Hardening PGP using GnuPG and Yubikey
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1 Hardening using GnuPG and Yubikey hybrid multifactor authentication and cryptography John Roman Linux System Administrator RAND Corporation SCALE 2017
2 101 public/private keyrings
3 101 public/private keyrings public keys go to the world, generated on machine
4 101 public/private keyrings public keys go to the world, generated on machine key types: signing, authentication, cryptography
5 pitfalls private keyring... but how private?
6 pitfalls private keyring... but how private? portability
7 pitfalls private keyring... but how private? portability standards compliance
8 conventional example, the CAC/PIV Common Access Card, in service since 2005
9 conventional example, the CAC/PIV Common Access Card, in service since 2005 FIPS201 PIV Federal Information Processing Standard (FIPS) 201,Personal Identity Verification
10 Open: we we re JUST thinking that! Open Card: in service since 2004
11 Open: we we re JUST thinking that! Open Card: in service since different vendors, multiple form factors
12 Open: we we re JUST thinking that! Open Card: in service since different vendors, multiple form factors relatively unknown outside of FSF Europe.
13 Our focus: Yubikey supports hybrid mode
14 Our focus: Yubikey supports hybrid mode hermetic, crushproof, scaleable pricing
15 Our focus: Yubikey supports hybrid mode hermetic, crushproof, scaleable pricing NFC option.
16 general concepts card has a CPU, firmware.
17 general concepts card has a CPU, firmware. keys are loaded into slots, or generated by the card
18 general concepts card has a CPU, firmware. keys are loaded into slots, or generated by the card encryption, decryption, signature are all commands
19 general concepts card has a CPU, firmware. keys are loaded into slots, or generated by the card encryption, decryption, signature are all commands once loaded, private keys are sacrosanct.
20 general concepts card has a CPU, firmware. keys are loaded into slots, or generated by the card encryption, decryption, signature are all commands once loaded, private keys are sacrosanct. Yubikey only accepts commands, only returns data. NEVER KEYS.
21 HSM Specific concepts pin number similar to european credit cards
22 HSM Specific concepts pin number similar to european credit cards 3 strikes, your pin is locked
23 HSM Specific concepts pin number similar to european credit cards 3 strikes, your pin is locked pin can be unlocked with a security officer pin.
24 HSM Specific concepts pin number similar to european credit cards 3 strikes, your pin is locked pin can be unlocked with a security officer pin. 3 strikes against the SO pin? card is bricked. keys lost. game over.
25 HSM Specific concepts pin number similar to european credit cards 3 strikes, your pin is locked pin can be unlocked with a security officer pin. 3 strikes against the SO pin? card is bricked. keys lost. game over. pin length 6-8 characters, some implementations more than 128 char.
26 placing the card into hybrid mode ykpersonalize -d -m82 Firmware version Touch level 527 Program sequence 3 The USB mode will be set to: 0x82 Commit? (y/n) [n]: n
27 Open card overview keys were loaded from an airgapped system using the keytocard command.
28 Open card programming gpg card-edit mode, admin commands enabled
29 applications anything GPG enabled
30 applications anything GPG enabled anything PAM enabled
31 applications anything GPG enabled anything PAM enabled defense in depth: OTP/Cert/PW? sure
32 applications anything GPG enabled anything PAM enabled defense in depth: OTP/Cert/PW? sure multiple cards per key, each has a unique subkey (code signing!)
33 applications
34 NFC option: here be dragons easy integration with Openkeychain in Android/IPhone
35 NFC option: here be dragons easy integration with Openkeychain in Android/IPhone keys need to be generated by the user
36 NFC option: here be dragons easy integration with Openkeychain in Android/IPhone keys need to be generated by the user only supports a 2048 bit key
37 deploying 450 (thousand?) of these things.
38 Entropy. GPG relies on kernel, not userland entropy. - Flying Stone FST01 from the FSF store! - RTL digital TV dongle and a tractor paper copy of phrack
39 Open not included... Red Hat Enterprise Linux 7 does not include opensc GnuPG
40 y tho... NFC user fatigue. not all NFC devices are great at picking up NFC lack of a yubikey might cause lack of communication.
41 destroyed cards... try not to trigger a SO/Reset pin lock!! to reissue or reset?
42 Questions?
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