In order to fix the following error after setting up SIP TLS in Asterisk 16.2:

asterisk[8691]: ERROR[8691]: tcptls.c:966 in __ssl_setup: TLS/SSL error loading cert file. <asterisk.pem>

I created a Let's Encrypt certificate using certbot:

apt install certbot
certbot certonly --standalone -d hostname.example.com

To enable the asterisk user to load the certificate successfuly (it doesn't have permission to access the certificates under /etc/letsencrypt/), I copied it to the right directory:

cp /etc/letsencrypt/live/hostname.example.com/privkey.pem /etc/asterisk/asterisk.key
cp /etc/letsencrypt/live/hostname.example.com/fullchain.pem /etc/asterisk/asterisk.cert
chown asterisk:asterisk /etc/asterisk/asterisk.cert /etc/asterisk/asterisk.key
chmod go-rwx /etc/asterisk/asterisk.cert /etc/asterisk/asterisk.key

Then I set the following variables in /etc/asterisk/sip.conf:

tlscertfile=/etc/asterisk/asterisk.cert
tlsprivatekey=/etc/asterisk/asterisk.key

Automatic renewal

The machine on which I run asterisk has a tricky Apache setup:

• a webserver is running on port 80
• port 80 is restricted to the local network

This meant that the certbot domain ownership checks would get blocked by the firewall, and I couldn't open that port without exposing the private webserver to the Internet.

So I ended up disabling the built-in certbot renewal mechanism:

systemctl disable certbot.timer certbot.service
systemctl stop certbot.timer certbot.service

and then writing my own script in /etc/cron.daily/certbot-francois:

#!/bin/bash
TEMPFILE=`mktemp`

# Stop Apache and backup firewall.
/bin/systemctl stop apache2.service
/usr/sbin/iptables-save > $TEMPFILE

# Open up port 80 to the whole world.
/usr/sbin/iptables -D INPUT -j LOGDROP
/usr/sbin/iptables -A INPUT -p tcp --dport 80 -j ACCEPT
/usr/sbin/iptables -A INPUT -j LOGDROP

# Renew all certs.
/usr/bin/certbot renew --quiet

# Restore firewall and restart Apache.
/usr/sbin/iptables -D INPUT -p tcp --dport 80 -j ACCEPT
/usr/sbin/iptables-restore < $TEMPFILE
/bin/systemctl start apache2.service

# Copy certificate into asterisk.
cp /etc/letsencrypt/live/hostname.example.com/privkey.pem /etc/asterisk/asterisk.key
cp /etc/letsencrypt/live/hostname.example.com/fullchain.pem /etc/asterisk/asterisk.cert
chown asterisk:asterisk /etc/asterisk/asterisk.cert /etc/asterisk/asterisk.key
chmod go-rwx /etc/asterisk/asterisk.cert /etc/asterisk/asterisk.key

# Commit changes to etckeeper and restart asterisk.
pushd /etc/ > /dev/null
/usr/bin/git add letsencrypt asterisk
DIFFSTAT="$(/usr/bin/git diff --cached --stat)"
if [ -n "$DIFFSTAT" ] ; then
    /usr/bin/git commit --quiet -m "Renewed letsencrypt certs." letsencrypt asterisk
    echo "$DIFFSTAT"
    /bin/systemctl restart asterisk.service
fi
popd > /dev/null