It's possible importing and exporting with Keychain Access will clean up the file and make it work properly in Server.app as well. p12 (see the instructions you linked), then delete it from the keychain (to avoid a conflict) and re-import it with Server.app. Since it sounds like it imports ok via Keychain Access, try importing it with that, then re-exporting it to. There might also be something odd about the file contents. Most any IT system administrator can create certificates without having to be a PKI expert. Creating a trusted X.509 certificate on Apple’s MacOS (as well as Linux) is fast and simple using CertAccord Enterprise. p12 (they both refer to the same file format, PKCS #12). CertAccord© How To Create Trusted Certificates From Command Line On MacOS. It's possible Server.app is getting confused by the file extension. There's probably also a way to export this from the Windows server, but I'm not familiar enough with it. If it's a DigiCert certificate, you can find their intermediate certs here. 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. Apple has provided web developers with an enormously flexible development environment in Mac OS X. I'm not sure why it'd be hanging, but I can think of a few things to try: Web development requires the hardware and software to accommodate a wide variety of client needs and web technologies. 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.
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