Paranoid Penguin - Linux VPNs with OpenVPN, Part IV

Use dangerous local-area networks without fear with OpenVPN.
Certificate/Key-Related Directives

Next, there are five directives related to helper files that OpenVPN will need to read in order to build a tunnel. ca specifies a file containing at least one Certificate Authority certificate, specifically, the certificate of whatever CA will have signed the OpenVPN's server certificate. If you try to connect to a server whose server certificate was not signed by a CA key/certificate specified here, your OpenVPN client process will terminate the connection.

cert specifies a file containing a client certificate for your OpenVPN client process to present to the OpenVPN server. This certificate needs to have been signed by a CA whose certificate resides in the server's ca file, or the server will reject connections from you.

In many if not most cases, the simplest way to handle these certificates is to use the same CA to create and sign both server and client certificates. In fact, if you remember Part II in this series (LJ, March 2010), I already created a client certificate and key, right after I created the server credentials.

Because this process is both important and simple, let's take a minute to review it. I'm skipping the process of setting up and creating the Certificate Authority itself, as that applies only to server setup (you should do that only once, on the server). So, assuming you've got a working CA set up on your OpenVPN server as described in Part II of this article, follow these steps to use OpenVPN's pkitool script to create a new client certificate:

1) su to root:

bash-$ su

2) Change your working directory to /etc/openvpn/2.0:

bash-# cd /etc/openvpn/2.0

3) Declare some PKI-related environment variables stored in the file vars:

bash-# source ./vars

4) Create the new certificate:

bash-# ./pkitool --pass minion

In step 4, the string minion is the name (the “common name”, in x.509 parlance) of the host or user whose certificate you're creating. After issuing this command, you'll be prompted twice to type the certificate's passphrase.

The output of this command takes the form of three files: ./keys/minion.csr, ./keys/minion.crt and ./keys/minion.key. Only the last two are important for the purposes of this article: the new client certificate and client key, respectively.

Of the helper files related to crypto that were created when you set up the OpenVPN server, your client certificate and key are the only two unique to the client; ca.crt and ta.key are used on the server and on all clients that connect to it. Note also that although the client certificate (minion.crt) contains no private data, the client key minion.key and the TLS authentication key ta.key both should be kept secret through local file permissions and by handling them carefully.

For example, you should never e-mail any client key or TA key in clear text (note that using an https:// URL for Webmail access doesn't count as message encryption). You should use S/MIME or PGP e-mail encryption if you need to mail keys to users.

If you use a USB drive or other physical media to distribute keys, you should either deliver it in person or use a trusted courier to deliver it, and users should be instructed either to destroy or erase the media after installing their keys, or keep the media under lock and key. Although having a passphrase-protected client key should make it hard for an attacker to use an intercepted key file, it's no guarantee! Under no circumstances should you issue blank-passphrase client certificates for any VPN scenario.

Speaking of the client key's passphrase, you also should take care in how you transmit that passphrase to the key's user. Because it isn't good policy for any system administrator to know users' passphrases in any context, users may afterward want to change the key's passphrase. The simplest way for users to do so is via the openssl command, like so:

bash-$ openssl rsa -in minion.key -out minion.key -aes192

The user does not need to be root to do this, provided the proper file permissions are set on minion.key (users should have read/write access on their own keys). After entering this command, users will be prompted for the key file's old passphrase and then twice for the new passphrase.

Once users have copied the files ca.crt, client.crt, client.key and ta.key over to their client system's /etc/openvpn/ directory, they should make sure they have the correct file permissions set. The two .crt files should be world-readable, but only owner-writable (that is, -rw-r--r--). The two .key files, however, should be only owner-readable/writable (that is, -rw-------).

All four files should be owned by root, assuming your users have root on their own Linux systems. (Setting up OpenVPN for nonroot users and the security challenges of doing so are beyond this article's scope.)

Now that you're clear on how to generate and manage client certificate/key pairs, let's continue working our way down Listing 2. The ca, cert and key directives specify the paths of your CA key file, client certificate file and client key file, respectively. In Listing 2 the values for these parameters are all just filenames, without their full paths specified. This implies that those three files are in the same directory as the client configuration file itself.

So, unlike on the server, where I left all the certificates and keys in /etc/openvpn/2.0/keys and, therefore, specified a CA certificate path of 2.0/keys/ca.crt, on the client system, you can get by with simply ca.crt if the file ca.crt, like the configuration file client.ovpn, is kept in the directory /etc/openvpn/.

The ns-cert-type server directive says what type of certificate your client should accept. Because in this example I'm dealing with multiple clients connecting back to a server, in Listing 2, it's set to server. This will prevent some other client from impersonating the server in a man-in-the-middle attack; the server's certificate, while signed by the same CA as its clients, has attributes that identify it as a server certificate, not another client certificate.

The last directive in the certificate/key-file portion of Listing 2 is tls-auth ta.key 1, which tells OpenVPN to use the file ta.key to add an extra layer of authentication on your VPN tunnel by requiring all packets in the TLS handshake phase at the beginning of each tunnel session to be signed with the specified TLS Authentication key. After the name of the TLS Authentication key (ta.key), specify a number telling in which “direction” to use this file: “0” for the server and “1” for clients.


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