Use Let’s Encrypt Certificates with FreeRADIUS


Let’s Encrypt is a certificate authority that generates TLS certificates automatically, and for free. It’s been great for web server administrators because it allows them to automate the process of requesting, receiving, installing, and renewing TLS certificates, taking the administrative overhead out of setting up a secure website. And did I mention it’s free and supported by all the major web browsers now?

Getting all of that to work with a RADIUS server is challenging however, mostly because of the way Let’s Encrypt works. The Let’s Encrypt client runs on a web server with a public domain name. The client requests a TLS cert from Let’s Encrypt and before Let’s Encrypt issues the cert, it verifies that the client is connecting from the same domain name that it is requesting a cert for, and that the client can put some hidden files on the server’s website. Do you see the problem? Unless you run a public-facing web server on your RADIUS server (unlikely), Let’s Encrypt will not issue certs to your server. It needs a web server it can interact with in order to validate the domain name of the client’s request.

Why use a certificate from a public CA like Let’s Encrypt for 802.1X/PEAP authentication? While a private CA offers more security, a public CA has the advantage of having a pre-installed root certificate on virtually all RADIUS supplicants, including BYOD clients that are unmanaged. If you don’t have an MDM or BYOD onboarding solution, you can’t get your private root cert onto BYOD clients very easily.

Unmanaged clients are a security risk, however, because the end-user can easily override security warnings that occur when connecting to an evil twin network with a bogus cert. A good MDM solution will allow network admins configure BYOD clients properly so that TLS failures cannot be bypassed.

A few considerations before you get too excited:

  • Again, a better, more secure solution is to use a private CA and distribute the RADIUS server cert to clients using an MDM solution and/or BYOD onboarding solution.
  • Let’s Encrypt certs are only good for three months at a time, and some supplicants will prompt users to accept the new certificate when it is renewed.
  • Build in some error handling, logging, and notification. E.g. an email from the web server when the cert renewal routine runs, including its output, and an email from the RADIUS server when it copies the new certs and reloads FreeRADIUS.
  • It works as root, but there’s probably a way to accomplish this without using root. Do it that way.
  • You can accomplish the same thing with Windows servers and Powershell.
  • You broke it, not me.

To get this working, we need a public web server with the same domain same as you’d use in your RADIUS server’s cert common name. This means internal domain names with a .local TLD won’t work.

I setup two Ubuntu servers, one running the nginx web server with a public IP, and another on my local network running FreeRADIUS. The web server will run the Let’s Encrypt client and create and renew the certs. The RADIUS server will copy those certs from the web server and use them for PEAP authentication. Once setup, the process of renewing and installing the certs on the RADIUS server happens automatically, just like it would on a web server.

First, a public DNS A record needs to be setup with the domain name which will be used on the TLS cert common name, we’ll use, and point it to the IP address of the web server.

Once that is done, you can install and run the Let’s Encrypt client on the web server. It works with Apache too, but if you prefer nginx like me, follow these directions to get it setup with Ubuntu 14.04 or Ubuntu 16.04. Don’t skip over the part about using cron to run the renewal routine.

Now that we have the certs on the web server, we’ll turn our attention to the RADIUS server. The first thing we need to do is setup ssh public key authentication between the two servers. I used the root account on both servers to do this, so that I would have permissions everywhere I needed it. With public key authentication in place securely copying the certs in the future can happen automatically, without getting stopped by a password request. Here are instructions to get that working.

Now we’ll start configuring FreeRADIUS on the RADIUS server. I’m assuming you already have a working FreeRADIUS server. I’m using FreeRADIUS 3, and you should be too. I like to use a separate directory for the Let’s Encrypt certs.

root@freeradius:~# mkdir /etc/freeradius/certs/letsencrypt/

Now let’s try copying the certs from the web server to this directory on the RADIUS server. If public key authentication is working, you should not be prompted for a password.

root@freeradius:~# scp /etc/freeradius/certs/letsencrypt/
root@freeradius:~# scp /etc/freeradius/certs/letsencrypt/

Did it work? If so, you should see the certs in the new folder we created.

root@freeradius:~# ls /etc/freeradius/certs/letsencrypt/
fullchain.pem  privkey.pem

Now we need to configure FreeRADIUS to use the Let’s Encrypt certs for PEAP authentication. I have a previous blog about using different CA’s for PEAP and EAP-TLS on FreeRADIUS that should come in handy here. If you are using EAP-TLS too, be sure not to change that CA from your private CA! All we need to do now is modify /etc/freeradius/mods-enabled/eap with our new certs in the TLS section used for PEAP.

root@freeradius:~# nano /etc/freeradius/mods-enabled/eap

tls-config tls-peap should be changed to:

tls-config tls-peap {
 private_key_file = ${certdir}/letsencrypt/privkey.pem
 certificate_file = ${certdir}/letsencrypt/fullchain.pem

If you aren’t using multiple TLS configurations, this section is named tls-config tls-common. You can leave it like that.

Reload FreeRADIUS for the change to take effect.

root@freeradius:~# service freeradius reload
 * Checking FreeRADIUS daemon configuration...               [ OK ] 
 * FreeRADIUS daemon is running
 * Reloading FreeRADIUS daemon freeradius                    [ OK ]

Now when connecting to the WLAN that is configured to use this RADIUS server for 802.1X/PEAP  authentication, the client is presented with a valid Let’s Encrypt server certificate.


OK, we have a working FreeRADIUS server using Let’s Encrypt certs for 802.1X/PEAP authentication. Now let’s automate the process of getting renewed certs from the web server to the RADIUS server. We’ll use scp and cron to get this done.

On the RADIUS server, add these commands to root’s crontab, with the appropriate domain names.

root@freeradius:~# crontab -e
# m h dom mon dow command
0 3 * * 1 scp /etc/freeradius/certs/letsencrypt/
0 3 * * 1 scp /etc/freeradius/certs/letsencrypt/
5 3 * * 1 service freeradius reload

At 3:00 AM every Monday, cron will run copy the TLS certs from the web server the reload FreeRADIUS at 3:05 AM to put them into production. Now the Let’s Encrypt certs are automatically installed on the RADIUS server a few minutes after they are renewed on the web server. The certs are good for three months at a time and renewable one month in advance, so you’ll get renewed certs automatically installed every two months.

Presto! You now have Let’s Encrypt certs automatically renewed and installed on your RADIUS server. While a private CA is a better solution for 802.1X authentication, this isn’t bad for a $0 software stack.

Hardening TLS for WLAN 802.1X Authentication

encryption_lockThis post outlines some configuration changes which can enhance the security of 802.1X EAP methods PEAP and EAP-TTLS, which use a temporary layer 2 TLS tunnel to protect a less secure inner authentication method. While EAP-TLS doesn’t create a full TLS tunnel, it does use a TLS handshake to provide keying material for the four-way handshake. It needs strong TLS too.

Standard 802.1X security best practices should also be implemented such as using strong passwords, disabling insecure EAP methods, disabling TKIP, proper supplicant configuration, deploying sha-2 certificates, and anonymous outer usernames. The focus here is the TLS tunnel exclusively.

Not all RADIUS servers can implement all of these suggestions, but some can certainly do more than others. My experience has been with Microsoft NPS and FreeRADIUS servers so that is what I’ll refer to when discussing specific implementations. I welcome input from Aruba ClearPass and Cisco ISE administrators on configuring those servers as well.

Why go through all the trouble? It turns out the same encryption techniques that are used by web clients and servers to protect data in HTTPS sessions are also used when EAP methods rely on a TLS encrypted session. Ask any web server admin, and they’ll tell you that not all HTTPS is created equally. The same vulnerabilities that web server admins deal with exist in TLS-assisted EAP methods used on the WLAN as well. There is a lot to be learned from the TLS best practices that are recommended for web server admins.

At the end of the day, the TLS session is all that stands between user credentials and would-be hackers. It needs careful consideration to verify that it is meeting current security standards.

Here’s what to do.

Disable SSL

We’re talking specifically about SSLv2 and SSLv3 here, not TLS, the collection of which is often referred to simply as “SSL.” SSLv2 and SSLv3 were cracked long ago.

Consider TLS Methods

TLS 1.2 is the most secure TLS method available, so why not disable TLS 1.0 and TLS 1.1? Right now supplicant support for TLS 1.1 and TLS 1.2 is far from universal, and TLS 1.0 with strong ciphers is still considered secure. Keep TLS 1.0 enabled for now.

Disable Weak Cipher Suites

Cipher suites are the specific encryption algorithms that are used in a TLS session. Supplicants and servers support a broad range of them, and some of them are better than others. Many RADIUS servers have older insecure cipher suites enabled by default. This allows old supplicants that do not support newer cipher suites to still function. Unless you have older supplicants, you can disable many of these cipher suites to enhance 802.1X security.

A current listing of strong cipher suites can be found at While the website focuses on web server configuration, TLS is TLS.

Be aware that EAP-TLS requires TLS_RSA_WITH_3DES_EDE_CBC_SHA.

Microsoft NPS

Microsoft NPS relies on Schannel to provide encryption for TLS-tunneled EAP methods. In order to control the protocols Schannel uses, an administrator must alter these registry keys. Note that changing these keys affects all TLS functionality on the server, so if you run IIS or RDS with TLS, these changes will affect those applications as well. Proceed with caution. The registry keys can be found in:


A full listing of cipher suites supported by Schannel can be found here.

If the prospect of manually editing dozens of registry keys on a Windows Server doesn’t appeal to you, the good people at Nartac Software have developed an application that allows these changes to be managed in a user-friendly GUI interface. IIS Crypto allows you to make all of the registry settings necessary for this, while also including some handy templates including Best Practices, PCI, FIPS 140-2, and Defaults.

Here is IIS Crypto displaying the default Schannel configuration of a Windows Server 2012 R2 server. There is a lot not to like here…


And here is the Best Practices template. Note the obsolete protocols and cipher suites that are disabled, and the order in which cipher suites are prefered is updated as well.


Be aware that manually taking control of the Schannel TLS configuration means you’re in charge of it going forward. If Microsoft updates the default configuration, your manual config may still be in place. Stay up-to-date on new TLS vulnerabilities and periodically review your configuration for needed changes.


FreeRADIUS 3 is the current supported stable release and you should be thinking about upgrading to it if you have not already. SSLv2 and SSLv3 are not supported by FreeRADIUS 3, only TLS 1.0, TLS 1.1, and TLS 1.2.

For FreeRADIUS to require stronger cipher suites, add this to the EAP-TLS configuration in the “eap” configuration file. Alternatively, specify a colon-separated list of specific cipher suites.

cipher_list = "HIGH"

Also be aware that  FreeRADIUS 2.2.6 and 3.0.7 and contain a critical bug that prevents successful TLS 1.2 sessions from starting. You should update these servers as soon as possible.

Harden Supplicants Too

Few 802.1X supplicants allow you to alter their TLS configuration. The best thing to do with supplicants is to routinely install system updates and retire clients that are EOL.

Documentation for the TLS capabilities of client supplicants is hard to come by. Microsoft published an update to Windows 7 and above to allow the use of TLS 1.1 and TLS 1.2 in its 802.1X supplicant, if configured manually for now. wpa_supplicant for Linux supports TLS 1.2 in version 2.0 and version 2.6 enabled it by default. TLS 1.2 is the default TLS version used in the supplicants for Windows 10Mac OS 10.11, iOS 9, and Android 6.0 (Update: It appears that Apple has deferred their decision to default to TLS 1.2 in iOS 9/ Mac OS 10.11 until a later release).

Lab it Up

To know definitively what a client supplicant is capable of, run a packet capture on TLS-tunneled EAP authentication and observe the TLS negotiation frames, or TLS handshake, that occur right after 802.11 association and EAP identity request/response frames.

The client will send a “Client Hello” frame in which Wireshark will mark as a TLS protocol frame. This frame includes the TLS version requested by the client along with its supported cipher suites. The TLS version is the highest version the client supports.


Next, the RADIUS server will respond with a “Server Hello” frame which specifies the TLS version and cipher suite to be used during the TLS session, and includes the server certificate as well. The server will choose the best cipher suite that both client and server support and the highest TLS version that both support as well.


A few more frames are exchanged to setup the TLS session, and then EAP authentication takes place within the encrypted TLS session. It’s these first two frames that are of most concern when documenting client TLS capabilities.

This is also a useful technique to use to verify that highly secure TLS encryption is occurring in production.