See also Zimbra Self-Signed SSL Certs

Howto: https://wiki.zimbra.com/wiki/Installing_a_LetsEncrypt_SSL_Certificate

Certbot logs to /var/log/letsencrypt/letsencrypt.log.

If you have trouble reissuing a new cert, or if Zimbra won't start, recreate and deploy a new self-signed cert to get Zimbra 'working' again. Then re-implement a LetsEncrypt cert.

If a cert is expired, you must reissue a new cert.

If a certificate renewal fails, try reissuing a new cert instead.

If you get an error “pkcs12: Unrecognized flag propquery”, see: https://community.zextras.com/forum/postid/7321/

#!/bin/bash
#
# /etc/cron.daily/letsencrypt-zimbra
#
# Modification for SAN certificate with multiple hostnames
# This may/will need to be adjusted for hostnames and possibly cert name
# If you followed the howto above using just the actual hostname, it will look like this
#
/usr/local/sbin/certbot certonly --cert-name zimbra2.yourdomain.tld -d zimbra2.yourdomain.tld -d zimbra.yourdomain.tld --standalone --manual-public-ip-logging-ok -n --preferred-chain  "ISRG Root X1" --agree-tos --register-unsafely-without-email
#
# Modification to test if cert was changed then exit script
if grep "not yet due for renewal" /var/log/letsencrypt/letsencrypt.log; then
   exit 0
fi
#
cp "/etc/letsencrypt/live/zimbra.yourdomain.tld/privkey.pem" /opt/zimbra/ssl/zimbra/commercial/commercial.key
chown zimbra:zimbra /opt/zimbra/ssl/zimbra/commercial/commercial.key
wget -O /tmp/ISRG-X1.pem https://letsencrypt.org/certs/isrgrootx1.pem.txt
rm -f "/etc/letsencrypt/live/zimbra.yourdomain.tld/chainZimbra.pem"
cp "/etc/letsencrypt/live/zimbra.yourdomain.tld/chain.pem" "/etc/letsencrypt/live/zimbra.yourdomain.tld/chainZimbra.pem"
cat /tmp/ISRG-X1.pem >> "/etc/letsencrypt/live/zimbra3.virtualarchitects.com/chainZimbra.pem"
chown zimbra:zimbra /etc/letsencrypt -R
cd /tmp

su zimbra -c '/opt/zimbra/bin/zmcertmgr deploycrt comm "/etc/letsencrypt/live/zimbra.yourdomain.tld/cert.pem" "/etc/letsencrypt/live/zimbra.yourdomain.tld/chainZimbra.pem"'

# Restart Zimbra after deploying cert
su zimbra -c '/opt/zimbra/bin/zmcertmgr deploycrt comm "/etc/letsencrypt/live/zimbra.yourdomain.tld/cert.pem" "/etc/letsencrypt/live/zimbra.yourdomain.tld/chainZimbra.pem"' && su zimbra -c '/opt/zimbra/bin/zmcontrol restart'

rm -f "/etc/letsencrypt/live/zimbra.yourdomain.tld/chainZimbra.pem"