Mac OS X Server SSL Settings

The certificate you are using to provide SSL on your server is not issued by a certificate authority the Google recognises as valid. Most likely reason is that you are using a self-signed certificate generated within Server.app or Keychain.app. Another possibility is that you've bought the wrong certificate from a recognised authority.

If your server needs to be accessed by just you, tell your browser to accept it. If it's needed for a small workgroup you can generate an appropriate certificate authority and then push this to the clients. If you are providing e-commerce you need to pay $$$ to a recognised CA.

C.

So, it works fine with Safari, which is not Google Chrome. It seems to me that you need to ask about this in a Google Chrome forum.

C.

I would suggest replace the cert with a free cert from letsencrypt.org , you can find the automated process to do so at https://certbot.eff.org/#osx-apache

It will only require renewal every 3 months.