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.


3 thoughts on “Use Let’s Encrypt Certificates with FreeRADIUS”

  1. Thanks for the guide! I tried this for my home setup, just to have means to present trusted certificates to the clients, which “looks better” and does not educate the kids to accept untrusted certs. Since I have letsencrypt certs anyhow, it was quite easy. However, even after adding the subdomain of the machine running freeradius to the letsencrypt cert, the iOS devices here here still call the presented cert “untrusted”. Any way to get this “fixed”? If not, probably better to go with the more secure, self signed option.


    1. I’m afraid not. I believe the default behavior of iOS is to always present the server cert to the user and require them to accept it, even if it is a valid cert (unless it has been preinstalled in an MDM configuration profile). This is a downside to using LE with a heavy iOS environment as each time the cert is renewed, clients have to accept it again.


      1. Thanks. I could live with the renewal periods and repeated confirmation. The point I was surprised about is that iOS calls the certificated “not trusted”, in red at the top. That’s more or less identical to how the private, self-signed certificates were presented…


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