MacOS – How to bypass “this connection is not private” warnings in safari

So, as noted in the update, Safari does actually warn you -- once.

If you decide to proceed anyway, then for the remainder of that browser session, you need to remember that you're talking to a potentially compromised server, because you will see no evidence of that except by examining the certificate (by clicking on the https/padlock icon).

However, exiting Safari and restarting it restores the warning. A visit to the compromised site in the new instance of the browser once again presents the warning.

You need to import the cert via Server.app; that'll add it to the System keychain and several other locations that allow non-keychain-aware services to use it. I'm not sure why it'd be hanging, but I can think of a few things to try:

• If it's not a self-signed certificate, you probably need to import the appropriate intermediate certificate(s) by dragging them into the "Drag extra non-identity certificates here" section of the import dialog. If it's a DigiCert certificate, you can find their intermediate certs here. There's probably also a way to export this from the Windows server, but I'm not familiar enough with it.

• It's possible Server.app is getting confused by the file extension. Try renaming it from .pfx to .p12 (they both refer to the same file format, PKCS #12).

• There might also be something odd about the file contents. Since it sounds like it imports ok via Keychain Access, try importing it with that, then re-exporting it to .p12 (see the instructions you linked), then delete it from the keychain (to avoid a conflict) and re-import it with Server.app. It's possible importing and exporting with Keychain Access will clean up the file and make it work properly in Server.app as well.