How to create /etc/certificates/*.{cert,chain,concat,key}.pem files without reboot? I am trying to move from Comodo to Let's Encrypt certificates on OS X Server (10.7).
Something in Apple's server.app and ServerAdmin.app is broken. I can see and select newly imported certificates in server.app but after a few seconds and re-opening the dialog the selected certificates are back to the original value. In &quot;Server Admin&quot; &gt; Mail &gt; Advanced tab I can select the new certificates and they stick. However the imap and smtp services still use the old certificate.
I see that for the old certificate there are 4 files in /etc/certificates/: host.domain.tld.SHA1.{key,cert,chain,concat}.pem
I know that the only the old certificate is in /etc/certificates/ because SHA1 of the new certificate, looked up with:
$ openssl x509 -in host.domain.tld.cer -noout -fingerprint -sha1 | cut -f2 -d'=' | sed 's/://g' 

, is showing a different SHA1.
Security import
According to certbot4osx source code, it looks like the security import host.domain.tld.cer -k /Library/Keychains/System.keychain command should

import the certificate into the system keychain, and
create the /etc/certificates/$1.$SHA_NEW.cert.pem

Reboot
After a reboot only 3 files: .cert, .chain and .concat, are there in /etc/certificates/, not .key. Other times all 4 required files are in /etc/certificates/ after the reboot.
CertsKeychainMonitor
I suspect that the CertsKeychainMonitor plugin is involved in .pem files creation. This as daemon started via com.apple.UserEventAgent-System.plist. Because Console lists at the second of the .pem file :

UserEventAgent: CertsKeychainMonitor: ready to process keychain &amp;
timer events.

How to always get all 4 (Let's Encrypt) certificate files correctly in /etc/certificates/ and without reboot?
1. Also import the .fullchain
Beside the .cer file also import the corresponding .fullchain file into the keychain, like
$ sudo /usr/bin/security -v import /Users/user/letsencrypt/fullchain.cer -k &quot;/Library/Keychains/System.keychain&quot;

2. Unload and load UserEventAgent-System
$ sudo /bin/launchctl unload /System/Library/LaunchDaemons/com.apple.UserEventAgent-System.plist; sudo /bin/launchctl load /System/Library/LaunchDaemons/com.apple.UserEventAgent-System.plist

3. Wait
About 1-2 minutes for the 4 certificate files to correctly appear in /etc/certificates/