OS X 10.11 - Clients not connecting to site with Let's Encrypt certificates

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+1. Eventually, as devices age, you'd need to upgrade them unfortunately.

If you want macOS older support, probably using acme.sh client and switching to ZeroSSL SSL certificate might help as it has a cross signed AAA Certificate Services CA root certificate which was added to macOS 10.4 so old enough to support it. That's one suggestion I have for my users, switch to ZeroSSL https://blog.centminmod.com/2021/10/02/2425/centmin-mod-managing-letsencrypt-dst-root-ca-x3-certificate-expiration-on-centos-7/

The USERTrust RSA/ECC and COMODO RSA/ECC CA roots were added to the following devices since:

Apple :

  • macOS Sierra 10.12.1 Public Beta 2
  • iOS 10

Microsoft :

  • Windows XP (via Automatic Root Update; note that ECC wasn’t supported by Windows until Vista)
  • Windows Phone 7

Mozilla :

  • Firefox 3.0.4 (COMODO ECC Certification Authority)
  • Firefox 36 (the other 3 roots)

Google :

  • Android 2.3 (COMODO ECC Certification Authority)
  • Android 5.1 (the other 3 roots)

Oracle :

  • Java JRE 8u51

Opera :

  • [Browser release on December 2012]

360 Browser :

  • SE 10.1.1550.0 and Extreme browser 11.0.2031.0

And the cross-signed AAA Certificate Services root provides compatibility to older devices:

  • Apple iOS 3.
  • Apple macOS 10.4.
  • Google Android 2.3.
  • Mozilla Firefox 1.
  • Oracle Java JRE 1.5.0_08.
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