My second article on using a smart card for storing the private key material of my own certificate authority. Published in the November 2011 issue of BSD Magazine.

What you will learn

  • How to use smart cards to store private keys
  • The use of OpenSSL with a different crypto provider

What you should know

  • Your way around a FreeBSD system
  • The basics of a PKI
  • Why you need a Certificate Authority


With the recent breaches of Certificate Authorities (Comodo, Diginotar) I wanted to take a closer look at the security of my own Certificate Authority (CA). This CA is used for identification and authentication of servers, clients and users in my home network.
The keys for certificates are typically stored in text files on the file system. Access to the disk will reveal the keys. An attacker can make a copy and start issuing certificates outside my control.
The primary design requirement is therefore that keys will never be accessible in plain text.

Hardware Security Module

Enter HSM, hardware designed to keep the private key private. They come in various forms, from an appliance / PCI cards to an USB token or smart card.PCI cards are typically encased in metal with features like automatic key deletion upon physical tampering. They are basically a dedicated computer running HSM software and using the PCI bus for interfacing with the host computer.
Appliances are typically these PCI cards in an enclosure providing networking and rudimentary user control.
HSM’s can also have the form of a single chip. These do not have their own power supply (for deleting keys), but are still a small computer running HSM software. They can be embedded on smart cards, in USB tokens or integrated in other systems like the TPM chip on your motherboard.

Design Choices

For my HSM I decided to use smart cards, because they are cheap, readily available and easy to experiment with.
The computer hardware is generic FreeBSD supported platform (i386 in my case, as I am working on putting it on an ALIX / NanoBSD installation). Attached is a Feitian SCR310 smart card reader (ftsafe-r310) and a Feitian PKI card (FTCOS / PK-01C).
This reader is cheap, but any supported reader is fine. This card was primarily chosen for its price and availability. It has lots (64k) of storage memory available, but a limitation of 2048 bits for RSA keysize. Please do your own research on the types of readers and cards to fit your requirements.
For my production system, I will move to a Gemalto USB TR reader. It has an adapter so it can be mounted in a 3.5” floppy bay.The software is a clean FreeBSD 8.2 with the following ports:
– /usr/ports/devel/libccid – interface for USB and serial smart card readers
– /usr/ports/security/opensc – tools for smart card managment (in PC/SC mode)
– /usr/ports/security/engine-pkcs11 – engine for PKCS11 support in OpenSSL
– /usr/ports/security/openssl – tools for certificate management (in this case)
Due to the many, many dependencies, it will take some time to install. All default settings for the ports are fine.

There is a number of different CA designs possible. From very flat (the root CA issues all certificates directly) to very hierarchical (various sub and sub-sub CA’s issue certificates on behalf of the root CA).
My design has one root CA with a sub CA per functional area. This is done for security reasons. First of all, the root CA only has to sign the sub CA’s. The use and exposure of the private key of the root CA is therefor very limited.
Next to that, the server sub CA never issues client certificates, so the VPN concentrator has to trust only the clients sub CA when validating certificates. Client certificates issued by the (possibly hacked) server- or user sub CA’s are not accepted.

Testing the setup

After the installation of the software, it is time to plugin the reader and test the setup. Insert the card in the reader and run

# opensc-tool --list-readers

# Detected readers (pcsc)
Nr.  Card  Features  Name
0    Yes             Feitian SCR310 00 00

The reader is recognized by the driver, let’s initialize the card by formatting it with a PKCS15 structure. PKCS 15 is a cryptographic token information format standard originally designed by RSA. ISO 7816-15 now manages the card-related parts of this standard.

# pkcs15-init --erase-card
# pkcs15-init --create-pkcs15 \
--profile pkcs15+onepin \
--auth-id 01 \
--pin 0000 \
--puk 123456 \
--label " PKI"

This specific card supports only one user-PIN, so the pkcs15+onepin profile is used. More advanced cards can offer more users and role separation.
The label is just a name to identify the card.
The PIN for the user (auth-id 01) is set to 0000. If you want to reset the PIN, you will need the PUK, which is set to 123456.

The card now has a PKCS15 structure and is able to store private keys and their certificates.

Importing keys

It is possible to have the card generate the private key, so it will never be available in plain text. This is the most secure option, but losing the card will also make the keys unrecoverable.
Because I already have a CA in place, I started with importing the existing keys. Generating the keys on the card will be discussed at the end of this article. Importing the key material (in PEM or PKCS12 format) is straightforward.

# pkcs15-init --verbose \
--store-private-key ewak.net_Sub_CA_servers.p12 \
--format pkcs12 \
--auth-id 01 \
--cert-label " Sub CA servers"

Using reader with a card: Feitian SCR310 00 00
Connecting to card in reader Feitian SCR310 00 00...
Using card driver entersafe.
Found PKI
About to store private key.
Importing 1 certificates:
0: /C=NL
/OU=Certificate Services
/ Sub CA servers
User PIN [User PIN] required.
Please enter User PIN [User PIN]:

The user PIN for auth-id 01 is defined during the initialization of the card, “0000” in this article. It can also be supplied to the pkcs15-init tool by adding the “–pin 0000” option. Now let’s see what is on the card.

# pkcs15-tool –dump

Using reader with a card: Feitian SCR310 00 00
PKCS#15 Card [ PKI]:
Version        : 0
Serial number  : 3021303609260511
Manufacturer ID: EnterSafe
Last update    : 20110925214004Z
Flags          : EID compliant

PIN [User PIN]
Object Flags   : [0x3], private, modifiable
ID             : 01
Flags          : [0x32], local, initialized, needs-padding
Length         : min_len:4, max_len:16, stored_len:16
Pad char       : 0x00
Reference      : 1
Type           : ascii-numeric
Path           : 3f005015

Private RSA Key [Private Key]
Object Flags   : [0x3], private, modifiable
Usage          : [0xC], sign, signRecover
Access Flags   : [0x0]
ModLength      : 2048
Key ref        : 1 (0x1)
Native         : yes
Path           : 3f005015
Auth ID        : 01
ID             : 53f70c3ea5be9aef27d959c134d8ebef77322786
GUID           : {53f70c3e-a5be-9aef-27d9-59c134d8ebef}

X.509 Certificate [ Sub CA servers]
Object Flags   : [0x2], modifiable
Authority      : no
Path           : 3f0050153100
ID             : 53f70c3ea5be9aef27d959c134d8ebef77322786
GUID           : {53f70c3e-a5be-9aef-27d9-59c134d8ebef}
Encoded serial : 02 01 02

The import was successful. The info for the PIN, the private key and the certificate are displayed. The ID of the private key is a number to record, as we will need it later to tell OpenSSL which key to use. A shorter command for retrieving this ID is

# pkcs15-tool –-list-keys

We can add more keys for other certificates. My card has three keys for signing server, client and user certificates.

OpenSSL and PKCS11

OpenSSL can be instructed to use an external crypto provider for generating and storing key material using the PKCS11 API, also known as Cryptoki.

When using OpenSSL, we can specify keys on the smart card instead of pointing to a local keyfile on the disk. To do this, we need the card’s slot and the key’s ID. The ID we found using the pkcs15-tool –list-keys command. The slot can be found with the pkcs11-tool command.

# pkcs11-tool --module /usr/local/lib/ --list-slots

Available slots:
Slot 0 (0xffffffff): Virtual hotplug slot
Slot 1 (0x1): Feitian SCR310 00 00
token label: PKI (User PIN)
token manuf:   EnterSafe
token model:   PKCS#15
token flags:   rng, login required, PIN initialized, token initialized
serial num  :  3021303609260511

Slot 1 is our card reader with the correct smart card (“ PKI”) inserted.

Now start an OpenSSL prompt and load the PKCS11 engine

# openssl
OpenSSL> engine dynamic \
-pre SO_PATH:/usr/local/lib/engines/ \
-pre ID:pkcs11 \
-pre LIST_ADD:1 \
-pre LOAD \
-pre MODULE_PATH:/usr/local/lib/

(dynamic) Dynamic engine loading support
[Success]: SO_PATH:/usr/lib/engines/
[Success]: ID:pkcs11
[Success]: LIST_ADD:1
[Success]: LOAD
[Success]: MODULE_PATH:/usr/local/lib/
Loaded: (pkcs11) pkcs11 engine

The engine is loaded and can be used by specifying it in OpenSSL commands with the following parameters
-engine pkcs11 \
-keyform engine \
-key slot_1-key_53f70c3ea5be9aef27d959c134d8ebef77322786

for example

OpenSSL> req -new -engine pkcs11 -keyform engine \
-key slot_1-key_ d893afddc82b28fb539e975b2a3e18efc2f3c474 \
-out cert.csr –text

PKCS#11 token PIN:
You are about to be asked to enter information that will be
incorporated into your certificate request.
-snip- OpenSSL output omitted –snip-

This will create a certificate signing request from the public key with the id shown.

The use of PKCS11 can be set in the OpenSSL configuration file by adding the following lines to your openssl.cnf configuration file

openssl_conf = openssl_init
engines = engine_section
pkcs11 = pkcs11_section
engine_id = pkcs11
dynamic_path = /usr/local/lib/engines/
MODULE_PATH = /usr/local/lib/
init = 1

All OpenSSL commands can now be run using the PKCS11 engine by specifying

-config /path/to/openssl.cnf –engine pkcs11 \
–keyform engine –key slot_<slot>-id_<id>

at the command line

Signing keys

To use the key for signing certificates,

# openssl ca -config /etc/ssl/openssl.cnf \
-engine pkcs11 \
-keyform engine \
-keyfile 1:53f70c3ea5be9aef27d959c134d8ebef77322786 \
-cert ewak.net_Sub_CA_servers.crt \
-in cert.csr -out cert.pem

Using configuration from /etc/ssl/openssl.cnf
engine "pkcs11" set.
PKCS#11 token PIN:
Check that the request matches the signature
Signature ok
Certificate Details:
-snip- OpenSSL output omitted –snip-
Sign the certificate? [y/n]:y

1 out of 1 certificate requests certified, commit? [y/n]y
Write out database with 1 new entries
Data Base Updated

The certificate is signed with the specified private key on the smart card. Note the different notation of the parameter for the key selection.

–keyfile <slot>:<key id>

OpenSSL will otherwise look for the keyfile specified in your openssl.cnf and fail to load.

Generating keys

If you do not have an existing PKI or are willing to change its private keys, you can have the keys generated by and stored on the smart card. The keys will never have touched you computer’s memory or file system. This is done with the pkcs15-init tool.

# pkcs15-init --generate-key rsa/1024 --auth-id 01

Using reader with a card: Feitian SCR310 00 00
User PIN [User PIN] required.
Please enter User PIN [User PIN]:

Both private and public keys are stored on the smart card. The key is an RSA key of 1024 bits length. This public key can now be used for generating a certificate signing request.

# pkcs15-tool --list-keys
Using reader with a card: Feitian SCR310 00 00
Private RSA Key [Private Key]
Object Flags   : [0x3], private, modifiable
Usage       : [0x4], sign
Access Flags   : [0x1D], sensitive, alwaysSensitive, neverExtract, local
ModLength   : 1024
Key ref     : 1 (0x1)
Native      : yes
Path        : 3f005015
Auth ID     : 01
ID          : d893afddc82b28fb539e975b2a3e18efc2f3c474
GUID        : {d893afdd-c82b-28fb-539e-975b2a3e18ef}

# openssl req -new \
-engine pkcs11 \
-keyform engine \
-key slot_1-key_d893afddc82b28fb539e975b2a3e18efc2f3c474 \
-out cert.csr –text

PKCS#11 token PIN:
You are about to be asked to enter information that will be
incorporated into your certificate request.
-snip- OpenSSL output omitted –snip-

The signed certificate can then be stored on the card using the pkcs15-init tool.

# pkcs15-init –-store-certificate cert.pem –-auth-id 01 \
--id d893afddc82b28fb539e975b2a3e18efc2f3c474

Using reader with a card: Feitian SCR310 00 00
User PIN [User PIN] required.
Please enter User PIN [User PIN]:

The –id is the identifier of the generated key.

Published in the November 2011 issue of BSD Magazine.



2 Responses to Equip your CA with a HSM for < 50 Euros

  1. Just a quick note that the Feitian R-301 and Feitian PKI smarcards can be purchased from our webstore: People writing free software can request a free token here:

  2. Versatile Security has a product called vSEC:ID Server Key that enables use of mini driver enabled smart cards as HSM. The product is perfectly suited for securing Microsoft Certificate Services. More details can be found here: