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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 "Server Admin" > Mail > 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

  1. import the certificate into the system keychain, and
  2. 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 & timer events.

How to always get all 4 (Let's Encrypt) certificate files correctly in /etc/certificates/ and without reboot?

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  • According to the .cert.pem file creation time (the seconds), I suspect that CertsKeychainMonitor is responsable for creating these 4 .pem files. Log states at creation time: "UserEventAgent: CertsKeychainMonitor: ready to process keychain & timer events." – Pro Backup Oct 14 '20 at 17:57
  • Two UserEventAgents are running, one as root user and one as logged in user. – Pro Backup Oct 14 '20 at 18:19
  • Near the next certificate renewal November 17th, I will try: sudo launchctl unload /System/Library/LaunchDaemons/com.apple.UserEventAgent-System.plist; sudo launchctl load /System/Library/LaunchDaemons/com.apple.UserEventAgent-System.plist – Pro Backup Oct 15 '20 at 9:39
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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 "/Library/Keychains/System.keychain"

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/

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