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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.

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

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