support on by default?
After these years, I would probably feel a bit of sadness if the problems were fixed, since then I wouldn’t be able to rant about this problem and celebrate installing Debian 12 Bookworm the same way I have done for the some past releases.
Debian buster is almost released, and today I celebrate midsummer by installing (a pre-release) of it on my Lenovo X201 laptop. Everything went smooth, except for the usual issues with smartcards under GNOME. I use a FST-01G running Gnuk, but the same issue apply to all OpenPGP cards including YubiKeys. I wrote about this problem for earlier releases, read Smartcards on Debian 9 Stretch and Smartcards on Debian 8 Jessie. Some things have changed – now GnuPG‘s internal ccid support works, and dirmngr is installed by default when you install Debian with GNOME. I thought I’d write a new post for the new release.
After installing Debian and logging into GNOME, I start a terminal and attempt to use the smartcard as follows.
jas@latte:~$ gpg --card-status
gpg: error getting version from 'scdaemon': No SmartCard daemon
gpg: OpenPGP card not available: No SmartCard daemon
jas@latte:~$
The reason is that the scdaemon package is not installed. Install it as follows.
jas@latte:~$ sudo apt-get install scdaemon
After this, gpg --card-status works. It is now using GnuPG’s internal CCID library, which appears to be working. The pcscd package is not required to get things working any more — however installing it also works, and you might need pcscd if you use other applications that talks to the smartcard.
jas@latte:~$ gpg --card-status
Reader ...........: Free Software Initiative of Japan Gnuk (FSIJ-1.2.14-67252015) 00 00
Application ID ...: D276000124010200FFFE672520150000
Version ..........: 2.0
Manufacturer .....: unmanaged S/N range
Serial number ....: 67252015
Name of cardholder: Simon Josefsson
Language prefs ...: sv
Sex ..............: man
URL of public key : https://josefsson.org/key-20190320.txt
Login data .......: jas
Signature PIN ....: inte tvingad
Key attributes ...: ed25519 cv25519 ed25519
Max. PIN lengths .: 127 127 127
PIN retry counter : 3 3 3
Signature counter : 710
KDF setting ......: off
Signature key ....: A3CC 9C87 0B9D 310A BAD4 CF2F 5172 2B08 FE47 45A2
created ....: 2019-03-20 23:40:49
Encryption key....: A9EC 8F4D 7F1E 50ED 3DEF 49A9 0292 3D7E E76E BD60
created ....: 2019-03-20 23:40:26
Authentication key: CA7E 3716 4342 DF31 33DF 3497 8026 0EE8 A9B9 2B2B
created ....: 2019-03-20 23:40:37
General key info..: [none]
jas@latte:~$
As before, using the key does not work right away:
jas@latte:~$ echo foo|gpg -a --sign
gpg: no default secret key: No public key
gpg: signing failed: No public key
jas@latte:~$
This is because GnuPG does not have the public key that correspond to the private key inside the smartcard.
You may retrieve your public key from the clouds as follows. With Debian Buster, the dirmngr package is installed by default so there is no need to install it. Alternatively, if you configured your smartcard with a public key URL that works, you may type “retrieve” into the gpg --card-edit interactive interface. This could be considered slightly more reliable (at least from a self-hosting point of view), because it uses your configured URL for retrieving the public key rather than trusting clouds.
Now signing with the smart card works! Yay! Btw: compare the output size with the output size in the previous post to understand the size advantage with Ed25519 over RSA.
As before, encrypting to myself does not work smoothly because of the trust setting on the public key. Witness the problem here:
jas@latte:~$ echo foo|gpg -a --encrypt -r simon@josefsson.org
gpg: 02923D7EE76EBD60: There is no assurance this key belongs to the named user
sub cv25519/02923D7EE76EBD60 2019-03-20 Simon Josefsson <simon@josefsson.org>
Primary key fingerprint: B1D2 BD13 75BE CB78 4CF4 F8C4 D73C F638 C53C 06BE
Subkey fingerprint: A9EC 8F4D 7F1E 50ED 3DEF 49A9 0292 3D7E E76E BD60
It is NOT certain that the key belongs to the person named
in the user ID. If you *really* know what you are doing,
you may answer the next question with yes.
Use this key anyway? (y/N)
gpg: signal Interrupt caught ... exiting
jas@latte:~$
You update the trust setting with the gpg --edit-key command. Take note that this is not the general way of getting rid of the “There is no assurance this key belongs to the named user” warning — using a ultimate trust setting is normally only relevant for your own keys, which is the case here.
jas@latte:~$ gpg --edit-key simon@josefsson.org
gpg (GnuPG) 2.2.12; Copyright (C) 2018 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 subkeys are available.
pub ed25519/D73CF638C53C06BE
created: 2019-03-20 expires: 2019-10-22 usage: SC
trust: unknown validity: unknown
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expires: 2019-10-22 usage: E
card-no: FFFE 67252015
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expires: 2019-10-22 usage: A
card-no: FFFE 67252015
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expires: 2019-10-22 usage: S
card-no: FFFE 67252015
[ unknown] (1). Simon Josefsson <simon@josefsson.org>
gpg> trust
pub ed25519/D73CF638C53C06BE
created: 2019-03-20 expires: 2019-10-22 usage: SC
trust: unknown validity: unknown
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expires: 2019-10-22 usage: E
card-no: FFFE 67252015
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expires: 2019-10-22 usage: A
card-no: FFFE 67252015
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expires: 2019-10-22 usage: S
card-no: FFFE 67252015
[ unknown] (1). Simon Josefsson <simon@josefsson.org>
Please decide how far you trust this user to correctly verify other users' keys
(by looking at passports, checking fingerprints from different sources, etc.)
1 = I don't know or won't say
2 = I do NOT trust
3 = I trust marginally
4 = I trust fully
5 = I trust ultimately
m = back to the main menu
Your decision? 5
Do you really want to set this key to ultimate trust? (y/N) y
pub ed25519/D73CF638C53C06BE
created: 2019-03-20 expires: 2019-10-22 usage: SC
trust: ultimate validity: unknown
ssb cv25519/02923D7EE76EBD60
created: 2019-03-20 expires: 2019-10-22 usage: E
card-no: FFFE 67252015
ssb ed25519/80260EE8A9B92B2B
created: 2019-03-20 expires: 2019-10-22 usage: A
card-no: FFFE 67252015
ssb ed25519/51722B08FE4745A2
created: 2019-03-20 expires: 2019-10-22 usage: S
card-no: FFFE 67252015
[ unknown] (1). Simon Josefsson <simon@josefsson.org>
Please note that the shown key validity is not necessarily correct
unless you restart the program.
gpg> quit
jas@latte:~$
Confirm gpg --list-keys indicate that the key is now trusted, and encrypting to yourself should work.
The issue with OpenSSH and GNOME Keyring still exists as in previous releases.
jas@latte:~$ ssh-add -L
The agent has no identities.
jas@latte:~$ echo $SSH_AUTH_SOCK
/run/user/1000/keyring/ssh
jas@latte:~$
The trick we used last time still works, and as far as I can tell, it is still the only recommended method to disable the gnome-keyring ssh component. Notice how we also configure GnuPG’s gpg-agent to enable SSH daemon support.
Topics for further discussion and research this time around includes:
Should scdaemon (and possibly pcscd) be pre-installed on Debian desktop systems?
Could gpg --card-status attempt to import the public key and secret key stub automatically? Alternatively, some new command that automate the bootstrapping of a new smartcard.
Should GNOME keyring support smartcards?
Why is GNOME keyring used by default for SSH rather than gpg-agent?
Should gpg-agent default to enable the SSH daemon?
What could be done to automatically infer the trust setting for a smartcard based private key?
