Enrolling pre-10.10 devices

[puninskiya]

Hey guys,
we've switched to JAMF and unexpectedly have trouble enrolling a couple of pre-10.10 devices. Errors seem to be macOS version specific and occur on multiple devices.
After installing quickadd.pkg on 10.9.5 we get following:

1095dev:~ root# jamf enroll -prompt
dyld: Library not loaded: /System/Library/Frameworks/CoreBluetooth.framework/Versions/A/CoreBluetooth
  Referenced from: /usr/local/bin/jamf
  Reason: image not found
Trace/BPT trap: 5

Installing jamf executable on 10.8.5 gets us cert error:

1085dev:~ root# jamf enroll -prompt
JSS Username:
JSS Password:
SSH Username:
SSH Password:
Downloading required CA Certificate(s)...

There was an error.

     Error enrolling computer: Unable to establish trust with the JSS - Connection failure: "An SSL error has occurred and a secure connection to the server cannot be made."

Both errors don't occur on newer devices, and 10.10 and above enroll without any problems whatsoever. Any ideas on what could be causing this?

Greetings,
Alexey

[bentoms]

@puninskiya Is this an on-prem jamf install?

[puninskiya]

@bentoms Yep, it is.

[Look]

The certificate issue can probably be bypassed/solved by the certificate requirements under Security in the JSS to "Always except during enrollment".

[puninskiya]

I’ve solved the 1.8.5 issue – the cause was our certificate hardening. 10.8.5 only supports TLS 1.0 which is pretty unsecure by today’s standards. Still looking into the 10.9.5 issue.

[JasonAtCSUMB]

There is a bug related to 10.9.5 Macs. Jamf binary won't run any policies or even recon. You have to set up a symbolic link for CoreBluetooth.frameworks:

sudo /bin/ln -s /System/Library/Frameworks/IOBluetooth.framework/Frameworks/CoreBluetooth.framework /System/Library/Frameworks/CoreBluetooth.frameworks

[mschroder]

@puninskiya Did you check the minimum macOS required for clients for the JamfPro version you use? I think you have to use quite an old version of Jamf Pro if you want to use 10.8.5 macOS clients.